(2S,3R)-2-vinyl-3-hydroxybutanoic acid | 1190930-19-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3R)-2-vinyl-3-hydroxybutanoic acid
• 英文别名: (2S)-2-[(1R)-1-hydroxyethyl]but-3-enoic acid
• CAS: 1190930-19-8
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: DQEHALOFBSCPIB-UHNVWZDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (4S,2'S,3'R)-N(3)-(2'-vinyl-3'-hydroxybutanoyl)-4-isopropyl-5,5-dimethyl-oxazolidin-2-one 在 水 、 双氧水 、 lithium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以42%的产率得到(2S,3R)-2-vinyl-3-hydroxybutanoic acid
  参考文献：
  名称：

  The dienolate aldol reaction of (E)-N-crotonoyl C(4)-isopropyl SuperQuat: asymmetric synthesis of α-vinyl-β-hydroxycarboxylic acid derivatives and conversion to α-ethylidene-β-hydroxyesters (β-substituted Baylis–Hillman products)

  摘要：

  The synthesis of alpha-vinyl-beta-hydroxyesters and alpha-ethlylidene-beta-hydroxyesters (beta-substituted Baylis-Hillman products) Via the dienolate aldol reaction of (E)-N-crotonoyl C(4)-isopropyl SuperQuat is described. High levels of syn-diastereoselectivity (up to >98% de) are observed for the dienolate aldol reaction with boron enolates, generated either directly with Bu2BOTf or by transmetalation of the potassium enolate with B-bromocatecholborane. Cleavage of the resultant syn-aldol products from the auxiliary gives alpha-vinyl-beta-hydroxyesters in >98% de and >98% ee. Subsequent isomerisation of the double bond into conjugation provides alpha-ethylidene-beta-hydroxyesters (beta-substituted Baylis-Hillman products) in high diastereo- and enantiopurity (>= 91:9 |(E):(Z)| and >98% ee). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.07.004

文献信息

• Antibacterial agents
  申请人：The University of Washington

  公开号：EP2295402B1

  公开（公告）日：2015-08-12
• The dienolate aldol reaction of (E)-N-crotonoyl C(4)-isopropyl SuperQuat: asymmetric synthesis of α-vinyl-β-hydroxycarboxylic acid derivatives and conversion to α-ethylidene-β-hydroxyesters (β-substituted Baylis–Hillman products)
  作者：Stephen G. Davies、Dirk L. Elend、Simon Jones、Paul M. Roberts、Edward D. Savory、Andrew D. Smith、James E. Thomson

  DOI：10.1016/j.tet.2009.07.004

  日期：2009.9

  The synthesis of alpha-vinyl-beta-hydroxyesters and alpha-ethlylidene-beta-hydroxyesters (beta-substituted Baylis-Hillman products) Via the dienolate aldol reaction of (E)-N-crotonoyl C(4)-isopropyl SuperQuat is described. High levels of syn-diastereoselectivity (up to >98% de) are observed for the dienolate aldol reaction with boron enolates, generated either directly with Bu2BOTf or by transmetalation of the potassium enolate with B-bromocatecholborane. Cleavage of the resultant syn-aldol products from the auxiliary gives alpha-vinyl-beta-hydroxyesters in >98% de and >98% ee. Subsequent isomerisation of the double bond into conjugation provides alpha-ethylidene-beta-hydroxyesters (beta-substituted Baylis-Hillman products) in high diastereo- and enantiopurity (>= 91:9 |(E):(Z)| and >98% ee). (C) 2009 Elsevier Ltd. All rights reserved.