3-{(2Z)-2-[(2E)-4-benzyloxy-1-bromo-2-butenylidene]cyclohexyl}propanoic acid

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Chemical Name:3-{(2Z)-2-[(2E)-4-benzyloxy-1-bromo-2-butenylidene]cyclohexyl}propanoic acid
CAS No.:264134-87-4
Molecular Formula:C₂₀H₂₅BrO₃
Molecular Weight:393.321
Hs Code.:

Synonyms:3-{(2Z)-2-[(2E)-4-benzyloxy-1-bromo-2-butenylidene]cyclohexyl}propanoic acid

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Chemical Property of 3-{(2Z)-2-[(2E)-4-benzyloxy-1-bromo-2-butenylidene]cyclohexyl}propanoic acid

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Technology Process of 3-{(2Z)-2-[(2E)-4-benzyloxy-1-bromo-2-butenylidene]cyclohexyl}propanoic acid

There total 11 articles about 3-{(2Z)-2-[(2E)-4-benzyloxy-1-bromo-2-butenylidene]cyclohexyl}propanoic acid 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: 80.0%

: 273936-81-5
3-{(2Z)-2-[(2E)-4-benzyloxy-1-bromo-2-butenylidene]cyclohexyl}propanal

: 264134-87-4
3-{(2Z)-2-[(2E)-4-benzyloxy-1-bromo-2-butenylidene]cyclohexyl}propanoic acid

Guidance literature:: With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 20 ℃; for 2h;
DOI:10.1021/ja9939284

Reference yield:

: 273936-78-0
ethyl (2E)-4-bromo-4-{2-[3-(methoxymethyloxy)propyl]cyclohexylidene}-2-butenoate

: 264134-87-4
3-{(2Z)-2-[(2E)-4-benzyloxy-1-bromo-2-butenylidene]cyclohexyl}propanoic acid

Guidance literature:: Multi-step reaction with 5 steps

1: 50 percent / DIBALH / CH₂Cl₂; hexane / 2 h / 0 °C

2: 89 percent / Bu₄N*HSO₄; aq. NaOH / benzene / 24 h / 20 °C

3: 84 percent / PPTS; t-BuOH / 8 h / 80 °C

4: 94 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

5: 80 percent / NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 2 h / 20 °C

With sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; tetra(n-butyl)ammonium hydrogensulfate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; tert-butyl alcohol; In hexane; dichloromethane; water; tert-butyl alcohol; benzene; 1: Reduction / 2: Etherification / 3: Hydrolysis / 4: Swern oxidation / 5: Oxidation;
DOI:10.1021/ja9939284

Reference yield:

: 264134-86-3
{[((2E,4Z)-4-bromo-4-{2-[3-(methoxymethyloxy)propyl]cyclohexylidene}-2-butenyl)oxy]methyl}benzene

: 264134-87-4
3-{(2Z)-2-[(2E)-4-benzyloxy-1-bromo-2-butenylidene]cyclohexyl}propanoic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 84 percent / PPTS; t-BuOH / 8 h / 80 °C

2: 94 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3: 80 percent / NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 2 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; tert-butyl alcohol; In dichloromethane; water; tert-butyl alcohol; 1: Hydrolysis / 2: Swern oxidation / 3: Oxidation;
DOI:10.1021/ja9939284