Name: 3663-79-4|Methyl 1,4-Benzodioxane-2-carboxylate|97%
Brand: Ambeed
SKU: A766360
Rating: 99 (22 reviews)

1
[ 67-56-1 ]
[ 3663-80-7 ]
[ 3663-79-4 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 1988 - 1996
[2]Tetrahedron Asymmetry,2003,vol. 14,p. 3779 - 3785

2
[ 1008-92-0 ]
[ 3663-79-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 98 percent / HOAc, conc. H₂SO₄ / H₂O / 15 h / 110 °C 2: 97 percent / conc. H₂SO₄ / 1 h / Heating

Reference： [1]Tomiyama; Wakabayashi; Yokota [Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1988 - 1996]

3
[ 3663-79-4 ]
5-[(3aS,4R,5R,6aS)-4-[(E)-(R)-3-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-3-hydroxy-propenyl]-5-hydroxy-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: 1) n-BuLi / 1) THF, hexane, -78 deg C, 30 min, 2) THF, 1.5 h 2: 1) NaH / 1) THF, 0 deg C, 2) THF, RT 3: NaBH₄ / methanol / 0 °C 4: HOAc / tetrahydrofuran; H₂O / 45 °C 5: KOH / methanol / 0 °C

Reference： [1]Tomiyama; Wakabayashi; Yokota [Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1988 - 1996]

4
[ 3663-79-4 ]
5-[(3aS,4R,5R,6aS)-4-[(E)-3-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-3-hydroxy-propenyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1) n-BuLi / 1) THF, hexane, -78 deg C, 30 min, 2) THF, 1.5 h 2: 1) NaH / 1) THF, 0 deg C, 2) THF, RT 3: NaBH₄ / methanol / 0 °C

Reference： [1]Tomiyama; Wakabayashi; Yokota [Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1988 - 1996]

5
[ 3663-79-4 ]
5-[(3aS,4R,5R,6aS)-4-[(E)-3-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-3-oxo-propenyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1) n-BuLi / 1) THF, hexane, -78 deg C, 30 min, 2) THF, 1.5 h 2: 1) NaH / 1) THF, 0 deg C, 2) THF, RT

Reference： [1]Tomiyama; Wakabayashi; Yokota [Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1988 - 1996]

6
[ 3663-79-4 ]
5-[(3aS,4R,5R,6aS)-4-[(E)-(S)-3-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-3-hydroxy-propenyl]-5-hydroxy-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 1) n-BuLi / 1) THF, hexane, -78 deg C, 30 min, 2) THF, 1.5 h 2: 1) NaH / 1) THF, 0 deg C, 2) THF, RT 3: NaBH₄ / methanol / 0 °C 4: HOAc / tetrahydrofuran; H₂O / 45 °C

Reference： [1]Tomiyama; Wakabayashi; Yokota [Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1988 - 1996]

7
[ 3663-79-4 ]
5-[(3aS,4R,5R,6aS)-4-[(E)-(R)-3-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-3-hydroxy-propenyl]-5-hydroxy-hexahydro-pentalen-(2E)-ylidene]-pentanoic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 1) n-BuLi / 1) THF, hexane, -78 deg C, 30 min, 2) THF, 1.5 h 2: 1) NaH / 1) THF, 0 deg C, 2) THF, RT 3: NaBH₄ / methanol / 0 °C 4: HOAc / tetrahydrofuran; H₂O / 45 °C

Reference： [1]Tomiyama; Wakabayashi; Yokota [Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1988 - 1996]

8
[ 120-80-9 ]
[ 3663-79-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 85 percent / K₂CO₃ / acetone / 12 h / Heating 2: 98 percent / HOAc, conc. H₂SO₄ / H₂O / 15 h / 110 °C 3: 97 percent / conc. H₂SO₄ / 1 h / Heating

Reference： [1]Tomiyama; Wakabayashi; Yokota [Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1988 - 1996]

9
methyl 15-(benzo[1,4]dioxan-2-yl)-15-oxo-9α,11α-di-(4-phenylbenzoyloxy)-16,17,18,19,20-pentanor-5-cis,13-trans-prostadienoate [ No CAS ]
[ 3663-79-4 ]
[ 54442-10-3 ]

Yield	Reaction Conditions	Operation in experiment
		2 EXAMPLE 2 The methyl 15-(benzo[1,4]dioxan-2-yl)-15-oxo-9α,11α-di-(4-phenylbenzoyloxy)-16,17,18,19,20-pentanor-5-cis,13-trans-prostadienoate used as starting material may be prepared as follows: Methyl benzo[1,4]dioxan-2-carboxylate was converted to dimethyl [2-(benzo[1,4]dioxan-2-yl)-2-oxo]ethylphosphonate by the process described in the second part of Example 1, b.p. 234°C. at 0.1mm./Hg, RF = 0.3 (50% ethyl acetate in toluene).

Reference： [1]Current Patent Assignee: ZIMPRO PASSAVANT ENVIRONMENTAL SYSTEMS - US3953502, 1976, A

10
[ 1729-67-5 ]
[ 120-80-9 ]
[ 3663-79-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate In acetone for 18h; Reflux;
74%	With potassium carbonate In acetone for 18h; Reflux;	4.5 Synthesis of (±)-methyl 1,4-benzodioxan-2-carboxylate 17a General procedure: A mixture of 12 g (0.11 mol) of catechol, 17.9 (0.1 mol) of methyl 2-bromopropionate, and 41.4 g (0.3 mol) of anhydrous K2CO3 was refluxed in 200 ml of dry acetone for 18 h. After the acetone was removed, the residue was taken up in methylene chloride, extracted with water, 5% NaOH, 5% HCl, and saturated NaCl solutions, and finally dried over anhydrous Na2SO4. Evaporation of the solvent and distillation of the residue afforded 15.4 g (74%) of 17a. Mp 60-62 °C [lit.23b mp 53 °C]; 1H NMR: δ 3.81 (s, 3H), 4.38 (d, J = 4.0 Hz, 2H,), 4.85 (t, J = 3.8, 7.6 Hz, 1H), 6.86-6.92 (m, 3H), 6.99-7.02 (m, 1H); 13C NMR: δ 52.78, 64.90, 72.05, 117.40, 121.98, 142.28, 169.48; HRMS (ESI) Calcd for C10H10NaO4 (M+Na): 217.0477. Found: 217.0474.
	Stage #1: benzene-1,2-diol With potassium carbonate In acetone for 0.25h; Reflux; Heating; Stage #2: Methyl 2,3-dibromopropionate With potassium carbonate In acetone for 1h; Reflux;	General procedure for the preparation of methyl3-substituted 1,4-benzodioxan-2-carboxylate (1a-1c): General procedure: To a solution of 1mol catechol in 1000 mL dry acetone was added 0.5 mol anhydrous potassiumcarbonate. The mixture was heated under reflux for 15 min, and then 0.25 molmethyl 2,3-dibromo ester (methyl2,3-dibromopropanoate, methyl 2,3-dibromobutanoate or methyl2,3-dibromo-3-phenylpropanoate: methyl 2,3-dibromo esters were obtained bytreating unsaturated esters with bromine)was added. Another 1.5 mol potassium carbonate and 0.75 mol methyl 2,3-dibromoester was added portionwise over 45 min. After the addition, refluxing wascontinued for 15 h. The cooled solution was filtered. The solvent was removedunder reduced pressure to give a residue. The residue was taken up in water andextracted with 300 mL × 3 ether. The extracts were washed with 5% NaOH anddried. Afterevaporating to dryness under reduced pressure, the residue was purified bycolumn chromatography, eluting with ethyl acetate/petroleum ether 1:50 (v/v).

Reference： [1]Yin, Xuguang; Huang, Yi; Chen, Ziyi; Hu, Yang; Tao, Lin; Zhao, Qingyang; Dong, Xiu-Qin; Zhang, Xumu [Organic Letters, 2018, vol. 20, # 14, p. 4173 - 4177]
[2]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[3]Wang, Songlin; Chen, Yin; Zhao, Song; Xu, Xiangqing; Liu, Xin; Liu, Bi-Feng; Zhang, Guisen [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 7, p. 1766 - 1770]

11
[ 3663-79-4 ]
UK-35494-27(S) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; butan-1-ol / 4 h / 25 °C / pH 7.1 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere 3.1: butan-1-ol / 4 h / Reflux 3.2: 50 °C
	Multi-step reaction with 3 steps 1.1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 0.33 h / 25 °C / pH 7.1 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere 3.1: butan-1-ol / 4 h / Reflux 3.2: 50 °C
	Multi-step reaction with 3 steps 1.1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 2 h / 25 °C / pH 7.1 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere 3.1: butan-1-ol / 4 h / Reflux 3.2: 50 °C

Reference： [1]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[2]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[3]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]

12
[ 3663-79-4 ]
UK-36528-27(R) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; butan-1-ol / 4 h / 25 °C / pH 7.1 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere 3.1: butan-1-ol / 4 h / Reflux 3.2: 50 °C
	Multi-step reaction with 3 steps 1.1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 2 h / 25 °C / pH 7.1 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere 3.1: butan-1-ol / 4 h / Reflux 3.2: 50 °C

Reference： [1]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[2]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]

13
[ 3663-79-4 ]
[ 687974-13-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 2 h / 25 °C / pH 7.1 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere 3: triethylamine / chloroform / 2 h / 0 °C / Inert atmosphere 4: chloroform / 6 h / Inert atmosphere
	Multi-step reaction with 4 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; butan-1-ol / 4 h / 25 °C / pH 7.1 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere 3: triethylamine / chloroform / 2 h / 0 °C / Inert atmosphere 4: chloroform / 6 h / Inert atmosphere

Reference： [1]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[2]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]

14
[ 3663-79-4 ]
[ 70918-54-6 ]

Yield	Reaction Conditions	Operation in experiment
42%		General procedure: Racemic methyl 1,4-benzodioxan-2-carboxylate 17a (50 mg), aqueous phosphate buffer (2.5 mL, 0.1 M, pH. 7.1), n-butanol (500 μl), and wet whole cells of Arthrobacter sp. lipase (100 mg) were shaken (320 rpm) continuously at 25 ± 1 C. After a certain degree of conversion (∼42%) as indicated by chiral high performance liquid chromatography (HPLC), the reaction was terminated by adding ethyl acetate and centrifuging the mixture at 10,000-15,000 g to remove the enzyme and the suspended particles. The clear solution was decanted and the centrifuged mass was extracted separately with ethyl acetate (3 × 25 mL). The organic layers were combined, washed with water, and treated with 2 M NaOH solution to give (S)-2,3-hydrobenzo[1,4]dioxane-2-carboxylic acid as its salt. The salt was neutralized with dilute HCl to give enantiomerically pure (S)-2,3-dihydrobenzo[1,4]dioxane-2-carboxylic acid (yield 42%). ee = 99%; mp = 102-103 C; [α]D25=-61.0 (c 1, CHCl3); Abs, config. (S); {lit.23b [α]25D=-63.8(c 1, CHCl3); ee = 99.0%; mp 97.5 C}; HPLC conditions {OJ-H chiral column, eluent 2-propanol-hexane-triflouroacetic acid (5:95:0.1), flow rate: 0.5 mL/min, t1 = 20.78 and t2 = 22.87 min}. The organic layer was dried and evaporated under reduced pressure to furnish the optically active unhydrolyzed ester. ee = 73%; mp = 58-61 C; [α]D25=+46.4(c 1, CHCl3) [lit.23b [α]D25=57.0 (c 1, CHCl3), mp 78.1]; Abs. config. (R); HPLC conditions {OJ-H chiral column, eluent 2-propanol-hexane-triflouroacetic acid (5:95:0.1), flow rate: 0.5 mL/min, t1 = 31.74 and t2 = 33.34 min}. The enantiomerically pure ester with ee = 99%; mp = 73-76 C; [α]25D=+55.4 (c 1, CHCl3); Abs. config. (R); {lit.23b [α]D25=+57.0 (c 1, CHCl3); ee = 99.4%; mp 78.5 C}, was obtained in the case of hydrolysis with diisopropylether as the co-solvent (Table 2, entry 13).

Reference： [1]Tetrahedron Asymmetry,2012,vol. 23,p. 1615 - 1623
[2]Tetrahedron Letters,2016,vol. 57,p. 2009 - 2011

15
[ 3663-79-4 ]
[ 70918-54-6 ]
[ 70918-53-5 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Racemic methyl 1,4-benzodioxan-2-carboxylate 17a (50 mg), aqueous phosphate buffer (2.5 mL, 0.1 M, pH. 7.1), n-butanol (500 μl), and wet whole cells of Arthrobacter sp. lipase (100 mg) were shaken (320 rpm) continuously at 25 ± 1 C. After a certain degree of conversion (∼42%) as indicated by chiral high performance liquid chromatography (HPLC), the reaction was terminated by adding ethyl acetate and centrifuging the mixture at 10,000-15,000 g to remove the enzyme and the suspended particles. The clear solution was decanted and the centrifuged mass was extracted separately with ethyl acetate (3 × 25 mL). The organic layers were combined, washed with water, and treated with 2 M NaOH solution to give (S)-2,3-hydrobenzo[1,4]dioxane-2-carboxylic acid as its salt. The salt was neutralized with dilute HCl to give enantiomerically pure (S)-2,3-dihydrobenzo[1,4]dioxane-2-carboxylic acid (yield 42%). ee = 99%; mp = 102-103 C; [α]D25=-61.0 (c 1, CHCl3); Abs, config. (S); {lit.23b [α]25D=-63.8(c 1, CHCl3); ee = 99.0%; mp 97.5 C}; HPLC conditions {OJ-H chiral column, eluent 2-propanol-hexane-triflouroacetic acid (5:95:0.1), flow rate: 0.5 mL/min, t1 = 20.78 and t2 = 22.87 min}. The organic layer was dried and evaporated under reduced pressure to furnish the optically active unhydrolyzed ester. ee = 73%; mp = 58-61 C; [α]D25=+46.4(c 1, CHCl3) [lit.23b [α]D25=57.0 (c 1, CHCl3), mp 78.1]; Abs. config. (R); HPLC conditions {OJ-H chiral column, eluent 2-propanol-hexane-triflouroacetic acid (5:95:0.1), flow rate: 0.5 mL/min, t1 = 31.74 and t2 = 33.34 min}. The enantiomerically pure ester with ee = 99%; mp = 73-76 C; [α]25D=+55.4 (c 1, CHCl3); Abs. config. (R); {lit.23b [α]D25=+57.0 (c 1, CHCl3); ee = 99.4%; mp 78.5 C}, was obtained in the case of hydrolysis with diisopropylether as the co-solvent (Table 2, entry 13).

Reference： [1]Tetrahedron Asymmetry,2012,vol. 23,p. 1615 - 1623

16
[ 3663-79-4 ]
(R)-(+)-1,4-benzodioxan-2-carboxylic acid sodium salt [ No CAS ]
(S)-(-)-1,4-benzodioxan-2-carboxylic acid sodium salt [ No CAS ]
(S)‐methyl 1,4‐benzodioxane‐2‐carboxylate [ No CAS ]
(R)-methyl 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71 % ee	With whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase In aq. phosphate buffer; di-isopropyl ether at 25℃; for 0.333333h; enantioselective reaction;	4.8 Lipase catalyzed hydrolysis of (±)-methyl 1,4-benzodioxan-2-carboxylate General procedure: Racemic methyl 1,4-benzodioxan-2-carboxylate 17a (50 mg), aqueous phosphate buffer (2.5 mL, 0.1 M, pH. 7.1), n-butanol (500 μl), and wet whole cells of Arthrobacter sp. lipase (100 mg) were shaken (320 rpm) continuously at 25 ± 1 °C. After a certain degree of conversion (∼42%) as indicated by chiral high performance liquid chromatography (HPLC), the reaction was terminated by adding ethyl acetate and centrifuging the mixture at 10,000-15,000 g to remove the enzyme and the suspended particles. The clear solution was decanted and the centrifuged mass was extracted separately with ethyl acetate (3 × 25 mL). The organic layers were combined, washed with water, and treated with 2 M NaOH solution to give (S)-2,3-hydrobenzo[1,4]dioxane-2-carboxylic acid as its salt. The salt was neutralized with dilute HCl to give enantiomerically pure (S)-2,3-dihydrobenzo[1,4]dioxane-2-carboxylic acid (yield 42%). ee = 99%; mp = 102-103 °C; [α]D25=-61.0 (c 1, CHCl3); Abs, config. (S); {lit.23b [α]25D=-63.8(c 1, CHCl3); ee = 99.0%; mp 97.5 °C}; HPLC conditions {OJ-H chiral column, eluent 2-propanol-hexane-triflouroacetic acid (5:95:0.1), flow rate: 0.5 mL/min, t1 = 20.78 and t2 = 22.87 min}. The organic layer was dried and evaporated under reduced pressure to furnish the optically active unhydrolyzed ester. ee = 73%; mp = 58-61 °C; [α]D25=+46.4(c 1, CHCl3) [lit.23b [α]D25=57.0 (c 1, CHCl3), mp 78.1]; Abs. config. (R); HPLC conditions {OJ-H chiral column, eluent 2-propanol-hexane-triflouroacetic acid (5:95:0.1), flow rate: 0.5 mL/min, t1 = 31.74 and t2 = 33.34 min}. The enantiomerically pure ester with ee = 99%; mp = 73-76 °C; [α]25D=+55.4 (c 1, CHCl3); Abs. config. (R); {lit.23b [α]D25=+57.0 (c 1, CHCl3); ee = 99.4%; mp 78.5 °C}, was obtained in the case of hydrolysis with diisopropylether as the co-solvent (Table 2, entry 13).

Reference： [1]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]

17
[ 3663-79-4 ]
(S)-(-)-1,4-benzodioxan-2-carboxylic acid sodium salt [ No CAS ]
(S)‐methyl 1,4‐benzodioxane‐2‐carboxylate [ No CAS ]
(R)-methyl 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73 % ee	With whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase In aq. phosphate buffer; butan-1-ol at 25℃; for 4h; enantioselective reaction;	4.8 Lipase catalyzed hydrolysis of (±)-methyl 1,4-benzodioxan-2-carboxylate General procedure: Racemic methyl 1,4-benzodioxan-2-carboxylate 17a (50 mg), aqueous phosphate buffer (2.5 mL, 0.1 M, pH. 7.1), n-butanol (500 μl), and wet whole cells of Arthrobacter sp. lipase (100 mg) were shaken (320 rpm) continuously at 25 ± 1 °C. After a certain degree of conversion (∼42%) as indicated by chiral high performance liquid chromatography (HPLC), the reaction was terminated by adding ethyl acetate and centrifuging the mixture at 10,000-15,000 g to remove the enzyme and the suspended particles. The clear solution was decanted and the centrifuged mass was extracted separately with ethyl acetate (3 × 25 mL). The organic layers were combined, washed with water, and treated with 2 M NaOH solution to give (S)-2,3-hydrobenzo[1,4]dioxane-2-carboxylic acid as its salt. The salt was neutralized with dilute HCl to give enantiomerically pure (S)-2,3-dihydrobenzo[1,4]dioxane-2-carboxylic acid (yield 42%). ee = 99%; mp = 102-103 °C; [α]D25=-61.0 (c 1, CHCl3); Abs, config. (S); {lit.23b [α]25D=-63.8(c 1, CHCl3); ee = 99.0%; mp 97.5 °C}; HPLC conditions {OJ-H chiral column, eluent 2-propanol-hexane-triflouroacetic acid (5:95:0.1), flow rate: 0.5 mL/min, t1 = 20.78 and t2 = 22.87 min}. The organic layer was dried and evaporated under reduced pressure to furnish the optically active unhydrolyzed ester. ee = 73%; mp = 58-61 °C; [α]D25=+46.4(c 1, CHCl3) [lit.23b [α]D25=57.0 (c 1, CHCl3), mp 78.1]; Abs. config. (R); HPLC conditions {OJ-H chiral column, eluent 2-propanol-hexane-triflouroacetic acid (5:95:0.1), flow rate: 0.5 mL/min, t1 = 31.74 and t2 = 33.34 min}. The enantiomerically pure ester with ee = 99%; mp = 73-76 °C; [α]25D=+55.4 (c 1, CHCl3); Abs. config. (R); {lit.23b [α]D25=+57.0 (c 1, CHCl3); ee = 99.4%; mp 78.5 °C}, was obtained in the case of hydrolysis with diisopropylether as the co-solvent (Table 2, entry 13).

Reference： [1]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]

18
[ 3663-79-4 ]
(R)-(+)-1,4-benzodioxan-2-carboxylic acid sodium salt [ No CAS ]
(S)-(-)-1,4-benzodioxan-2-carboxylic acid sodium salt [ No CAS ]
(R)-methyl 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99 % ee	With whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase In aq. phosphate buffer; di-isopropyl ether at 25℃; for 2h; enantioselective reaction;	4.8 Lipase catalyzed hydrolysis of (±)-methyl 1,4-benzodioxan-2-carboxylate General procedure: Racemic methyl 1,4-benzodioxan-2-carboxylate 17a (50 mg), aqueous phosphate buffer (2.5 mL, 0.1 M, pH. 7.1), n-butanol (500 μl), and wet whole cells of Arthrobacter sp. lipase (100 mg) were shaken (320 rpm) continuously at 25 ± 1 °C. After a certain degree of conversion (∼42%) as indicated by chiral high performance liquid chromatography (HPLC), the reaction was terminated by adding ethyl acetate and centrifuging the mixture at 10,000-15,000 g to remove the enzyme and the suspended particles. The clear solution was decanted and the centrifuged mass was extracted separately with ethyl acetate (3 × 25 mL). The organic layers were combined, washed with water, and treated with 2 M NaOH solution to give (S)-2,3-hydrobenzo[1,4]dioxane-2-carboxylic acid as its salt. The salt was neutralized with dilute HCl to give enantiomerically pure (S)-2,3-dihydrobenzo[1,4]dioxane-2-carboxylic acid (yield 42%). ee = 99%; mp = 102-103 °C; [α]D25=-61.0 (c 1, CHCl3); Abs, config. (S); {lit.23b [α]25D=-63.8(c 1, CHCl3); ee = 99.0%; mp 97.5 °C}; HPLC conditions {OJ-H chiral column, eluent 2-propanol-hexane-triflouroacetic acid (5:95:0.1), flow rate: 0.5 mL/min, t1 = 20.78 and t2 = 22.87 min}. The organic layer was dried and evaporated under reduced pressure to furnish the optically active unhydrolyzed ester. ee = 73%; mp = 58-61 °C; [α]D25=+46.4(c 1, CHCl3) [lit.23b [α]D25=57.0 (c 1, CHCl3), mp 78.1]; Abs. config. (R); HPLC conditions {OJ-H chiral column, eluent 2-propanol-hexane-triflouroacetic acid (5:95:0.1), flow rate: 0.5 mL/min, t1 = 31.74 and t2 = 33.34 min}. The enantiomerically pure ester with ee = 99%; mp = 73-76 °C; [α]25D=+55.4 (c 1, CHCl3); Abs. config. (R); {lit.23b [α]D25=+57.0 (c 1, CHCl3); ee = 99.4%; mp 78.5 °C}, was obtained in the case of hydrolysis with diisopropylether as the co-solvent (Table 2, entry 13).

Reference： [1]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]

19
[ 3663-79-4 ]
C₁₀H₉F₃O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 0.33 h / 25 °C / pH 7.1 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere 3: triethylamine / chloroform / 2 h / 0 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 2 h / 25 °C / pH 7.1 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere 3: triethylamine / chloroform / 2 h / 0 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; butan-1-ol / 4 h / 25 °C / pH 7.1 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere 3: triethylamine / chloroform / 2 h / 0 °C / Inert atmosphere

Reference： [1]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[2]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[3]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]

20
[ 3663-79-4 ]
C₁₀H₉F₃O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 2 h / 25 °C / pH 7.1 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere 3: triethylamine / chloroform / 2 h / 0 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; butan-1-ol / 4 h / 25 °C / pH 7.1 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere 3: triethylamine / chloroform / 2 h / 0 °C / Inert atmosphere

Reference： [1]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[2]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]

21
[ 3663-79-4 ]
[ 3663-80-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	With water; lithium hydroxide; In tetrahydrofuran; for 3h;	General procedure: Methyl 1,4-benzodioxan-2-carboxylate (±)-17a was dissolved in THF/ H2O (1:1 ratio) after which lithium hydroxide was added. The reaction was stirred for 3 h until hydrolysis was complete. Next, THF was evaporated and the residue acidified with 10percent HCl. DCM was used for extraction. The organic layers were dried in vacuo to give (±)-1,4-benzodioxan-2-carboxylic acid 1 in 91percent yield as a white solid; mp 117?119 °C; [lit.23b 125.4]; 1H NMR: delta 4.44 (d, J = 4.8 Hz, 2H), 4.90 (t, J = 3.7, 7.6 Hz, 1H), 6.88?6.97 (m, 3H), 6.99?7.02 (m, 1H); 13C NMR: delta 64.63, 71.61, 117.34, 122.38, 141.97, 142.87 173.59; HRMS (ESI) Calcd for C9H8NaO4 (M+Na): 203.0320. Found: 203.0317.
	With water; lithium hydroxide; In tetrahydrofuran; at 20℃; for 4h;	0.5 mol methyl1,4-benzodioxan-2-carboxylate, 0.75 mollithium hydroxide were added to 200 mL tetrahydrofuran and 200 mL H2O.The mixture was stirredat room temperature for 4 hours. Tetrahydrofuran was evaporated underreduced pressure, and then the residue acidified with diluted hydrochloric acidand extracted with dichloromethane. The organic layers washed with water, driedover anhydrous sodium sulfate, after evaporating to dryness under reducedpressure, to give 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylicacid.

Reference： [1]Tetrahedron Asymmetry,2012,vol. 23,p. 1615 - 1623
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 1766 - 1770

22
[ 3663-79-4 ]
[ 70918-53-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 0.33 h / 25 °C / pH 7.1 2: lithium hydroxide; water / tetrahydrofuran / 3 h
	Multi-step reaction with 2 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 2 h / 25 °C / pH 7.1 2: lithium hydroxide; water / tetrahydrofuran / 3 h
	Multi-step reaction with 2 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; butan-1-ol / 4 h / 25 °C / pH 7.1 2: lithium hydroxide; water / tetrahydrofuran / 3 h

	Multi-step reaction with 2 steps 1.1: magnesium chloride / tetrahydrofuran / 1 h / 20 °C / Resolution of racemate 1.2: 20 °C / Resolution of racemate 2.1: hydrogenchloride / 1,4-dioxane / 90 °C
	Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 12 h / Reflux; Irradiation 1.2: 3 h / 50 °C 2.1: lithium hydroxide monohydrate / methanol / 2 h / Reflux 3.1: hydrogen; bis(norbornadiene)rhodium(l)tetrafluoroborate; C₄₆H₃₈F₆FeN₂P₂S / dichloromethane / 12 h / 25 °C / 7600.51 Torr / Autoclave

Reference： [1]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[2]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[3]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[4]Fumagalli, Laura; Bolchi, Cristiano; Bavo, Francesco; Pallavicini, Marco [Tetrahedron Letters, 2016, vol. 57, # 18, p. 2009 - 2011]
[5]Yin, Xuguang; Huang, Yi; Chen, Ziyi; Hu, Yang; Tao, Lin; Zhao, Qingyang; Dong, Xiu-Qin; Zhang, Xumu [Organic Letters, 2018, vol. 20, # 14, p. 4173 - 4177]

23
[ 3663-79-4 ]
[ 98572-00-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 2 h / 25 °C / pH 7.1 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; butan-1-ol / 4 h / 25 °C / pH 7.1 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 12 h / Reflux; Irradiation 1.2: 3 h / 50 °C 2.1: hydrogen; bis(norbornadiene)rhodium(l)tetrafluoroborate; C₄₆H₃₈F₆FeN₂P₂S / dichloromethane / 12 h / 25 °C / 7600.51 Torr / Autoclave 3.1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -78 - 25 °C

Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 12 h / Reflux; Irradiation 1.2: 3 h / 50 °C 2.1: hydrogen; 1,2-bis((2S,5S)-2,5-dimethylphospholano)benzene; bis(norbornadiene)rhodium(l)tetrafluoroborate / methanol / 12 h / 25 °C / 22801.5 Torr / Autoclave 3.1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -78 - 25 °C

Reference： [1]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[2]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[3]Yin, Xuguang; Huang, Yi; Chen, Ziyi; Hu, Yang; Tao, Lin; Zhao, Qingyang; Dong, Xiu-Qin; Zhang, Xumu [Organic Letters, 2018, vol. 20, # 14, p. 4173 - 4177]
[4]Yin, Xuguang; Huang, Yi; Chen, Ziyi; Hu, Yang; Tao, Lin; Zhao, Qingyang; Dong, Xiu-Qin; Zhang, Xumu [Organic Letters, 2018, vol. 20, # 14, p. 4173 - 4177]

24
[ 3663-79-4 ]
[ 62501-72-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 2 h / 25 °C / pH 7.1 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; butan-1-ol / 4 h / 25 °C / pH 7.1 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere

Reference： [1]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[2]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]

25
[ 3663-79-4 ]
[ 60998-62-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 0.33 h / 25 °C / pH 7.1 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere 3: triethylamine / chloroform / 2 h / 0 °C / Inert atmosphere 4: chloroform / 6 h / Inert atmosphere
	Multi-step reaction with 4 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 2 h / 25 °C / pH 7.1 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere 3: triethylamine / chloroform / 2 h / 0 °C / Inert atmosphere 4: chloroform / 6 h / Inert atmosphere
	Multi-step reaction with 4 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; butan-1-ol / 4 h / 25 °C / pH 7.1 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere 3: triethylamine / chloroform / 2 h / 0 °C / Inert atmosphere 4: chloroform / 6 h / Inert atmosphere

Reference： [1]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[2]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[3]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]

26
[ 3663-79-4 ]
[ 61045-71-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 0.33 h / 25 °C / pH 7.1 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere 3: triethylamine / chloroform / 2 h / 0 °C / Inert atmosphere 4: chloroform / 8 h / Inert atmosphere
	Multi-step reaction with 4 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 2 h / 25 °C / pH 7.1 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere 3: triethylamine / chloroform / 2 h / 0 °C / Inert atmosphere 4: chloroform / 8 h / Inert atmosphere
	Multi-step reaction with 4 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; butan-1-ol / 4 h / 25 °C / pH 7.1 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere 3: triethylamine / chloroform / 2 h / 0 °C / Inert atmosphere 4: chloroform / 8 h / Inert atmosphere

Reference： [1]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[2]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[3]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]

27
[ 3663-79-4 ]
[ 61045-70-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 2 h / 25 °C / pH 7.1 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere 3: triethylamine / chloroform / 2 h / 0 °C / Inert atmosphere 4: chloroform / 8 h / Inert atmosphere
	Multi-step reaction with 4 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; butan-1-ol / 4 h / 25 °C / pH 7.1 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere 3: triethylamine / chloroform / 2 h / 0 °C / Inert atmosphere 4: chloroform / 8 h / Inert atmosphere

Reference： [1]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[2]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]

28
[ 3663-79-4 ]
[ 61120-80-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 0.33 h / 25 °C / pH 7.1 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere 3: triethylamine / chloroform / 2 h / 0 °C / Inert atmosphere 4: chloroform / 8 h / 60 °C / Inert atmosphere
	Multi-step reaction with 4 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 2 h / 25 °C / pH 7.1 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere 3: triethylamine / chloroform / 2 h / 0 °C / Inert atmosphere 4: chloroform / 8 h / 60 °C / Inert atmosphere
	Multi-step reaction with 4 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; butan-1-ol / 4 h / 25 °C / pH 7.1 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere 3: triethylamine / chloroform / 2 h / 0 °C / Inert atmosphere 4: chloroform / 8 h / 60 °C / Inert atmosphere

Reference： [1]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[2]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[3]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]

29
[ 3663-79-4 ]
[ 60998-61-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 2 h / 25 °C / pH 7.1 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere 3: triethylamine / chloroform / 2 h / 0 °C / Inert atmosphere 4: chloroform / 8 h / 60 °C / Inert atmosphere
	Multi-step reaction with 4 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; butan-1-ol / 4 h / 25 °C / pH 7.1 2: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere 3: triethylamine / chloroform / 2 h / 0 °C / Inert atmosphere 4: chloroform / 8 h / 60 °C / Inert atmosphere

Reference： [1]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[2]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]

30
[ 3663-79-4 ]
[ 1219800-50-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 2 h / 25 °C / pH 7.1 2: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran; dichloromethane / 0.17 h / 0 °C
	Multi-step reaction with 3 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 0.33 h / 25 °C / pH 7.1 2: lithium hydroxide; water / tetrahydrofuran / 3 h 3: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran; dichloromethane / 0.17 h / 0 °C
	Multi-step reaction with 3 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 2 h / 25 °C / pH 7.1 2: lithium hydroxide; water / tetrahydrofuran / 3 h 3: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran; dichloromethane / 0.17 h / 0 °C

	Multi-step reaction with 3 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; butan-1-ol / 4 h / 25 °C / pH 7.1 2: lithium hydroxide; water / tetrahydrofuran / 3 h 3: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran; dichloromethane / 0.17 h / 0 °C
	Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 12 h / Reflux; Irradiation 1.2: 3 h / 50 °C 2.1: lithium hydroxide monohydrate / methanol / 2 h / Reflux 3.1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux 4.1: triethylamine / dichloromethane / 2 h / 0 - 25 °C 5.1: hydrogen; bis(norbornadiene)rhodium(l)tetrafluoroborate; (S,R)-ZhaoPhos / dichloromethane / 12 h / 25 °C / 7600.51 Torr / Autoclave

Reference： [1]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[2]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[3]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[4]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[5]Yin, Xuguang; Huang, Yi; Chen, Ziyi; Hu, Yang; Tao, Lin; Zhao, Qingyang; Dong, Xiu-Qin; Zhang, Xumu [Organic Letters, 2018, vol. 20, # 14, p. 4173 - 4177]

31
[ 3663-79-4 ]
[ 860173-98-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 2 h / 25 °C / pH 7.1 2: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran; dichloromethane / 0.17 h / 0 °C 3: trifluoroacetic acid / dichloromethane / 1 h / 0 °C
	Multi-step reaction with 4 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 0.33 h / 25 °C / pH 7.1 2: lithium hydroxide; water / tetrahydrofuran / 3 h 3: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran; dichloromethane / 0.17 h / 0 °C 4: trifluoroacetic acid / dichloromethane / 1 h / 0 °C
	Multi-step reaction with 4 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; di-isopropyl ether / 2 h / 25 °C / pH 7.1 2: lithium hydroxide; water / tetrahydrofuran / 3 h 3: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran; dichloromethane / 0.17 h / 0 °C 4: trifluoroacetic acid / dichloromethane / 1 h / 0 °C

	Multi-step reaction with 4 steps 1: whole cells of Arthrobacter sp. ABL MTCC No_. 5125 lipase / aq. phosphate buffer; butan-1-ol / 4 h / 25 °C / pH 7.1 2: lithium hydroxide; water / tetrahydrofuran / 3 h 3: triethylamine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran; dichloromethane / 0.17 h / 0 °C 4: trifluoroacetic acid / dichloromethane / 1 h / 0 °C
	Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 12 h / Reflux; Irradiation 1.2: 3 h / 50 °C 2.1: lithium hydroxide monohydrate / methanol / 2 h / Reflux 3.1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux 4.1: triethylamine / dichloromethane / 2 h / 0 - 25 °C 5.1: hydrogen; bis(norbornadiene)rhodium(l)tetrafluoroborate; (S,R)-ZhaoPhos / dichloromethane / 12 h / 25 °C / 7600.51 Torr / Autoclave 6.1: trifluoroacetic acid / dichloromethane / 6 h / 0 - 20 °C

Reference： [1]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[2]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[3]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[4]Rouf, Abdul; Gupta, Pankaj; Aga, Mushtaq A.; Kumar, Brijesh; Chaubey, Asha; Parshad, Rajinder; Taneja, Subhash C. [Tetrahedron Asymmetry, 2012, vol. 23, # 22-23, p. 1615 - 1623]
[5]Yin, Xuguang; Huang, Yi; Chen, Ziyi; Hu, Yang; Tao, Lin; Zhao, Qingyang; Dong, Xiu-Qin; Zhang, Xumu [Organic Letters, 2018, vol. 20, # 14, p. 4173 - 4177]

32
[ 3663-79-4 ]
[ 3663-82-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate; titanium tetrachloride In 1,2-dimethoxyethane at 0 - 20℃;
	With lithium aluminium tetrahydride In tetrahydrofuran at 20℃;	General procedure for the preparation of (2-substituted 2,3-dihydro-benzo[b][1,4]dioxin-3-yl)methanol (6a-6c) General procedure: Asolution of 0.1 mol 1a-1c in 50 mLanhydrous tetrahydrofuran was added dropwise to an ice-water bath, stirredmixture of lithium aluminum hydride in 50 mL anhydrous tetrahydrofuran. The mixture was stirredat room-temperature for 8-16 hours. Then the reaction quenched by the additionof water with ice cooling. The mixture was extracted with ether, and then theextract were washed with water and dried, and evaporated. The crudeproducts was purified by column chromatography, eluting with ethyl acetate-petroleumether 1:1(v:v).

Reference： [1]Liu, Xin; Wang, Songlin; Chen, Yin; Liu, Xinghua; Xu, Xiangqing; Liu, Bi-Feng; Zhang, Guisen [Archiv der Pharmazie, 2014, vol. 347, # 1, p. 32 - 41]
[2]Wang, Songlin; Chen, Yin; Zhao, Song; Xu, Xiangqing; Liu, Xin; Liu, Bi-Feng; Zhang, Guisen [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 7, p. 1766 - 1770]

33
[ 3663-79-4 ]
[ 3886-69-9 ]
(S)-N-((R)-1-phenylethyl)-2,3-dihydrobenzo [b][1,4]dioxine-2-carboxamide [ No CAS ]
(R)-N-((R)-1-phenylethyl)-2,3-dihydrobenzo [b][1,4]dioxine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 94.8% 2: 80%	Stage #1: methyl 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylate With magnesium chloride In tetrahydrofuran at 20℃; for 1h; Resolution of racemate; Stage #2: (R)-1-phenyl-ethyl-amine In tetrahydrofuran at 20℃; Resolution of racemate;

Reference： [1]Fumagalli, Laura; Bolchi, Cristiano; Bavo, Francesco; Pallavicini, Marco [Tetrahedron Letters, 2016, vol. 57, # 18, p. 2009 - 2011]

34
[ 3663-79-4 ]
[ 46049-48-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: magnesium chloride / tetrahydrofuran / 1 h / 20 °C / Resolution of racemate 1.2: 20 °C / Resolution of racemate 2.1: toluene-4-sulfonic acid / toluene / 2 h / Reflux 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / Cooling; Reflux

Reference： [1]Fumagalli, Laura; Bolchi, Cristiano; Bavo, Francesco; Pallavicini, Marco [Tetrahedron Letters, 2016, vol. 57, # 18, p. 2009 - 2011]

35
[ 3663-79-4 ]
methyl benzo[b][1,4]dioxine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: methyl 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylate With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 12h; Reflux; Irradiation; Stage #2: With sodium iodide In acetone at 50℃; for 3h;

Reference： [1]Yin, Xuguang; Huang, Yi; Chen, Ziyi; Hu, Yang; Tao, Lin; Zhao, Qingyang; Dong, Xiu-Qin; Zhang, Xumu [Organic Letters, 2018, vol. 20, # 14, p. 4173 - 4177]

36
[ 3663-79-4 ]
[ 62501-70-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 12 h / Reflux; Irradiation 1.2: 3 h / 50 °C 2.1: hydrogen; bis(norbornadiene)rhodium(l)tetrafluoroborate; C₄₆H₃₈F₆FeN₂P₂S / dichloromethane / 12 h / 25 °C / 7600.51 Torr / Autoclave 3.1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -78 - 25 °C 4.1: triethylamine / dichloromethane / 0 - 25 °C
	Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 12 h / Reflux; Irradiation 1.2: 3 h / 50 °C 2.1: hydrogen; 1,2-bis((2S,5S)-2,5-dimethylphospholano)benzene; bis(norbornadiene)rhodium(l)tetrafluoroborate / methanol / 12 h / 25 °C / 22801.5 Torr / Autoclave 3.1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -78 - 25 °C 4.1: triethylamine / dichloromethane / 0 - 25 °C

Reference： [1]Yin, Xuguang; Huang, Yi; Chen, Ziyi; Hu, Yang; Tao, Lin; Zhao, Qingyang; Dong, Xiu-Qin; Zhang, Xumu [Organic Letters, 2018, vol. 20, # 14, p. 4173 - 4177]
[2]Yin, Xuguang; Huang, Yi; Chen, Ziyi; Hu, Yang; Tao, Lin; Zhao, Qingyang; Dong, Xiu-Qin; Zhang, Xumu [Organic Letters, 2018, vol. 20, # 14, p. 4173 - 4177]

37
[ 3663-79-4 ]
(-)-Doxazosin hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 12 h / Reflux; Irradiation 1.2: 3 h / 50 °C 2.1: lithium hydroxide monohydrate / methanol / 2 h / Reflux 3.1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux 4.1: triethylamine / dichloromethane / 2 h / 0 - 25 °C 5.1: hydrogen; bis(norbornadiene)rhodium(l)tetrafluoroborate; (S,R)-ZhaoPhos / dichloromethane / 12 h / 25 °C / 7600.51 Torr / Autoclave 6.1: trifluoroacetic acid / dichloromethane / 6 h / 0 - 20 °C 7.1: butan-1-ol / 5 h / Reflux

Reference： [1]Yin, Xuguang; Huang, Yi; Chen, Ziyi; Hu, Yang; Tao, Lin; Zhao, Qingyang; Dong, Xiu-Qin; Zhang, Xumu [Organic Letters, 2018, vol. 20, # 14, p. 4173 - 4177]

38
[ 3663-79-4 ]
(S)‐methyl 1,4‐benzodioxane‐2‐carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 12 h / Reflux; Irradiation 1.2: 3 h / 50 °C 2.1: hydrogen; 1,2-bis((2S,5S)-2,5-dimethylphospholano)benzene; bis(norbornadiene)rhodium(l)tetrafluoroborate / methanol / 12 h / 25 °C / 22801.5 Torr / Autoclave

Reference： [1]Yin, Xuguang; Huang, Yi; Chen, Ziyi; Hu, Yang; Tao, Lin; Zhao, Qingyang; Dong, Xiu-Qin; Zhang, Xumu [Organic Letters, 2018, vol. 20, # 14, p. 4173 - 4177]

39
[ 3663-79-4 ]
[ 67471-01-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 12 h / Reflux; Irradiation 1.2: 3 h / 50 °C 2.1: lithium hydroxide monohydrate / methanol / 2 h / Reflux

Reference： [1]Yin, Xuguang; Huang, Yi; Chen, Ziyi; Hu, Yang; Tao, Lin; Zhao, Qingyang; Dong, Xiu-Qin; Zhang, Xumu [Organic Letters, 2018, vol. 20, # 14, p. 4173 - 4177]

40
[ 3663-79-4 ]
benzo[b][1,4]dioxine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 12 h / Reflux; Irradiation 1.2: 3 h / 50 °C 2.1: lithium hydroxide monohydrate / methanol / 2 h / Reflux 3.1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux 4.1: ammonium hydroxide; triethylamine / dichloromethane / 2 h / 0 - 25 °C

Reference： [1]Yin, Xuguang; Huang, Yi; Chen, Ziyi; Hu, Yang; Tao, Lin; Zhao, Qingyang; Dong, Xiu-Qin; Zhang, Xumu [Organic Letters, 2018, vol. 20, # 14, p. 4173 - 4177]

41
[ 3663-79-4 ]
tert-butyl 4-(benzo[b][1,4]dioxine-2-carbonyl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 12 h / Reflux; Irradiation 1.2: 3 h / 50 °C 2.1: lithium hydroxide monohydrate / methanol / 2 h / Reflux 3.1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux 4.1: triethylamine / dichloromethane / 2 h / 0 - 25 °C

Reference： [1]Yin, Xuguang; Huang, Yi; Chen, Ziyi; Hu, Yang; Tao, Lin; Zhao, Qingyang; Dong, Xiu-Qin; Zhang, Xumu [Organic Letters, 2018, vol. 20, # 14, p. 4173 - 4177]

42
[ 3663-79-4 ]
N-(2-hydroxyethyl)benzo[b][1,4]dioxine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 12 h / Reflux; Irradiation 1.2: 3 h / 50 °C 2.1: lithium hydroxide monohydrate / methanol / 2 h / Reflux 3.1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux 4.1: triethylamine / dichloromethane / 2 h / 0 - 25 °C

Reference： [1]Yin, Xuguang; Huang, Yi; Chen, Ziyi; Hu, Yang; Tao, Lin; Zhao, Qingyang; Dong, Xiu-Qin; Zhang, Xumu [Organic Letters, 2018, vol. 20, # 14, p. 4173 - 4177]

43
[ 3663-79-4 ]
N-(3-hydroxypropyl)benzo[b][1,4]dioxine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 12 h / Reflux; Irradiation 1.2: 3 h / 50 °C 2.1: lithium hydroxide monohydrate / methanol / 2 h / Reflux 3.1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux 4.1: triethylamine / dichloromethane / 2 h / 0 - 25 °C

Reference： [1]Yin, Xuguang; Huang, Yi; Chen, Ziyi; Hu, Yang; Tao, Lin; Zhao, Qingyang; Dong, Xiu-Qin; Zhang, Xumu [Organic Letters, 2018, vol. 20, # 14, p. 4173 - 4177]

44
[ 3663-79-4 ]
(R)-methyl 2,3-dihydrobenzo[b][1,4]dioxine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 12 h / Reflux; Irradiation 1.2: 3 h / 50 °C 2.1: hydrogen; bis(norbornadiene)rhodium(l)tetrafluoroborate; C₄₆H₃₈F₆FeN₂P₂S / dichloromethane / 12 h / 25 °C / 7600.51 Torr / Autoclave
	Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 12 h / Reflux; Irradiation 1.2: 3 h / 50 °C 2.1: hydrogen; 1,2-bis((2S,5S)-2,5-dimethylphospholano)benzene; bis(norbornadiene)rhodium(l)tetrafluoroborate / methanol / 12 h / 25 °C / 22801.5 Torr / Autoclave

Reference： [1]Yin, Xuguang; Huang, Yi; Chen, Ziyi; Hu, Yang; Tao, Lin; Zhao, Qingyang; Dong, Xiu-Qin; Zhang, Xumu [Organic Letters, 2018, vol. 20, # 14, p. 4173 - 4177]
[2]Yin, Xuguang; Huang, Yi; Chen, Ziyi; Hu, Yang; Tao, Lin; Zhao, Qingyang; Dong, Xiu-Qin; Zhang, Xumu [Organic Letters, 2018, vol. 20, # 14, p. 4173 - 4177]

45
[ 3663-79-4 ]
[ 1616377-79-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 12 h / Reflux; Irradiation 1.2: 3 h / 50 °C 2.1: lithium hydroxide monohydrate / methanol / 2 h / Reflux 3.1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux 4.1: ammonium hydroxide; triethylamine / dichloromethane / 2 h / 0 - 25 °C 5.1: hydrogen; bis(norbornadiene)rhodium(l)tetrafluoroborate; C₄₆H₃₈F₆FeN₂P₂S / dichloromethane / 12 h / 25 °C / 7600.51 Torr / Autoclave

Reference： [1]Yin, Xuguang; Huang, Yi; Chen, Ziyi; Hu, Yang; Tao, Lin; Zhao, Qingyang; Dong, Xiu-Qin; Zhang, Xumu [Organic Letters, 2018, vol. 20, # 14, p. 4173 - 4177]

46
[ 3663-79-4 ]
(+)-N-(2-hydroxyethyl)-2,3-dihydrobenzo[b][1,4]dioxine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 12 h / Reflux; Irradiation 1.2: 3 h / 50 °C 2.1: lithium hydroxide monohydrate / methanol / 2 h / Reflux 3.1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux 4.1: triethylamine / dichloromethane / 2 h / 0 - 25 °C 5.1: hydrogen; bis(norbornadiene)rhodium(l)tetrafluoroborate; C₄₆H₃₈F₆FeN₂P₂S / dichloromethane / 12 h / 25 °C / 7600.51 Torr / Autoclave

Reference： [1]Yin, Xuguang; Huang, Yi; Chen, Ziyi; Hu, Yang; Tao, Lin; Zhao, Qingyang; Dong, Xiu-Qin; Zhang, Xumu [Organic Letters, 2018, vol. 20, # 14, p. 4173 - 4177]

47
[ 3663-79-4 ]
(+)-N-(3-hydroxypropyl)-2,3-dihydrobenzo[b][1,4]dioxine-2-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 12 h / Reflux; Irradiation 1.2: 3 h / 50 °C 2.1: lithium hydroxide monohydrate / methanol / 2 h / Reflux 3.1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux 4.1: triethylamine / dichloromethane / 2 h / 0 - 25 °C 5.1: hydrogen; bis(norbornadiene)rhodium(l)tetrafluoroborate; C₄₆H₃₈F₆FeN₂P₂S / dichloromethane / 12 h / 25 °C / 7600.51 Torr / Autoclave

Reference： [1]Yin, Xuguang; Huang, Yi; Chen, Ziyi; Hu, Yang; Tao, Lin; Zhao, Qingyang; Dong, Xiu-Qin; Zhang, Xumu [Organic Letters, 2018, vol. 20, # 14, p. 4173 - 4177]

48
[ 3663-79-4 ]
7-acetyl-1,4-benzodioxin-2-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 12 h / Reflux; Irradiation 1.2: 3 h / 50 °C 2.1: N,N-dimethyl acetamide; aluminum (III) chloride / dichloromethane / 12 h / 0 - 20 °C

Reference： [1]Yin, Xuguang; Huang, Yi; Chen, Ziyi; Hu, Yang; Tao, Lin; Zhao, Qingyang; Dong, Xiu-Qin; Zhang, Xumu [Organic Letters, 2018, vol. 20, # 14, p. 4173 - 4177]

49
[ 3663-79-4 ]
[ 77948-59-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 12 h / Reflux; Irradiation 1.2: 3 h / 50 °C 2.1: lithium hydroxide monohydrate / methanol / 2 h / Reflux 3.1: thionyl chloride / dichloromethane / 3 h / 0 °C / Reflux

Reference： [1]Yin, Xuguang; Huang, Yi; Chen, Ziyi; Hu, Yang; Tao, Lin; Zhao, Qingyang; Dong, Xiu-Qin; Zhang, Xumu [Organic Letters, 2018, vol. 20, # 14, p. 4173 - 4177]

50
[ 3663-79-4 ]
(E)-N'-(2,3,4-trihydroxybenzylidene)-2,3-dihydrobenzo[b][1,4] dioxine-2-carbohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: hydrazine hydrate / methanol / Reflux; Inert atmosphere 2: methanol / 12 h / 20 °C / Inert atmosphere

Reference： [1]Chen, Lixia; Gao, Suyu; Li, Hua; Li, Mingxue; Li, Xingzhou; Liu, Yang; Wu, Canrong; Yang, Kaiyin; Zhang, Yujie; Zheng, Mengzhu [Bioorganic Chemistry, 2020, vol. 96]

51
[ 3663-79-4 ]
[ 90557-92-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrate In methanol Reflux; Inert atmosphere;	2.1.1. General procedure for the synthesis of hydrazides 2 General procedure: Hydrazine hydrate (5 mL, 40%) was added to a solution of requiredester (5.0 mmol) in methanol (20 mL). The solution was refluxed for12-24 h and monitored by TLC until starting material was completelyconsumed. After that, solvent was evaporated under reduced pressureand a small amount of water (5 mL) was added to precipitate the hydrazide,which was filtered and dried in vacuum to give a shiny white toyellow solid in excellent yields, without further purification.

Reference： [1]Chen, Lixia; Gao, Suyu; Li, Hua; Li, Mingxue; Li, Xingzhou; Liu, Yang; Wu, Canrong; Yang, Kaiyin; Zhang, Yujie; Zheng, Mengzhu [Bioorganic Chemistry, 2020, vol. 96]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	3663-79-4	MDL No. :	MFCD00297092
Formula :	C₁₀H₁₀O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SNLAAGHHNZECPE-UHFFFAOYSA-N
M.W :	194.18	Pubchem ID :	3096253
Synonyms :

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	48.21
TPSA :	44.76 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.26 cm/s

Log Po/w (iLOGP) :	2.19
Log Po/w (XLOGP3) :	1.73
Log Po/w (WLOGP) :	1.0
Log Po/w (MLOGP) :	0.7
Log Po/w (SILICOS-IT) :	1.55
Consensus Log Po/w :	1.43

[ CAS No. 3663-79-4 ] {[proInfo.proName]}

Quality Control of [ 3663-79-4 ]

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Product Details of [ 3663-79-4 ]

Calculated chemistry of [ 3663-79-4 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 3663-79-4 ]

Application In Synthesis of [ 3663-79-4 ]

[ 3663-79-4 ] Synthesis Path-Upstream 1~1

[ 3663-79-4 ] Synthesis Path-Downstream 1~51

Related Functional Groups of
[ 3663-79-4 ]

Esters

Related Parent Nucleus of
[ 3663-79-4 ]

Benzodioxans

Precautionary Statements-General

Prevention

Response

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Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-2.32
Solubility :	0.932 mg/ml ; 0.0048 mol/l
Class :	Soluble
Log S (Ali) :	-2.29
Solubility :	1.0 mg/ml ; 0.00517 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.28
Solubility :	1.02 mg/ml ; 0.00526 mol/l
Class :	Soluble

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.81

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 3663-79-4 ] {[proInfo.proName]}

Quality Control of [ 3663-79-4 ]

Related Doc. of [ 3663-79-4 ]

Product Details of [ 3663-79-4 ]

Calculated chemistry of [ 3663-79-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 3663-79-4 ]

Application In Synthesis of [ 3663-79-4 ]

[ 3663-79-4 ] Synthesis Path-Upstream 1~1

[ 3663-79-4 ] Synthesis Path-Downstream 1~51

Related Functional Groups of [ 3663-79-4 ]

Esters

Related Parent Nucleus of [ 3663-79-4 ]

Benzodioxans

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 3663-79-4 ]

Related Parent Nucleus of
[ 3663-79-4 ]