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

Base Information

Chemical Name:3-{(2Z)-2-[(2E)-4-benzyloxy-1-bromo-2-butenylidene]cyclohexyl}-N-hydroxypropanamide
CAS No.:264134-88-5
Molecular Formula:C₂₀H₂₆BrNO₃
Molecular Weight:408.335
Hs Code.:

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

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

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

There total 13 articles about 3-{(2Z)-2-[(2E)-4-benzyloxy-1-bromo-2-butenylidene]cyclohexyl}-N-hydroxypropanamide 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: 79.0%

: 273936-82-6
methyl 3-{(2Z)-2-[(2E)-4-benzyloxy-1-bromo-2-butenylidene]cyclohexyl}propanoate

: 264134-88-5
3-{(2Z)-2-[(2E)-4-benzyloxy-1-bromo-2-butenylidene]cyclohexyl}-N-hydroxypropanamide

Guidance literature:: With potassium hydroxide; hydroxylamine hydrochloride; In methanol; at 0 ℃; for 2h;
DOI:10.1021/ja9939284

Reference yield:

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

: 264134-88-5
3-{(2Z)-2-[(2E)-4-benzyloxy-1-bromo-2-butenylidene]cyclohexyl}-N-hydroxypropanamide

Guidance literature:: Multi-step reaction with 7 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

6: 83 percent / diethyl ether / 0.5 h / 0 °C

7: 79 percent / NH₂OH*HCl; KOH / methanol / 2 h / 0 °C

With potassium hydroxide; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; hydroxylamine hydrochloride; tetra(n-butyl)ammonium hydrogensulfate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; tert-butyl alcohol; In methanol; diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol; benzene; 1: Reduction / 2: Etherification / 3: Hydrolysis / 4: Swern oxidation / 5: Oxidation / 6: Esterification / 7: amidation;
DOI:10.1021/ja9939284

Reference yield:

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

: 264134-88-5
3-{(2Z)-2-[(2E)-4-benzyloxy-1-bromo-2-butenylidene]cyclohexyl}-N-hydroxypropanamide

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent / NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 2 h / 20 °C

2: 83 percent / diethyl ether / 0.5 h / 0 °C

3: 79 percent / NH₂OH*HCl; KOH / methanol / 2 h / 0 °C

With potassium hydroxide; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; hydroxylamine hydrochloride; In methanol; diethyl ether; water; tert-butyl alcohol; 1: Oxidation / 2: Esterification / 3: amidation;
DOI:10.1021/ja9939284