(R)-2-BENZYLBUT-3-ENOIC ACID

Base Information

• Chemical Name: (R)-2-BENZYLBUT-3-ENOIC ACID
• CAS No.: 183509-48-0
• Molecular Formula: C11H12O2
• Molecular Weight: 176.215
• Mol file: 183509-48-0.mol

Synonyms:(R)-2-BENZYLBUT-3-ENOIC ACID

Chemical Property of (R)-2-BENZYLBUT-3-ENOIC ACID

Chemical Property:

• PSA: 37.30000
• LogP: 2.11590

Purity/Quality:

99%min ^*data from raw suppliers

(R)-2-BENZYLBUT-3-ENOICACID 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (R)-2-BENZYLBUT-3-ENOIC ACID

There total 4 articles about (R)-2-BENZYLBUT-3-ENOIC 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: 90.0%

N-[(2R)-2-benzyl-3-butenoyl]-(1S)-2,10-camphorsultam (127392-99-8) → (R)-(-)-2-benzylbut-3-enoic acid (183509-48-0)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 0 - 20 ℃;

DOI:10.1016/S0040-4020(02)00795-0

Reference yield:

2-benzylbut-3-enenitrile (110036-21-0) → (S)-(+)-2-benzylbut-3-enamide + (R)-(-)-2-benzylbut-3-enamide + (S)-(+)-2-benzylbut-3-enoic acid + (R)-(-)-2-benzylbut-3-enoic acid (183509-48-0)

Guidance literature:

With potassium phosphate buffer; Rhodococcus erythropolis AJ₂₇₀ cells; In water; at 30 ℃; for 0.58h; pH=7.0; Title compound not separated from byproducts.;

DOI:10.1021/jo070581b

Reference yield:

benzyl bromide (100-39-0) → (R)-(-)-2-benzylbut-3-enoic acid (183509-48-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C

1.2: 62 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 16 h / -40 °C

2.1: 90 percent / LiOH*H₂O; aq. h2o2 / tetrahydrofuran; H₂O / 0 - 20 °C

With lithium hydroxide; dihydrogen peroxide; sodium hexamethyldisilazane; In tetrahydrofuran; water;

DOI:10.1016/S0040-4020(02)00795-0

upstream raw materials:

N-[(2R)-2-benzyl-3-butenoyl]-(1S)-2,10-camphorsultam

2-benzylbut-3-enenitrile

benzyl bromide

Downstream raw materials:

(2R)-2-benzyl-5-(trimethylsilyl)pent-3-enoic acid

(2R,1'R)-N-(1'-benzyl-prop-2'-enyl)-N-[(2,4-dimethoxyphenyl)methyl]-2-benzyl-but-3-enamide

(3R,6R)-N-[(2,4-dimethoxyphenyl)methyl]-3,6-dibenzyl-3,6-dihydro-2-pyridone

(3R,6R)-3,6-dibenzyl-2-ethoxy-3,6-dihydropyridine

Refernces

• 1、 Boucard, Valérie,Sauriat-Dorizon, Hélène,Guibé, Fran?ois. "An access to (Z)-ethylenic pseudodipeptides based on ring-closing metathesis". . p. 7275 - 7290. Retrieved 2007/10/03.