methyl (S)-2-((R)-1-hydroxy-2-phenylethyl)but-3-enoate | 1190930-35-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl (S)-2-((R)-1-hydroxy-2-phenylethyl)but-3-enoate
• CAS: 1190930-35-8
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: JQHOTCYQKVPPCV-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.57
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  甲醇 、 (4S,2'S,3'R)-N(3)-(2'-vinyl-3'-hydroxy-4'-phenylbutanoyl)-4-isopropyl-5,5-dimethyl-oxazolidin-2-one 在 正丁基锂 、 水 、 氯化铵 作用下， 以 甲醇 、 正戊烷 为溶剂， 生成 (3R)-2-ethylidene-3-hydroxy-4-phenylbutanoate 、 methyl (S)-2-((R)-1-hydroxy-2-phenylethyl)but-3-enoate
  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