(E)-7-[2-(3-Phenylsulfanyl-prop-1-ynyl)-phenyl]-hept-2-en-6-ynoic acid methyl ester

Base Information

Chemical Name:(E)-7-[2-(3-Phenylsulfanyl-prop-1-ynyl)-phenyl]-hept-2-en-6-ynoic acid methyl ester
CAS No.:185903-53-1
Molecular Formula:C₂₃H₂₀O₂S
Molecular Weight:360.477
Hs Code.:

Synonyms:(E)-7-[2-(3-Phenylsulfanyl-prop-1-ynyl)-phenyl]-hept-2-en-6-ynoic acid methyl ester

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Chemical Property of (E)-7-[2-(3-Phenylsulfanyl-prop-1-ynyl)-phenyl]-hept-2-en-6-ynoic acid methyl ester

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Technology Process of (E)-7-[2-(3-Phenylsulfanyl-prop-1-ynyl)-phenyl]-hept-2-en-6-ynoic acid methyl ester

There total 7 articles about (E)-7-[2-(3-Phenylsulfanyl-prop-1-ynyl)-phenyl]-hept-2-en-6-ynoic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 615-42-9
1,2-Diiodobenzene

: 185903-53-1
(E)-7-[2-(3-Phenylsulfanyl-prop-1-ynyl)-phenyl]-hept-2-en-6-ynoic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) Pd(PPh₃)2Cl₂, Et₃N, CuI / 1.) THF, 20 min, 2.) THF, room temperature, overnight

2: 1.) Et₃N, Pd(PPh₃)2Cl₂, CuI / 1.) THF, 2.) THF

3: 94 percent / Et₃N / CH₂Cl₂ / Ambient temperature

4: 97 percent / aq. NaOH / tetrahydrofuran / 1 h

5: 91 percent / aq. AcOH / tetrahydrofuran / Ambient temperature

6: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 25 min, 2.) CH₂Cl₂, -78 deg C, 1 h

7: 1.) DBU, LiCl / 1.) MeCN, room temperature, 15 min, 2.) MeCN, 1 min

With bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; copper(l) iodide; oxalyl dichloride; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo961049j

Reference yield:

: 156093-12-8
3-<2-(5-((tert-butyldimethylsilyl)oxy)-1-pentynyl)phenyl>-2-propyn-1-ol

: 185903-53-1
(E)-7-[2-(3-Phenylsulfanyl-prop-1-ynyl)-phenyl]-hept-2-en-6-ynoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 94 percent / Et₃N / CH₂Cl₂ / Ambient temperature

2: 97 percent / aq. NaOH / tetrahydrofuran / 1 h

3: 91 percent / aq. AcOH / tetrahydrofuran / Ambient temperature

4: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 25 min, 2.) CH₂Cl₂, -78 deg C, 1 h

5: 1.) DBU, LiCl / 1.) MeCN, room temperature, 15 min, 2.) MeCN, 1 min

With sodium hydroxide; oxalyl dichloride; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo961049j

Reference yield:

: 176384-79-5
1-(3-hydroxy-1-propynyl)-2-iodobenzene

: 185903-53-1
(E)-7-[2-(3-Phenylsulfanyl-prop-1-ynyl)-phenyl]-hept-2-en-6-ynoic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) Et₃N, Pd(PPh₃)2Cl₂, CuI / 1.) THF, 2.) THF

2: 94 percent / Et₃N / CH₂Cl₂ / Ambient temperature

3: 97 percent / aq. NaOH / tetrahydrofuran / 1 h

4: 91 percent / aq. AcOH / tetrahydrofuran / Ambient temperature

5: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 25 min, 2.) CH₂Cl₂, -78 deg C, 1 h

6: 1.) DBU, LiCl / 1.) MeCN, room temperature, 15 min, 2.) MeCN, 1 min

With bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; copper(l) iodide; oxalyl dichloride; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo961049j