(2S,3E)-4-(4-bromophenyl)-3-buten-2-ol

Base Information

• Chemical Name: (2S,3E)-4-(4-bromophenyl)-3-buten-2-ol
• CAS No.: 690257-96-6
• Molecular Formula: C₁₀H₁₁BrO
• Molecular Weight: 227.101
• Mol file: 690257-96-6.mol

Synonyms:(2S,3E)-4-(4-bromophenyl)-3-buten-2-ol

Chemical Property of (2S,3E)-4-(4-bromophenyl)-3-buten-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3E)-4-(4-bromophenyl)-3-buten-2-ol

There total 11 articles about (2S,3E)-4-(4-bromophenyl)-3-buten-2-ol 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: 93.0%

(E)-4-(4-bromophenyl)but-3-ene-2-one (20511-04-0,3815-31-4) → (2S,3E)-4-(4-bromophenyl)-3-buten-2-ol (690257-96-6)

Guidance literature:

With C₅₂H₄₄Cl₂N₂OP₂Ru; potassium tert-butylate; hydrogen; In isopropyl alcohol; at 25 ℃; for 12h; under 7600.51 Torr; enantioselective reaction; Autoclave;

DOI:10.1021/ol501648a

Reference yield: 44.0%

vinyl acetate (108-05-4,9003-20-7) + (3E)-4-(4-bromophenyl)-3-buten-2-ol (32271-55-9) → (2S,3E)-4-(4-bromophenyl)-3-buten-2-ol (690257-96-6)

Guidance literature:

With Novozyme 435; for 24h; Inert atmosphere; Enzymatic reaction;

DOI:10.1055/s-0028-1088121

Reference yield:

(E)-4-(4-bromophenyl)but-3-ene-2-one (20511-04-0,3815-31-4) → (2S,3E)-4-(4-bromophenyl)-3-buten-2-ol (690257-96-6) + (2R,3E)-4-(4-bromophenyl)-3-buten-2-ol

Guidance literature:

(E)-4-(4-bromophenyl)but-3-ene-2-one; With C₅₁H₈₀N₄O₄; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; at 35 ℃; for 0.5h;

With potassium borohydride; In tetrahydrofuran; water; at 0 ℃; Overall yield = 99 %; enantioselective reaction;

DOI:10.1021/ol302430h

upstream raw materials:

methanol

(3E)-4-(4-bromophenyl)-3-buten-2-ol

C₁₀H₁₃BrOSSe

(E)-4-(4-bromophenyl)but-3-ene-2-one

Downstream raw materials:

(S)-[(S,E)-4-(4-bromophenyl)but-3-en-2-yl] 2-(tert-butoxycarbonylamino)propanoate

(βS)-4-bromo-N-(tert-butoxycarbonyl)-β-[(1E)-prop-1-en-1-yl]-L-phenylalanine

methyl (βS)-4-bromo-N-(tert-butoxycarbonyl)-β-[(1E)-prop-1-enyl]-L-phenylalaninate

(3S)-1-[(2S,3S,4E)-3-(4-bromophenyl)-2-(tert-butoxycarbonylamino)hex-4-enoyl]-3-fluoropyrrolidine

Refernces

• 1、 Albarrán-Velo, Jesús,Gotor-Fernández, Vicente,Lavandera, Iván. "One-pot two-step chemoenzymatic deracemization of allylic alcohols using laccases and alcohol dehydrogenases". . . Retrieved 2020/07/03.
• 2、 Chen, Xiangning,Zhou, Han,Zhang, Kunyu,Li, Jiawen,Huang, Hanmin. "Highly enantioselective hydrogenation of steric hindrance enones catalyzed by Ru complexes with chiral diamine and achiral phosphane". supporting information. p. 3912 - 3915. Retrieved 2014/08/18.