(+)-2Z,4E-5-[(1S)-3-bromo-1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl]-3-methyl-2,4-pentadienoic acid

Base Information

Chemical Name:(+)-2Z,4E-5-[(1S)-3-bromo-1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl]-3-methyl-2,4-pentadienoic acid
CAS No.:260963-93-7
Molecular Formula:C₁₅H₁₉BrO₄
Molecular Weight:343.217
Hs Code.:

Synonyms:(+)-2Z,4E-5-[(1S)-3-bromo-1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl]-3-methyl-2,4-pentadienoic acid

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Chemical Property of (+)-2Z,4E-5-[(1S)-3-bromo-1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl]-3-methyl-2,4-pentadienoic acid

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Technology Process of (+)-2Z,4E-5-[(1S)-3-bromo-1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl]-3-methyl-2,4-pentadienoic acid

There total 2 articles about (+)-2Z,4E-5-[(1S)-3-bromo-1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl]-3-methyl-2,4-pentadienoic 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: 23.0%

: 260963-97-1
(+)-2Z,4E-5-[(1S,2S,3R)-3-bromo-1,2-dihydroxy-2,6,6-trimethyl-4-oxocyclohexan-1-yl]-3-methyl-2,4-pentadienoic acid

: 260963-93-7
(+)-2Z,4E-5-[(1S)-3-bromo-1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl]-3-methyl-2,4-pentadienoic acid

Guidance literature:: With hydrogen bromide; In methanol; at 20 ℃; for 3.7h;
DOI:10.1016/S0031-9422(99)00444-6

Reference yield:

: 164854-64-2
(+)-2',3'-dihydro-2'α,3'α-epoxyabscisic acid

: 260963-93-7
(+)-2Z,4E-5-[(1S)-3-bromo-1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl]-3-methyl-2,4-pentadienoic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 36 percent / aq. HBr / methanol / 1.3 h / 18 °C

2: 23 percent / aq. HBr / methanol / 3.7 h / 20 °C

With hydrogen bromide; In methanol; 1: Addition / 2: Dehydration;
DOI:10.1016/S0031-9422(99)00444-6

Reference yield:

: 260963-93-7
(+)-2Z,4E-5-[(1S)-3-bromo-1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl]-3-methyl-2,4-pentadienoic acid

: (2Z,4E)‐5‐((S)‐1‐hydroxy‐3‐iodo‐2,6,6‐trimethyl‐4‐oxocyclohex‐2‐en‐1‐yl)‐3‐methylpenta‐2,4‐dienoic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 57 mg

2: 44 percent / KI; CuI / hexamethylphosphoric acid triamide / 0.7 h / 150 °C

3: 77 percent / porcine liver esterase (EC 3.1.1.1, 2000 units) / methanol; aq. phosphate buffer / 5.8 h / 30 °C / pH 8.0 / Enzymatic reaction

With copper(l) iodide; porcine liver esterase (EC 3.1.1.1, 2000 units); potassium iodide; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; phosphate buffer; 1: Methylation / 2: Substitution / 3: Hydrolysis;
DOI:10.1016/S0031-9422(99)00444-6