[ CAS No. 10288-36-5 ] {[proInfo.proName]}

Name: 10288-36-5|2,3-Dihydrobenzo[b][1,4]dioxin-5-ol|97%
Brand: Ambeed
SKU: A104058
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Quality Control of [ 10288-36-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 10288-36-5 ]

Product Details of [ 10288-36-5 ]

CAS No. :	10288-36-5	MDL No. :	MFCD02103729
Formula :	C₈H₈O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IGXSSRPZRAIXQF-UHFFFAOYSA-N
M.W :	152.15	Pubchem ID :	82520
Synonyms :

Calculated chemistry of [ 10288-36-5 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	0
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	39.34
TPSA :	38.69 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.57
Log Po/w (XLOGP3) :	1.28
Log Po/w (WLOGP) :	1.16
Log Po/w (MLOGP) :	0.47
Log Po/w (SILICOS-IT) :	1.7
Consensus Log Po/w :	1.24

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.99
Solubility :	1.54 mg/ml ; 0.0102 mol/l
Class :	Very soluble
Log S (Ali) :	-1.69
Solubility :	3.09 mg/ml ; 0.0203 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.84
Solubility :	2.21 mg/ml ; 0.0146 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.31

Safety of [ 10288-36-5 ]

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

Application In Synthesis of [ 10288-36-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 10288-36-5 ]
Downstream synthetic route of [ 10288-36-5 ]

[ 10288-36-5 ] Synthesis Path-Upstream 1~3

1
[ 106-93-4 ]
[ 87-66-1 ]
[ 10288-36-5 ]

Reference： [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 11, p. 4693 - 4713
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 15, p. 3823 - 3842
[3] Patent: US6337336, 2002, B1, . Location in patent: Page column 5
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 511 - 520
[5] Chemische Berichte, 1879, vol. 12, p. 1860
[6] Journal of the American Chemical Society, 1959, vol. 81, p. 5199
[7] Journal of the Chemical Society, 1937, p. 49,52
[8] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 3, p. 307 - 310
[9] Patent: US2005/176726, 2005, A1, . Location in patent: Page/Page column 22

2
[ 154582-36-2 ]
[ 10288-36-5 ]

Reference： [1] Tetrahedron Letters, 1993, vol. 34, # 47, p. 7567 - 7568

3
[ 1710-55-0 ]
[ 10288-36-5 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 193 - 197

[ 10288-36-5 ] Synthesis Path-Downstream 1~79

1
[ 107-94-8 ]
[ 10288-36-5 ]
[ 412339-10-7 ]

Reference： [1]Journal of the Chemical Society,1937,p. 49,52

3
[ 106-93-4 ]
[ 87-66-1 ]
[ 10288-36-5 ]

Yield	Reaction Conditions	Operation in experiment
56%	With potassium carbonate; at 90℃; for 16h;	To a stirred solution of compound 1 (30g, 238mmol, 1 eq) in 2- butanolne (500ml_), was added K2CO3 (98g, 714mmol, 3eq) and (137g, 714mmol, 3eq). The resulted reaction mixture was heated dibromo ethane at 90 C for 16h. The reaction was monitored with TLC. TLC analysis indicated formation of a non-polar spot. The reaction mixture was poured into ice water and extracted with ethyl acetate. The combined organic layer was dried over Na2S04 and concentrated under reduced pressure. The crude product was purified by column chromatography (silica 100-200) using 0-30% ethyl acetate in petroleum ether as an eluent to give Compound 2 (20g, 56% yield) as a yellow oil. LCMS: m/z 153.32 (M+H):
	With potassium carbonate; In butanone; for 18.5h;Heating / reflux;	A mixture of benzene-1,2,3-triol (4.39 g, 34.81 mmol, Aldrich), 1,2-dibromoethane (1 mL, 11.6 mmol, Aldrich) and potassium carbonate (1.60 g, 11.58 mmol, Aldrich) in 2-butanone (300 mL, Aldrich) was heated to reflux for 18.5 h with stirring in an oil-bath. The reaction mixture was cooled to room temperature and diluted with DCM (100 mL) and water (50 mL). The DCM layer was separated, washed with 10% aqueous Na2S2O3 (50 mL) and brine (100 mL), dried over anhydrous sodium sulfate, filtered, and evaporated. The residue was purified by silica gel column chromatography (gradient: 0-5% MeOH/DCM) to give the title compound as an amorphous solid. MS (ESI, pos. ion.) m/z: 153 (M+1).

Reference： [1]Patent: WO2019/153080,2019,A1 .Location in patent: Paragraph 00308
[2]Journal of Medicinal Chemistry,2017,vol. 60,p. 4693 - 4713
[3]Journal of Medicinal Chemistry,2004,vol. 47,p. 3823 - 3842
[4]Patent: US6337336,2002,B1 .Location in patent: Page column 5
[5]Journal of the Chemical Society. Perkin transactions I,1988,p. 511 - 520
[6]Chemische Berichte,1879,vol. 12,p. 1860
[7]Journal of the American Chemical Society,1959,vol. 81,p. 5199
[8]Journal of the Chemical Society,1937,p. 49,52
[9]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 307 - 310
[10]Patent: US2005/176726,2005,A1 .Location in patent: Page/Page column 22

4
[ 3055-08-1 ]
[ 10288-36-5 ]
5-((2S,3R)-3-Methyl-oxiranylmethoxy)-2,3-dihydro-benzo[1,4]dioxine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 1364 - 1368

5
[ 1710-55-0 ]
[ 10288-36-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 193 - 197

6
[ 10288-36-5 ]
[ 6742-26-3 ]
[ 73763-71-0 ]

Reference： [1]Bulletin des Societes Chimiques Belges,1980,vol. 89,p. 57 - 66

7
[ 10288-36-5 ]
[ 106-95-6 ]
[ 10594-24-8 ]

Reference： [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 193 - 197

8
[ 10288-36-5 ]
[ 590-17-0 ]
[ 154582-36-2 ]

Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 7567 - 7568

9
[ 10288-36-5 ]
[ 42965-39-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 511 - 520

10
[ 154582-36-2 ]
[ 10288-36-5 ]

Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 7567 - 7568

11
[ 110-52-1 ]
[ 10288-36-5 ]
[ 22921-73-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 105 - 114

12
[ 10288-36-5 ]
[ 106-93-4 ]
[ 1710-62-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 105 - 114

13
[ 10288-36-5 ]
[ 109-64-8 ]
[ 3185-35-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 105 - 114

Yield	Reaction Conditions	Operation in experiment
		Step A 5-(2-Bromoethoxy)-2,3-dihydro-1,4-benzodioxin Dry potassium carbonate (10 eq.) is added to a solution in toluene (100 ml) of the phenolic compound obtained in Preparation 6 (2 g).

15
[ 10288-36-5 ]
[ 107-07-3 ]
[ 10288-38-7 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 3823 - 3842
[2]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 307 - 310

16
[ 10288-36-5 ]
[ 350-46-9 ]
5-(4-nitro-phenoxy)-2,3-dihydro-benzo[1,4]dioxine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 1023 - 1026

17
[ 10288-36-5 ]
[ 32604-73-2 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 3823 - 3842
[2]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 105 - 114

18
[ 10288-36-5 ]
[ 245762-30-5 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 3823 - 3842

19
[ 10288-36-5 ]
[2-(2,3-dihydrobenzo[1,4]dioxin-5-yloxy)ethyl]-[2-(1H-indol-3-yl)ethyl]amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 3823 - 3842

20
[ 10288-36-5 ]
[2-(2,3-Dihydro-benzo[1,4]dioxin-5-yloxy)-ethyl]-[3-(5-fluoro-1H-indol-3-yl)-propyl]-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 3823 - 3842

21
[ 10288-36-5 ]
4-(2,3-dihydro-benzo[1,4]dioxin-5-yloxy)-phenylamine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 1023 - 1026

22
[ 10288-36-5 ]
N-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yloxy)-phenyl]-butyramide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 1023 - 1026

23
[ 10288-36-5 ]
3-{1-[2-(2,3-dihydro-benzo[1,4]dioxin-5-yloxy)-ethyl]-1,2,3,6-tetrahydro-pyridin-4-yl}-1H-indole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 307 - 310

24
[ 10288-36-5 ]
3-{1-[2-(2,3-dihydro-benzo[1,4]dioxin-5-yloxy)ethyl]-1,2,3,6-tetrahydro-pyridin-4-yl}-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 307 - 310

25
[ 10288-36-5 ]
3-{1-[2-(2,3-dihydro-benzo[1,4]dioxin-5-yloxy)-ethyl]-piperidin-4-yl}-6-fluoro-1H-indole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 307 - 310

26
[ 10288-36-5 ]
3-{1-[2-(2,3-dihydro-benzo[1,4]dioxin-5-yloxy)-ethyl]-1,2,3,6-tetrahydro-pyridin-4-yl}-6-fluoro-1H-indole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 307 - 310

27
[ 10288-36-5 ]
3-{1-[2-(2,3-dihydro-benzo[1,4]dioxin-5-yloxy)-ethyl]-1,2,3,6-tetrahydro-pyridin-4-yl}-5-fluoro-1H-indole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 307 - 310

28
[ 10288-36-5 ]
5-Fluoro-3-{1-[2-(2,3-dihydrobenzo[1,4]dioxin-5-yloxy)ethyl]-piperidin-4-ylmethyl}-1 H-indole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 307 - 310

29
[ 10288-36-5 ]
[ 214895-06-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 105 - 114

30
[ 10288-36-5 ]
[ 261633-73-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 105 - 114

31
[ 10288-36-5 ]
N-[2-(2,3-dihydro-benzo[1,4]dioxin-5-yloxy)-ethyl]-acetamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 105 - 114

32
[ 10288-36-5 ]
N-[3-(2,3-Dihydro-1,4-benzodioxin-5-yloxy)propyl]acetamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 105 - 114

33
[ 10288-36-5 ]
N-[4(2,3-Dihydro-1,4-benzodioxin-5-yloxy)butyl]acetamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 105 - 114

34
[ 10288-36-5 ]
[ 214894-96-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 105 - 114

35
[ 10288-36-5 ]
[ 214895-05-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 105 - 114

36
[ 10288-36-5 ]
[ 214895-04-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 105 - 114

37
[ 10288-36-5 ]
[ 78953-65-8 ]

Reference： [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 1364 - 1368

38
[ 10288-36-5 ]
[ 117358-03-9 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 511 - 520

39
[ 10288-36-5 ]
[ 117358-04-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 511 - 520

40
[ 10288-36-5 ]
[ 117358-05-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 511 - 520

41
[ 10288-36-5 ]
[ 10288-86-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 193 - 197

42
[ 10288-36-5 ]
[ 123373-34-2 ]

Reference： [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 193 - 197

43
[ 10288-36-5 ]
[ 123373-35-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 193 - 197

44
[ 10288-36-5 ]
[ 123373-38-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 193 - 197

45
[ 10288-36-5 ]
[ 53324-43-9 ]

Reference： [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 193 - 197

46
[ 10288-36-5 ]
[ 123373-36-4 ]

Reference： [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 193 - 197

47
[ 10288-36-5 ]
[ 123373-37-5 ]

Reference： [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 193 - 197

48
[ 10288-36-5 ]
[ 68941-02-6 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 42 7,8-Ethylenedioxy-4-chromanone Using the procedure outlined in Example 37 but replacing 2,3-methylenedioxyphenol with 2,3-ethylenedioxyphenol provided the desired material.

Reference： [1]Journal of the Chemical Society,1937,p. 49,52
[2]Patent: US5089519,1992,A

49
[ 10288-36-5 ]
2,3,6,7,10,11-hexahydro-1,4,5,9,12-pentaoxa-benz[5,6]indeno[1,2-a]phenanthrene [ No CAS ]

Reference： [1]Journal of the Chemical Society,1937,p. 49,52

50
[ 10288-36-5 ]
8-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-2,3,8,9-tetrahydro-[1,4]dioxino[2,3-h]chromen-7-one [ No CAS ]

Reference： [1]Journal of the Chemical Society,1937,p. 49,52

51
[ 10288-36-5 ]
8-((E?)-2,3-dihydro-benzo[1,4]dioxin-6-ylmethylene)-2,3,8,9-tetrahydro-[1,4]dioxino[2,3-h]chromen-7-one [ No CAS ]

Reference： [1]Journal of the Chemical Society,1937,p. 49,52

52
[ 10288-36-5 ]
[ 107-07-3 ]
5-(2-chloroethoxy)-(2,3)-dihydrobenzo[1,4]dioxane [ No CAS ]

Reference： [1]Patent: US6337336,2002,B1 .Location in patent: Page column 6

Yield	Reaction Conditions	Operation in experiment
		PREPARATION 3 2,3-Ethylenedioxyphenol (Compound of Formula (IV) where n=2) A suspension of pyrogallol (126 g) and potassium carbonate (138 g) in dimethylformamide (500 mL) was stirred at 80 C. for 2 hours. 1,2-Dibromoethane (188 g) was then added dropwise over a 4 hour period and the resulting mixture was stirred at 80 C. overnight. Upon cooling, the mixture was filtered, and the filtrate was evaporated, dissolved in water (200 mL) and acidified with concentrated hydrochloric acid. The resulting mixture was extracted with toluene. The orgainc extract was washed with water, dried over sodium sulfate, filtered and evaporated. Fractional distillation (82 C., 0.05 mm) afforded 54.7 g of 2,6-ethylenedioxyphenol, as an oil.

54
[ 10288-36-5 ]
[ 4341-76-8 ]
[ 1191997-20-2 ]

Yield	Reaction Conditions	Operation in experiment
43%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 130℃; for 2h;	Example 33 (S)-3-Cyclohexyl-2-[4-(2,3-dihydro-benzo[1,4]dioxin-5-yloxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-propionamide To a stirred mixture of <strong>[10288-36-5]2,3-dihydro-1,4-benzodioxin-5-ol</strong> (1.00 g, 6.58 mmol) and ethyl-2-butynoate (1.48 g, 13.16 mmol) in tetrahydrofuran (10 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (1.00 g, 6.58 mmol). After addition was complete the mixture was stirred at 130 C. for 2 h. Upon completion of the reaction the tetrahydrofuran was removed in vacuo and the residue redissolved in dichloromethane and washed with 2N aqueous hydrochloric acid, 5% aqueous sodium hydroxide solution, a saturated sodium chloride solution and dried over magnesium sulfate. The crude product obtained was purified by ISCO flash chromatography (Teledyne Isco RediSep Flash Column 40 g; 0% to 50% ethyl acetate/hexanes) to afford, 3-(2,3-dihydro-benzo[1,4]dioxin-5-yloxy)-but-2-enoic acid ethyl ester (750 mg, 43%) as a colorless oil: LR-ES-MS m/z calculated for C14H16O5 [M]+ 264, observed [M+H]+ 265.

Reference： [1]Patent: US2009/264445,2009,A1 .Location in patent: Page/Page column 40

55
[ 13636-02-7 ]
[ 10288-36-5 ]
[ 1202707-41-2 ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at -5 - 20℃; for 24h;	Example 8: Preparation of N,N-dimethyl-3-[(benzo[1,4]dioxan-5-yl-oxy)-3-(thiophen-2-yl)-propylamine] oxalate (compound I8) [Show Image] 3-Dimethylamino-1-(thiophen-2-yl)-1-propanol (1.85g, 0.01 mol), 5-hydroxyl-benzo[1,4]dioxane (1.52g, 0.01mol) and triphenylphosphine (3.93g, 0.015mol) were dissolved in 80 mL anhydrous tetrahydrofuran. The mixture was slowly added dropwise with the solution of diethyl azodicarboxylate (2.61 g, 0.015mol) in 20 mL anhydrous tetrahydrofuran, and the reaction temperature was controlled by an ice-salt bath to be below -5C. After compeletion of the addition, the ice-salt bath was removed, and the reaction was performed at room temperature for 24h. After the reaction, tetrahydrofuran was distilled out under a reduced pressure, and the obtained oil liquid was dissolved in 100 mL ethyl acetate. The mixture was washed with diluted sodium hydroxide aqueous solution and saturated sodium chloride aqueous solution respectively, dried over anhydrous sodium sulfate, and separated by silica gel column chromatography to obtain 1.56g of N,N-dimethyl-3-[(benzo[1,4]dioxan- 5-yl-oxy)-3-(thiophen-2-yl)-propylamine] as a yellow oil. The yellow oil was dissolved in 50 mL ethyl acetate, the mixture was added with 0.41g (0.045mol) oxalic acid to generate a pale yellow precipitate, heated to reflux, cooled to room temperature, frozen for 2h, and filtrated under vacumm. The filter cake was washed with cold ethyl acetate to obtain 1.69g of the target compound as a pale yellow powdery solid in a yield of 39.1% and a melting point of 89-92C. MS (m/e): 320.5 (M+1+). 1H-NMR delta (ppm, CDCl3-d3): 7.22-7.24(dd,1H,5'-H); 6.99-7.00 (d,1H,3'-H); 6.92-6.94(dd,1H,4'-H); 6.61-6.65(t,1H,7-H); 6.49-6.51(d, 2H,6,8-H); 5.48-5.51(t,1H, CHO); 4.23-4.31 (t,4H,2,3-H); 2.44-2.47(t,2H,CH2N); 2.35-2.42(m,1H,CH2CH2N); 2.25(s,6H,N(CH3)2); 2.08-2.13(m,1H, CH2CH2N).

Reference： [1]Patent: EP2305669,2011,A1 .Location in patent: Page/Page column 12-13

56
[ 10288-36-5 ]
[ 653573-72-9 ]
[ 1202707-49-0 ]

Yield	Reaction Conditions	Operation in experiment
		Example 10: Preparation of N,N-dimethyl-3-[(benzo[1,4]dioxan-5-yl-oxy)-3-(furan-2-yl)propylamine] oxalate (compound I10) [Show Image] 3-Dimethylamino-1-(furan-2-yl)-1-propanol (1.69g, 0.01mol), 5-benzo[1,4]dioxane (1.52g, 0.01mol) and triphenylphosphine (3.93g, 0.015mol) was dissolved in 80 mL anhydrous tetrahydrofuran. The mixture was slowly added dropwise with the solution of diethyl azodicarboxylate (2.61g, 0.015mol) in 20 mL anhydrous tetrahydrofuran, and the reaction temperature was controlled by an ice-salt bath to be below -5C. After compeletion of the addition, the ice-salt bath was removed, and the reaction was performed at room temperature for 24h. After the reaction, tetrahydrofuran was distilled out under a reduced pressure, and the obtained oily liquid was dissolved in 100 mL ethyl acetate. The mixture was washed with diluted sodium hydroxide aqueous solution and saturated sodium chloride aqueous solution respectively, dried over anhydrous sodium sulfate, and separated by silica gel column chromatography to obtain 0.98g of N,N-dimethyl-3-[(benzo[1,4]dioxan- 5-yl-oxy)-3-(furan-2-yl)propylamine] as a yellow oil. The yellow oil was dissolved in 30 mL ethyl acetate, and added with oxalic acid (0.29g, 0.032mol) to generate a pale yellow precipitate. The mixture was heated to reflux, cooled to room temperature, frozen for 2h, and filtrated under vacumm. The filter cake was washed with cold ethyl acetate to obtain 0.75g of the target compound as a pale yellow powdery solid in a yield of 19.1% and a melting point of 101-103C. MS (m/e): 304.3 (M+1+), 326.2(M+Na+). 1H-NMR delta (ppm, DMSO-d6): 7.63(s,1H,5'-H); 6.62-6.66(t,1H,7-H); 6.54-6.56 (d,1H,6-H); 6.44-6.46 (d,1H,8-H); 6.39-6.40 (m,2H, 3',4'-H); 5.30-5.34(t,1H, CHO); 4.16-4.23(t,4H,2,3-H); 2.23-2.27(t,2H,CH2N); 1.99-2.23 (m,2H,CH2CH2N); 2.10 (s,6H, N(CH3)2).

Reference： [1]Patent: EP2305669,2011,A1 .Location in patent: Page/Page column 14

57
[ 10288-36-5 ]
C₈H₇Br₂O₄P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; phosphorus(V) oxybromide; In dichloromethane; at -60 - 25℃; for 2h;	A solution of tribromophosphorus (2.87 g, 10 mmol)Was dissolved in dichloromethane (20 mL)Cooled to -60 C,A solution of 5-hydroxy-2,3-dihydrobenzo [1,4] dioxane (1.52 g, 10 mmol) and triethylamine (0.81 g, 0.8 mmol) in dichloromethane (10 mL) was slowly added dropwise.After completion of the dropwise addition, the cold bath was removed and the mixture was stirred at 25 C for 2 hours.The reaction system was further cooled to -60 C, L-alanine-4-fluorobenzyl ester hydrochloride (2.72 g, 15 mmol) was added, and then a solution of triethylamine (1.42 g, 14 mmol) in dichloromethane15 mL).After completion of the dropwise addition, the cold bath was removed and the mixture was stirred at 25 C for 2 hours.The reaction system was further cooled to -60 C and a solution of pentafluorophenol (1.66 g, 9 mmol) and triethylamine (1.82 g, 18 mmol) in dichloromethane (10 mL) was added dropwise.After completion of the dropwise addition, the cold bath was removed and the mixture was stirred at 25 C for 2 hours.The reaction was complete and the reaction system was poured into ice water and extracted with dichloromethane.The combined organic phases were washed with saturated brine solution, dried and concentrated by filtration to give intermediate (S) -4-fluorobenzyl-2 - ((pentafluorophenoxy) (2,3-dihydrobenzo [4] dioxino-5-oxo) phosphoryl) amino) propionate.

Reference： [1]Patent: CN106554382,2017,A .Location in patent: Paragraph 0691

58
[ 10288-36-5 ]
C₁₈H₁₈BrFNO₆P [ No CAS ]

Reference： [1]Patent: CN106554382,2017,A

59
[ 10288-36-5 ]
C₂₄H₁₈F₆NO₇P [ No CAS ]

Reference： [1]Patent: CN106554382,2017,A

60
[ 10288-36-5 ]
C₂₈H₃₀F₂N₃O₁₁P [ No CAS ]

Reference： [1]Patent: CN106554382,2017,A

61
[ 10288-36-5 ]
C₂₈H₃₀F₂N₃O₁₁P [ No CAS ]
C₂₈H₃₀F₂N₃O₁₁P [ No CAS ]

Reference： [1]Patent: CN106554382,2017,A

62
[ 10288-36-5 ]
[ 100-39-0 ]
5-(benzyloxy)-2,3-dihydrobenzo[b][1,4]dioxine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 4693 - 4713

63
[ 10288-36-5 ]
5-(benzyloxy)-8-bromo-2,3-dihydrobenzo[b][1,4]dioxine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 4693 - 4713

64
[ 10288-36-5 ]
tert-butyl 4-[8-(benzyloxy)-2,3-dihydrobenzo[b][1,4]dioxin-5-yl]-piperazine-1-carboxylate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 4693 - 4713

65
[ 10288-36-5 ]
1-[8-(benzyloxy)-2,3-dihydrobenzo[b][1,4]dioxin-5-yl]piperazine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 4693 - 4713

66
[ 10288-36-5 ]
7-(4-{4-[8-(benzyloxy)-2,3-dihydrobenzo[b][1,4]dioxin-5-yl]-piperazin-1-yl}butoxy)-3,4-dihydroquinolin-2(1H)-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 4693 - 4713

67
[ 10288-36-5 ]
7-(4-[4-(8-hydroxy-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)-piperazin-1-yl]butoxy)-3,4-dihydroquinolin-2(1H)-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 4693 - 4713

68
[ 10288-36-5 ]
5-(4-{4-[8-(benzyloxy)-2,3-dihydrobenzo[b][1,4]dioxin-5-yl]-piperazin-1-yl}butoxy)pyrazolo[1,5-a]pyridine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 4693 - 4713

69
[ 10288-36-5 ]
5-(4-[4-(8-hydroxy-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)-piperazin-1-yl]butoxy)pyrazolo[1,5-a]pyridine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 4693 - 4713

70
[ 10288-36-5 ]
[ 24313-88-0 ]
(E)-8-((3,4,5-trimethoxyphenyl)diazenyl)-2,3-dihydrobenzo[b][1,4]dioxin-5-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%		General procedure: 3,4,5-trimethoxyaniline (0.183 g, 1 mmol) was dissolved either in ethanol or water (5 mL) and cooled inice bath to -10 C. Then concentrated (37%) HCl (1 mL) was added dropwise and keep stirrer thesolution for 5 minutes. An ice-cold aqueous solution (5 mL) of NaNO2 (0.139 g, 2 mmol) was preparedand cooled at below -10 C in ice bath, concentrated (37%) HCl (1 mL) was added and then this solutionwas added dropwise to the aniline solution. The reacction mixture stirred in ice bath for one hour toprepare diazonium salt. Another basic solution of required phenolic compound (0.9 mmol) was preparedin aqueous solution of NaOH (0.800 g, 5 mL) and cooled in an ice bath to below -10 C. This cold basicphenolic solution was added dropwise into chilled diazonium salt solution. Then additional NaOH wasadded to neutralize the pH and then ice bath was removed. Further, reaction mixture was stirred foranother 2h at room temperature (r.t.). Afterwards the reaction mixture was acidifed by addition aqueousHCl (1N) and the product was extracted from aqueous solution using ethylacetate (50 mL x 3). Organiclayers were combined and washed with water (20 mL x 2), brine (20 mL x 2), dried over anhydrousNaSO4 and solvent was removed under vacuum. The product was purified through flash silica gel columnchromatography using ethylacetate/hexane mixture.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 143,p. 1 - 7

71
[ 10288-36-5 ]
[ 24313-88-0 ]
(E)-1-(8-methoxy-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)-2-(3,4,5 trimethoxyphenyl)diazene [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 143,p. 1 - 7

72
[ 10288-36-5 ]
[ 50845-77-7 ]
ethyl2-(5-hydroxy-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-2-((4-methoxyphenyl)amino)acetate [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 4452 - 4456

73
[ 10288-36-5 ]
[ 2960-66-9 ]
C₁₄H₁₆O₆ [ No CAS ]
C₁₄H₁₆O₆ [ No CAS ]

Reference： [1]Chemical Communications,2019,vol. 55,p. 5171 - 5174

74
[ 50-00-0 ]
[ 10288-36-5 ]
[ 123373-35-3 ]

Yield	Reaction Conditions	Operation in experiment
60%	With triethylamine; magnesium chloride; In acetonitrile; at 0℃; for 4h;Reflux;	To a stirred solution of compound 2 (1 Og, 65.78mmol, 1 eq), in ACN (200ml_), was added TEA (35ml_, 263mmol, 4eq) followed by MgCh (9.3g, 98.68mmol, 1.5eq) at RT. The reaction mixture was cooled to 0 C and para formaldehyde (13.8g, 460.5mmol, 7eq) was added and the resulting reaction mixture was refluxed for 4h. The reaction was monitored by TLC. TLC analysis indicated formation of a non-polar spot. The reaction mixture was cooled to 0 C, acidified with aq 2N HCI solution and extracted with ethyl acetate. The combined organic layer was dried over Na2S04 and concentrated under reduced pressure to give Compound 3 (7g, 60% yield) as pale yellow liquid. LCMS: m/z 181 .33 (M+H):

Reference： [1]Patent: WO2019/153080,2019,A1 .Location in patent: Paragraph 00309

75
[ 10288-36-5 ]
C₉H₈O₅ [ No CAS ]

Reference： [1]Patent: WO2019/153080,2019,A1

76
[ 10288-36-5 ]
C₁₇H₂₅NO₄ [ No CAS ]

Reference： [1]Patent: WO2019/153080,2019,A1

77
[ 10288-36-5 ]
C₁₇H₂₄BrNO₄ [ No CAS ]

Reference： [1]Patent: WO2019/153080,2019,A1

78
[ 10288-36-5 ]
C₂₂H₃₆BrNO₄Si [ No CAS ]

Reference： [1]Patent: WO2019/153080,2019,A1

79
[ 10288-36-5 ]
8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(2,4,4-trimethylpentan-2-yl)-5-(2-(trimethylsilyl)ethoxy)-2,3-dihydrobenzo[b][1,4]dioxine-6-carboxamide [ No CAS ]

Reference： [1]Patent: WO2019/153080,2019,A1

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H200	Unstable explosive
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H202	Explosive; severe projection hazard
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H301	Toxic if swallowed
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H303	May be harmful if swallowed
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H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
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H341	Suspected of causing genetic defects
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H361	Suspected of damaging fertility or the unborn child
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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
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H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 10288-36-5 ] {[proInfo.proName]}

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[ 10288-36-5 ] Synthesis Path-Upstream 1~3

[ 10288-36-5 ] Synthesis Path-Downstream 1~79

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Alcohols

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Benzodioxans

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