2-(1-hydroxy-2-methylpropyl)-but-3-enoic acid

• 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: 2-(1-hydroxy-2-methylpropyl)-but-3-enoic acid
• 英文别名: (2S,3R)-2-ethenyl-3-hydroxy-4-methylpentanoic acid
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: RNLHTAOFGPEIGV-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.89
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  57.53
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  (4S,2'S,3'R)-N(3)-(2'-vinyl-3'-hydroxy-4'-methylpentanoyl)-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89%的产率得到2-(1-hydroxy-2-methylpropyl)-but-3-enoic 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

• Exclusive <i>α</i>-Coupling in the Aldol Reaction of Unsaturated Trimethylsilyl Esters: An Efficient and Practical Direct Synthesis of Unsaturated <i>β</i>-Hydroxy Acids
  作者：Moncef Bellassoued、Jérôme Grugier、Nathalie Lensen、Audrey Catheline

  DOI：10.1021/jo020128u

  日期：2002.8.1

  give exclusively the alpha-condensation products in excellent yields. The unsaturated beta-hydroxy acids thus obtained were directly identified, and the usual conversion into their methyl esters with diazomethane was not necessary. Unsaturated ketones underwent Michael reaction through alpha-addition leading to the unsaturated 5-oxo acids.

  丁烯酸三甲基甲硅烷基酯和丁烯酸3-甲基丁酯的烯醇锂与醛和饱和或芳香族酮在-70℃下反应，以优异的产率仅得到α缩合产物。由此获得的不饱和β-羟基酸被直接鉴定，并且不需要用重氮甲烷通常转化为它们的甲酯。不饱和酮通过α加成反应发生迈克尔反应，从而导致不饱和5-氧代酸。
• Synthesis of α-alkenyl-β-hydroxy adducts by α-addition of unprotected 4-bromocrotonic acid and amides with aldehydes and ketones by chromium(II)-mediated reactions
  作者：Ludger A. Wessjohann、Harry Wild、Leonildo A. Ferreira、Henri S. Schrekker

  DOI：10.1002/aoc.3488

  日期：2016.8

  The regioselective and diastereoselective chromium(II)‐mediated reactions of 4‐bromocrotonic acid or amides with aldehydes and ketones can proceed without the need to protect protic sites to generate the respective α‐alkenyl‐β‐hydroxy adducts, i.e. formally the addition of the α‐anion of a carboxylic acid or amide to an oxo‐compound is featured. Copyright © 2016 John Wiley & Sons, Ltd.

  可以进行4-溴巴豆酸或酰胺与醛和酮的区域选择性和非对映选择性铬（II）介导的反应，而无需保护质子位点以生成相应的α-烯基-β-羟基加合物，即正式添加具有羧酸或酰胺的α-阴离子与羰基化合物的特征。版权所有©2016 John Wiley＆Sons，Ltd.
• 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.