[ CAS No. 104594-70-9 ] {[proInfo.proName]}

Name: 104594-70-9|Phenethyl 3-(3,4-dihydroxyphenyl)acrylate|98%
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Quality Control of [ 104594-70-9 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 104594-70-9 ]

CAS No. :	104594-70-9	MDL No. :	MFCD00866470
Formula :	C₁₇H₁₆O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SWUARLUWKZWEBQ-VQHVLOKHSA-N
M.W :	284.31	Pubchem ID :	5281787
Synonyms :	Caffeic acid phenethyl ester;CAPE;BAF-IN-C09;β-Phenylethyl Caffeate;2-Phenylethyl Caffeate;Caffeic Acid phenylethyl ester;Phenylethyl Caffeate	Chemical Name :	Phenethyl 3-(3,4-dihydroxyphenyl)acrylate

Safety of [ 104594-70-9 ]

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 [ 104594-70-9 ]

* 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 [ 104594-70-9 ]
Downstream synthetic route of [ 104594-70-9 ]

[ 104594-70-9 ] Synthesis Path-Upstream 1~13

1
[ 118971-54-3 ]
[ 104594-70-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	With pyrrolidine In tetrahydrofuran at 20℃; for 0.5 h;	To a solution of (E)-4-(3-oxo-3-phenethoxyprop-1-enyl)-1,2-phenylene diacetate 11a (474 mg, 1.29 mmol, 1 eq) in anhydrous THF (15 mL) was added pyrrolidine (cat). After stirring at room temperature for 30 min, water (10 mL) was added and the reaction mixture was extracted with EtOAc (20 mL). The combined organic layers were washed with 1 N HCl (7 * 20 mL), brine. After drying (Na₂SO₄) and concentration under reduced pressure, CAPE 3 was obtained as a yellow powder (36.7 mg, 75percent). Mp 125.5 °C. R_f = 0.75 (SiO₂, 40percent EtOAc/cyclohexane). ¹H NMR (400 MHz, Acetone-d₆) δ 8.36 (br s, 1H), 8.08 (br s, 1H), 7.6 (d, J = 15.0 Hz, 1H) 7.40 (dd, J = 9.0, 2.0 Hz, 1H), 7.35-7.28 (m, 5H), 7.25 (d, J = 2.0 Hz, 1H), 7.20 (d, J = 9.0 Hz, 1H), 6.30 (d, J = 15.0 Hz, 1H), 4.35 (t, J = 7.0 Hz, 2H), 2.90 (t, J = 7.0 Hz, 2H). ¹³C NMR (101 MHz, Acetone-d₆) δ 167.4, 148.9, 148.4, 145.9, 139.4, 129.9, 129.4, 127.7, 127.3, 122.6, 116.5, 115.6, 115.3, 65.4, 35.9.

Reference： [1] European Journal of Medicinal Chemistry, 2014, vol. 75, p. 391 - 402

2
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Yield	Reaction Conditions	Operation in experiment
270 g	With piperidine In pyridine; toluene at 95℃; for 15 h;	Add 1L of toluene to the 3L reaction flask,SM1 (cyclopropane (isopropyl) isopropyl ester, 240 g, commercially available) was added in succession under mechanical stirringAnd SM2 (phenylethanol, 202 g, commercially available),After the addition,Warm up to 100°C to start timingStop the reaction after 8 hoursCool naturally to cool down to room temperatureSM3 (3,4-dihydroxybenzaldehyde, 160 g, commercially available) was added while stirring was continued.Then add pyridine 166ml and piperidine 17ml,Then it warms up to an internal temperature of 95°C.The reaction was stopped after 15 hours of reaction.Cool down to room temperatureAfter adding 1 L of ethyl acetate, the organic phase was washed successively with 1 L of 1M hydrochloric acid solution and 1 L of saturated saline, and the organic phase was dried over anhydrous sodium sulfate for 30 minutes, filtered, and the organic solvent was evaporated in vacuo to obtain a crude product. 2L n-hexane was filtered after beatingThe cake was vacuum dried in a box at 40°C for 24 hours to give 270 g of a product of caffeic acid phenylethyl ester.

Reference： [1] Journal of Chemical Research, 2005, # 5, p. 332 - 334
[2] Journal of Chemical Research, 2006, # 9, p. 586 - 588
[3] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 24, p. 6553 - 6557
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 18, p. 4367 - 4371
[5] Patent: CN107337604, 2017, A, . Location in patent: Paragraph 0071; 0072; 0073; 0074

3
[ 60-12-8 ]
[ 331-39-5 ]
[ 104594-70-9 ]

Yield	Reaction Conditions	Operation in experiment
48%	With ytterbium(III) triflate In nitromethane at 120℃; for 0.666667 h;	To a mixture of caffeic acid fine powder (1.0 g, 5.56 mmol, 1.0 equiv.),alcohol (5.56 mmol, 1.0 equiv.) in nitromethane (125 mL) was addedytterbium triflate (34.4 mg, 0.056 mmol, 0.01 equiv.). After 5 min inan ultrasonic bath the mixture without protective gas was stirred ona 120 °C oil bath for a given time. The reaction mixture was cooled toroom temperature, washed with deionised water (30 mL), 2percent NaHCO3(30 mL) and brine, dried over anhydrous Na2SO4 and evaporated underreduced pressure to give the crude product, which was purified on asilica gel column to give the compounds 1–5 and 8–30.2-Phenethyl (E)-3-(3,4-dihydroxyphenyl) acrylate (1): Whitesolid; yield 758 mg, 48.0percent; m.p. 128–130 °C (lit.20 116–123 °C);IR (KBr) νmax 3480, 3328, 1683, 1601, 1362, 1301, 1279, 1182 cm–1;1H NMR (400 MHz, DMSO-d6) δH 7.46 (1H, d, J = 16 Hz, CH=CHCO),7.34–7.18 (5H, m, C6H5), 7.05 (1H, s, 2‑ArH), 6.99 (1H, d, J = 8.0 Hz,6‑ArH), 6.77 (1H, d, J = 8.0 Hz, 5‑ArH), 6.24 (1H, d, J = 16 Hz,CH=CHCO), 4.32 (2H, t, J = 6.8 Hz, OCH2), 2.94 (2H, t, J = 6.8 Hz,OCH2CH2) ppm; 13C NMR (100 MHz, DMSO-d6) δC 166.4, 148.3,145.4, 145.1, 138.0, 128.8, 128.3, 126.3, 125.4, 121.4, 115.7, 114.7, 113.8,64.3, 34.4 ppm; HRMS-ESI C17H16O4 calcd [M–H]– 283.0970, found283.0966.
48%	With ytterbium(III) triflate In nitromethane at 120℃;	General procedure: To a mixture of caffeic acid fine powder (1.0 g, 5.56 mmol), various phenethyl alcohols (5.56 mmol) in CH₃NO₂ (125 mL) was added Yb(OTf)₃ (34.4 mg, 0.056 mmol). After 5 min of ultrasonic shake, the mixture was stirred on a 120 °C oil bath for 40-120 min. The reaction mixture was cooled to room temperature, washed with 2percent NaHCO₃ (30 mL) and brine, dried over anhydrous Na₂SO₄, and concentrated to give crude products, which were purified by column chromatography to give the compounds 1-26 in 18-61percent yields. Phenethyl (E)-3-(3,4-dihydroxyphenyl) acrylate (CAPE). White solid (48percent yield for esterification reaction); Mp 128–130 °C; ¹H NMR (400 MHz, DMSO-d₆) δ_H 7.46 (1H, d, J = 16.0 Hz, CH=CHCO), 7.34-7.18 (5H, m, C₆H₅), 7.05 (1H, s, 2-ArH), 6.99 (1H, d, J = 8.0 Hz, 5-ArH), 6.77 (1H, d, J = 8.0 Hz, 6-ArH), 6.24 (1H, d, J = 16.0 Hz, CH=CHCO), 4.32 (2H, t, J = 6.8 Hz, OCH₂), 2.94 (2H, t, J = 6.8 Hz, CH₂C₆H₅) ppm; ¹³C NMR (100 MHz, DMSO-d₆) δ_C 166.4, 148.3, 145.4, 145.1, 138.0, 128.8, 128.3, 126.3, 125.4, 121.4, 115.7, 114.7, 113.8, 64.3, 34.4 ppm; HRMS-ESI C₁₇H₁₆O₄ calcd [M-H]^- 283.0970, found 283.0966.

Reference： [1] Patent: EP1211237, 2002, A1, . Location in patent: Example 1
[2] Organic Letters, 2002, vol. 4, # 22, p. 3839 - 3841
[3] Journal of Chemical Research, 2014, vol. 38, # 11, p. 695 - 700
[4] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 131 - 134
[5] Patent: EP1211237, 2002, A1, . Location in patent: Page 5
[6] Patent: EP1211237, 2002, A1, . Location in patent: Page 5
[7] Journal of Medicinal Chemistry, 1995, vol. 38, # 21, p. 4171 - 4178
[8] Patent: US5610185, 1997, A,
[9] Chemical and Pharmaceutical Bulletin, 2017, vol. 65, # 11, p. 1020 - 1027

4
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[ 103-63-9 ]
[ 104594-70-9 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 2001, vol. 49, # 2, p. 236 - 238
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 16, p. 7584 - 7597
[3] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 1, p. 199 - 209

5
[ 331-39-5 ]
[ 104594-70-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 10, p. 3351 - 3359
[2] European Journal of Medicinal Chemistry, 2014, vol. 75, p. 391 - 402

6
[ 60-12-8 ]
[ 77201-71-9 ]
[ 104594-70-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 10, p. 3351 - 3359
[2] Patent: EP1211237, 2002, A1, . Location in patent: Page 5

7
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Reference： [1] Russian Journal of Bioorganic Chemistry, 1995, vol. 21, # 2, p. 124 - 131[2] Bioorganicheskaya Khimiya, 1995, vol. 21, # 2, p. 143 - 151

8
[ 60-12-8 ]
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Reference： [1] Journal of Chemical Research, 2006, # 9, p. 586 - 588
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 18, p. 4367 - 4371

9
[ 92778-42-2 ]
[ 104594-70-9 ]

Reference： [1] Journal of Chemical Research, 2005, # 5, p. 332 - 334

10
[ 88623-81-8 ]
[ 104594-70-9 ]

Reference： [1] European Journal of Medicinal Chemistry, 2014, vol. 75, p. 391 - 402

11
[ 621-59-0 ]
[ 104594-70-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 18, p. 4367 - 4371

12
[ 103-82-2 ]
[ 104594-70-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 131 - 134

13
[ 331-39-5 ]
[ 538-75-0 ]
[ 104594-70-9 ]

Reference： [1] Russian Journal of Bioorganic Chemistry, 1995, vol. 21, # 2, p. 124 - 131[2] Bioorganicheskaya Khimiya, 1995, vol. 21, # 2, p. 143 - 151

[ 104594-70-9 ] Synthesis Path-Downstream 1~20

1
[ 60-12-8 ]
[ 331-39-5 ]
[ 104594-70-9 ]
N,N'-dicyclohexyl-O-(3,4-dihydrocinnamoyl)isourea [ No CAS ]

Reference： [1]Russian Journal of Bioorganic Chemistry,1995,vol. 21,p. 124 - 131
Bioorganicheskaya Khimiya,1995,vol. 21,p. 143 - 151

2
[ 331-39-5 ]
[ 538-75-0 ]
[ 104594-70-9 ]
N,N'-dicyclohexyl-O-(3,4-dihydrocinnamoyl)isourea [ No CAS ]

Reference： [1]Russian Journal of Bioorganic Chemistry,1995,vol. 21,p. 124 - 131
Bioorganicheskaya Khimiya,1995,vol. 21,p. 143 - 151

3
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Yield	Reaction Conditions	Operation in experiment
48%	With ytterbium(III) triflate; In nitromethane; at 120℃; for 0.666667h;Catalytic behavior;	To a mixture of caffeic acid fine powder (1.0 g, 5.56 mmol, 1.0 equiv.),alcohol (5.56 mmol, 1.0 equiv.) in nitromethane (125 mL) was addedytterbium triflate (34.4 mg, 0.056 mmol, 0.01 equiv.). After 5 min inan ultrasonic bath the mixture without protective gas was stirred ona 120 C oil bath for a given time. The reaction mixture was cooled toroom temperature, washed with deionised water (30 mL), 2% NaHCO3(30 mL) and brine, dried over anhydrous Na2SO4 and evaporated underreduced pressure to give the crude product, which was purified on asilica gel column to give the compounds 1-5 and 8-30.2-Phenethyl (E)-3-(3,4-dihydroxyphenyl) acrylate (1): Whitesolid; yield 758 mg, 48.0%; m.p. 128-130 C (lit.20 116-123 C);IR (KBr) numax 3480, 3328, 1683, 1601, 1362, 1301, 1279, 1182 cm-1;1H NMR (400 MHz, DMSO-d6) deltaH 7.46 (1H, d, J = 16 Hz, CH=CHCO),7.34-7.18 (5H, m, C6H5), 7.05 (1H, s, 2-ArH), 6.99 (1H, d, J = 8.0 Hz,6-ArH), 6.77 (1H, d, J = 8.0 Hz, 5-ArH), 6.24 (1H, d, J = 16 Hz,CH=CHCO), 4.32 (2H, t, J = 6.8 Hz, OCH2), 2.94 (2H, t, J = 6.8 Hz,OCH2CH2) ppm; 13C NMR (100 MHz, DMSO-d6) deltaC 166.4, 148.3,145.4, 145.1, 138.0, 128.8, 128.3, 126.3, 125.4, 121.4, 115.7, 114.7, 113.8,64.3, 34.4 ppm; HRMS-ESI C17H16O4 calcd [M-H]- 283.0970, found283.0966.
48%	With ytterbium(III) triflate; In nitromethane; at 120℃;	General procedure: To a mixture of caffeic acid fine powder (1.0 g, 5.56 mmol), various phenethyl alcohols (5.56 mmol) in CH3NO2 (125 mL) was added Yb(OTf)3 (34.4 mg, 0.056 mmol). After 5 min of ultrasonic shake, the mixture was stirred on a 120 C oil bath for 40-120 min. The reaction mixture was cooled to room temperature, washed with 2% NaHCO3 (30 mL) and brine, dried over anhydrous Na2SO4, and concentrated to give crude products, which were purified by column chromatography to give the compounds 1-26 in 18-61% yields. Phenethyl (E)-3-(3,4-dihydroxyphenyl) acrylate (CAPE). White solid (48% yield for esterification reaction); Mp 128-130 C; 1H NMR (400 MHz, DMSO-d6) deltaH 7.46 (1H, d, J = 16.0 Hz, CH=CHCO), 7.34-7.18 (5H, m, C6H5), 7.05 (1H, s, 2-ArH), 6.99 (1H, d, J = 8.0 Hz, 5-ArH), 6.77 (1H, d, J = 8.0 Hz, 6-ArH), 6.24 (1H, d, J = 16.0 Hz, CH=CHCO), 4.32 (2H, t, J = 6.8 Hz, OCH2), 2.94 (2H, t, J = 6.8 Hz, CH2C6H5) ppm; 13C NMR (100 MHz, DMSO-d6) deltaC 166.4, 148.3, 145.4, 145.1, 138.0, 128.8, 128.3, 126.3, 125.4, 121.4, 115.7, 114.7, 113.8, 64.3, 34.4 ppm; HRMS-ESI C17H16O4 calcd [M-H]- 283.0970, found 283.0966.
9%	With ytterbium(III) triflate; In nitromethane; for 1.5h;Reflux;	Caffeic acid (0.5 g, 2.78 mmol) and 2-phenylethanol (0.35 mL,2.78 mmol) were dissolved in nitromethane (62.5 mL). Yb(OTf)3(0.017 g, 0.028 mmol) was added, and the suspension was stirredfor 5 min in an ultrasonic bath followed by an additional 1.5 hstirring under reflux [4]. The reaction mixture was stirred at roomtemperature overnight and washed with NaHCO3-solution (2%,15 mL) and brine (15 mL). The organic phase was dried over Na2SO4and concentrated under reduced pressure. The crude product waspurified by column chromatography (silica gel; chloroform/methanol,99:1), and compound 17 was obtained as a white solid (0.07 g,9%); RF 0.04 (silica gel; chloroform/methanol, 99:1); m.p.128-130 C (lit.: [19]: 126-128 C); IR (KBr): nu 3480s, 1685m,1636m, 1602s, 1535w, 1442w, 1363w, 1302m, 1279s, 1182s cm1;UV-vis (CHCl3): lambda (log epsilon) 250 (4.06), 320 (4.21), 353 (4.28) nm; 1HNMR (500 MHz, CDCl3): delta 7.56 (d, J 15.9 Hz, 1H, 3-H), 7.34-7.30(m, 2H, 2-H), 7.27-7.22 (m, 3H, 3-H4-H), 7.07 (d, J 2.0 Hz, 1H, 50-H), 7.01 (dd, J 8.2, 2.0 Hz, 1H, 20-H), 6.87 (d, J 8.2 Hz, 1H, 60-H),6.25 (d, J 15.9 Hz, 1H, 2-H), 4.42 (t, J 7.1 Hz, 2H, 1-H), 3.01 (t,J 7.1 Hz, 2H, 2-H); 13C NMR (125 MHz, CDCl3): delta 167.8 (C-1),146.5 (C-40), 145.2 (C-30), 143.9 (C-3), 138.0 (C-1), 129.1 (C-3), 128.7(C-2), 127.7 (C-10), 126.8 (C-4), 122.7 (C-60), 115.7 (C-2), 115.6 (C-50),144.6 (C-20), 65.3 (C-1), 35.4 (C-2) ppm; MS (ESI, MeOH): m/z(%) 285.0 ([MH], 45), 302.2 ([MNH4], 23), 307.1 ([MNa],100), 446.1 ([3 MKH]2, 44), 580.1 ([4 MNaH]2, 23), 588.0([4MKH]2, 50), 590.8 ([2MNa], 42), 599.9 ([4MZn]2, 48);analysis calcd for C17H16O4 (284.31): C 71.82, H 5.67; found: C 71.69,H 5.83.

	With toluene-4-sulfonic acid; In benzene;	Synthesis of Cinnamic Acid Analogues. The synthesis of cinnamic acid analogues was achieved by straight forward application of literature techniques. Two general approaches, designated "method A" and "method B" were utilized: Method A: Synthesis of Caffeic acid beta-phenylethyl ester (CAPE, 67H-42-A). A solution of 1.80 g (10.0 mmol) of caffeic acid, 17.9 mL (150 mmol) of beta-phenylethyl alcohol and 100 mg of p-toluenesulfonic acid in benzene (100 mL) were stirred overnight at reflux with a Dean Stark trap. Solvent and excess alcohol were removed by distillation and residue purified by silica gel chromatography (petroleum ether/CHCl3). Product was crystallized (ether/petroleum ether) to provide 67H-42-A as snow-white crystals, 1.0 g (35%): mp 128.0 C. 126-128 C.) (Grunberger, D. et al., Experimentia, (1988) 44:230-2).
	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 48h;	General procedure: Cinnamicacid esters (13-22) were synthesized according to a modified previous procedure.31) To a mixture of cinnamic acid derivatives (Ia-d, 3.0 mmol) and the appropriate alcohol (2.0 mmol)in dry tetrahydrofuran (6mL) were added triphenylphosphine (3.0 mmol) and diisopropyl azodicarboxylate (DIAD(3.0mmol). The reaction mixture was stirred for 48h at room temperature and the whole mixture was extracted with AcOEt and saturated NaHCO3 solution, and the organic extract was washed with brine.The organic layer was dried overNa2SO4 and the solvent was evaporated under reduced pressure. The residue was then purified by silica gel column chromatography (hexane:AcOEt=2:1)to give the title compound.

Reference： [1]Patent: EP1211237,2002,A1 .Location in patent: Example 1
[2]Organic Letters,2002,vol. 4,p. 3839 - 3841
[3]Journal of Chemical Research,2014,vol. 38,p. 695 - 700
[4]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 131 - 134
[5]Patent: EP1211237,2002,A1 .Location in patent: Page 5
[6]Patent: EP1211237,2002,A1 .Location in patent: Page 5
[7]Journal of Medicinal Chemistry,1995,vol. 38,p. 4171 - 4178
[8]European Journal of Medicinal Chemistry,2019,vol. 177,p. 259 - 268
[9]Patent: US5610185,1997,A
[10]Chemical and Pharmaceutical Bulletin,2017,vol. 65,p. 1020 - 1027
[11]Journal of Agricultural and Food Chemistry,2019,vol. 67,p. 2028 - 2035

4
[ 104594-70-9 ]
2-phenylethyl 3-(3,4-dihydroxyphenyl)propanoate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 4171 - 4178
[2]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 199 - 209

5
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[ 103-63-9 ]
[ 104594-70-9 ]

Yield	Reaction Conditions	Operation in experiment
67%		General procedure: To a stirredsolution of the acid (1 mmol) in dry hexamethyl phosphoramide (5 mL), Nua2CO3 (126 mg, 1.19 mmol) wasadded and stirring continued for 30 min. At the end of this period, thecorresponding bromide (1.14 mmol) was added to the reaction mixture followed bya catalytic amount of potassium iodide. The mixture was stirred at room temperaturefor 48 h, after which EtOAc (30 ml) and HCl 0.5 N (5 mL) were added. Theorganic phase was washed with brine, dried over Na2SO4,filtered and concentrated under reduced pressure. The crude product waspurified by column chromatography.

Reference： [1]Chemical and Pharmaceutical Bulletin,2001,vol. 49,p. 236 - 238
[2]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 1085 - 1089
[3]Journal of Medicinal Chemistry,2016,vol. 59,p. 7584 - 7597
[4]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 199 - 209

6
[ 60-12-8 ]
[ 77201-71-9 ]
[ 104594-70-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 3351 - 3359
[2]Patent: EP1211237,2002,A1 .Location in patent: Page 5

7
[ 139-85-5 ]
[ 848598-50-5 ]
[ 104594-70-9 ]

Yield	Reaction Conditions	Operation in experiment
	With piperidine; pyridine; at 20℃;	General procedure: The Meldrum?s acid (3.6g, 25mmol) was added into toluene (50ml), then added alcohol or phenol (25mmol). The mixture was heated and refluxed for 5 hrs. When the mixture was cooled to room temperature, added substituted benzaldehyde (10mmol), pyridine (2.5ml) and piperidine (0.25ml). The stirring continued at room temperature, using TLC to trace the reaction until the reaction completely finished. The solvents were distilled out in vacuum; the residue was dissolved in diethyl ether (about 30ml), washed with saturated solution of sodium bicarbonate two times (20ml×2), then diluted hydrochloride acid and distilled water, respectively. The ether phase was driedby anhydrous MgSO4 overnight. After removal of the drier, the solvent was distilled out to get crude solid. (If the crude product was oil, dissolved in dichloromethane (10ml) and then was subjected to chromatograph on a silica gel column (15 g), eluted with ethyl acetate and petroleum ether 1:15. The eluted fraction was distilled outto get crude product. ) The crude solid was recrystallized from a mixture of benzene and diethyl ether (8:2) to afford pure product.
270 g	With piperidine; In pyridine; toluene; at 95℃; for 15h;	Add 1L of toluene to the 3L reaction flask,SM1 (cyclopropane (isopropyl) isopropyl ester, 240 g, commercially available) was added in succession under mechanical stirringAnd SM2 (phenylethanol, 202 g, commercially available),After the addition,Warm up to 100C to start timingStop the reaction after 8 hoursCool naturally to cool down to room temperatureSM3 (3,4-dihydroxybenzaldehyde, 160 g, commercially available) was added while stirring was continued.Then add pyridine 166ml and piperidine 17ml,Then it warms up to an internal temperature of 95C.The reaction was stopped after 15 hours of reaction.Cool down to room temperatureAfter adding 1 L of ethyl acetate, the organic phase was washed successively with 1 L of 1M hydrochloric acid solution and 1 L of saturated saline, and the organic phase was dried over anhydrous sodium sulfate for 30 minutes, filtered, and the organic solvent was evaporated in vacuo to obtain a crude product. 2L n-hexane was filtered after beatingThe cake was vacuum dried in a box at 40C for 24 hours to give 270 g of a product of caffeic acid phenylethyl ester.
		General procedure: The desired amount of malonic acid mono esters (0.6 mmol, 1.2 equiv.) was dissolved in toluene (1 mL) followed by the addition of pyridine (12.5 mmol, 25 equiv., 1 mL) and piperidine (0.80 mmol, 1.6 equiv., 79 muL). This mixture was stirred at r.t. for 10 min to form enolates before the desired aldehyde (0.5 mmol,1.0 equiv.) was added at 0C. The reaction mixture was continued to bestirred at r.t. for 1?6 days. TLC was used to monitor the reaction progress. Once the reaction was complete, the reaction mixture was transferred to a separatory funnel using EtOAc (15 mL) and washed with 5% HCl (10 mL×2) and distilled water (10 mL×2). After removalof the ethyl acetate by rotatory evaporation, the crude product was purified by automated flash chromatography, eluting with an ethylacetate/hexanes or methanol/methylene chloride gradient to afford the desired products.

Reference： [1]Journal of Chemical Research,2005,p. 332 - 334
[2]Journal of Chemical Research,2006,p. 586 - 588
[3]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 6553 - 6557
[4]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 4367 - 4371
[5]Patent: CN107337604,2017,A .Location in patent: Paragraph 0071; 0072; 0073; 0074
[6]Bioorganic Chemistry,2019,vol. 86,p. 686 - 695

8
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C₁₇H₁₅O₄ [ No CAS ]
C₁₇H₁₄O₄^(1-) [ No CAS ]

Reference： [1]Journal of Agricultural and Food Chemistry,2006,vol. 54,p. 2932 - 2937

9
[ 60-12-8 ]
[ 104594-70-9 ]

Reference： [1]Journal of Chemical Research,2006,p. 586 - 588
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 4367 - 4371
[3]Bioorganic Chemistry,2019,vol. 86,p. 686 - 695

10
[ 92778-42-2 ]
[ 104594-70-9 ]

Reference： [1]Journal of Chemical Research,2005,p. 332 - 334

11
[ 331-39-5 ]
[ 104594-70-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 3351 - 3359
[2]European Journal of Medicinal Chemistry,2014,vol. 75,p. 391 - 402

12
C₃₀H₂₄O₃ [ No CAS ]
[ 104594-70-9 ]

Reference： [1]Patent: EP1211237,2002,A1 .Location in patent: Page 5

14
[ 118971-54-3 ]
[ 104594-70-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	With pyrrolidine; In tetrahydrofuran; at 20℃; for 0.5h;	To a solution of (E)-4-(3-oxo-3-phenethoxyprop-1-enyl)-1,2-phenylene diacetate 11a (474 mg, 1.29 mmol, 1 eq) in anhydrous THF (15 mL) was added pyrrolidine (cat). After stirring at room temperature for 30 min, water (10 mL) was added and the reaction mixture was extracted with EtOAc (20 mL). The combined organic layers were washed with 1 N HCl (7 * 20 mL), brine. After drying (Na2SO4) and concentration under reduced pressure, CAPE 3 was obtained as a yellow powder (36.7 mg, 75%). Mp 125.5 C. Rf = 0.75 (SiO2, 40% EtOAc/cyclohexane). 1H NMR (400 MHz, Acetone-d6) delta 8.36 (br s, 1H), 8.08 (br s, 1H), 7.6 (d, J = 15.0 Hz, 1H) 7.40 (dd, J = 9.0, 2.0 Hz, 1H), 7.35-7.28 (m, 5H), 7.25 (d, J = 2.0 Hz, 1H), 7.20 (d, J = 9.0 Hz, 1H), 6.30 (d, J = 15.0 Hz, 1H), 4.35 (t, J = 7.0 Hz, 2H), 2.90 (t, J = 7.0 Hz, 2H). 13C NMR (101 MHz, Acetone-d6) delta 167.4, 148.9, 148.4, 145.9, 139.4, 129.9, 129.4, 127.7, 127.3, 122.6, 116.5, 115.6, 115.3, 65.4, 35.9.

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 75,p. 391 - 402

15
[ 88623-81-8 ]
[ 104594-70-9 ]

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 75,p. 391 - 402

16
[ 621-59-0 ]
[ 104594-70-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 4367 - 4371

17
[ 104594-70-9 ]
[ 5538-51-2 ]
3-[3,4-bis[2-(acetyloxy)benzoyloxy]phenyl]-(2E)-2-propenoic acid 2-phenylethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 22℃; for 4h;Inert atmosphere;	Fig. 2 shows the synthesis of VP939. A solution of CAPE (500mg, 1.76mmol) and N,N-diisopropylethylamine (0.67ml, 3.87mmol) in 7ml of anhydrous tetrahydrofurane (THF) was added drop-wise to a solution of 2-(acetyloxy)benzoyl chloride (Sigma Aldrich, Italy; 769mg, 3.87mmol) in anhydrous THF (2ml) and the mixture was stirred under nitrogen for 4h at 22C. After removing the THF, the mixture was dissolved in ethyl acetate. The obtained organic phase was washed with water (2×75ml) followed by saturated sodium chloride solution, dried over sodium sulfate, filtered, and evaporated. The isolated crude material was purified by column chromatography (silica gel 60, 230-400mesh, Merck) using ethyl acetate/cyclohexane (3:7) as eluant. The title compound was obtained as a colorless sticky oil (861mg, 81%): IR (KBr) cm-1 3055, 2987, 1752, 1717, 1607, 1265, 1243, 1193, 1112, 1037, and 739; 1H NMR (DMSO-d6) delta 8.07-7.90 (m, 3H, aromatic), 7.83-7.64 (m, 3H+1H, aromatic+CH=CHCOO), 7.53-7.45 (m, 1H, aromatic), 7.42-7.18 (m, 9H, aromatic), 6.71 (d, J=16.0, 1H, CH=CHCOO), 4.38 (t, J=6.8Hz, 2H, OCH2CH2Ph), 2.98 (t, J=6.8Hz, 2H, OCH2CH2Ph), 2.21 (s, 3H, OCOCH3), 2.20 (s, 3H, OCOCH3). Anal. (C35H28O10) C, H.

Reference： [1]European Journal of Pharmacology,2015,vol. 752,p. 78 - 83

18
[ 104594-70-9 ]
[ 20357-37-3 ]
3-[3,4-bis[2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetyloxy]phenyl]-(2E)-2-propenoic acid 2-phenylethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
449 mg	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 22℃; for 4h;Inert atmosphere;	Fig. 3 shows the synthesis of VP964. A solution of thionyl chloride (0.203ml, 2.80mmol) in 1.5ml of anhydrous toluene was slowly added to a solution of 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid (indomethacin, Sigma Aldrich, Italy, 500mg, 1.40mmol) in 6ml of anhydrous toluene cooled at 0C and under nitrogen atmosphere. The mixture was then stirred under nitrogen, for 4h, at reflux. After this period, toluene was removed and the obtained mixture was used in the subsequent step without any further purification. A solution of CAPE (180mg, 0.635mmol) and N,N-diisopropylethylamine (0.44ml, 2.54mmol) in 6ml of anhydrous THF was added drop-wise to crude 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetyl chloride dissolved in anhydrous THF (2ml) and the mixture was stirred under nitrogen for 4h at 22C. After removing the THF, the mixture was dissolved in ethyl acetate. The obtained organic phase was washed with water (2×75ml) followed by saturated sodium chloride solution, dried over sodium sulfate, filtered, and evaporated. The isolated crude material was purified by column chromatography (silica gel 60, 230-400mesh, Merck) using ethyl acetate/cyclohexane (3:7) as eluant. The title compound was obtained as white solid (449mg, 74%): mp 80-81C; IR (KBr) cm-1 3424, 2933, 1769, 1685, 1594, 1478, 1359, 1319, 1242, 1112, 835, and 752; 1H NMR (DMSO-d6) delta 7.74-7.55 (s, 10H+1H, aromatic+CH=CHCOO), 7.37-7.16 (m, 6H, aromatic), 7.11-7.05 (m, 2H, aromatic), 6.97-6.88 (m, 2H, aromatic), 6.77-6.71 (m, 2H, aromatic), 6.61 (d, J=16.0, 1H, CH=CHCOO), 4.36 (t, J=6.8Hz, 2H, OCH2CH2Ph), 3.92 (s, 2H+2H, CH2COO+CH2COO), 3.70 (s, 3H+3H, OCH3+OCH3), 2.96 (t, J=6.8Hz, 2H, OCH2CH2Ph), 2.20 (s, 3H, CH3). 2.17 (s, 3H, CH3). Anal. (C55H44Cl2N2O10) C, H, N.

Reference： [1]European Journal of Pharmacology,2015,vol. 752,p. 78 - 83

19
[ 103-82-2 ]
[ 104594-70-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 131 - 134

20
[ 104594-70-9 ]
[ 57-50-1 ]
C₂₃H₂₆O₉ [ No CAS ]
C₂₉H₃₆O₁₄ [ No CAS ]

Reference： [1]Journal of Agricultural and Food Chemistry,2019,vol. 67,p. 4505 - 4512

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P362	Take off contaminated clothing and wash before reuse.
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P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
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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.
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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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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.
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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.
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P370 + P376	In case of fire: Stop leak if safe to Do so.
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H204	Fire or projection hazard
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H221	Flammable gas
H222	Extremely flammable aerosol
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
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H272	May intensify fire; oxidizer
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H281	Contains refrigerated gas; may cause cryogenic burns or injury
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Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
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
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H320	Causes eye irritation
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H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
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H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
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. 104594-70-9 ] {[proInfo.proName]}

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[ 104594-70-9 ] Synthesis Path-Upstream 1~13

[ 104594-70-9 ] Synthesis Path-Downstream 1~20

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