(4S,2'S,3'R)-N(3)-(2'-vinyl-3'-hydroxybutanoyl)-4-isopropyl-5,5-dimethyl-oxazolidin-2-one | 1190930-08-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S,2'S,3'R)-N(3)-(2'-vinyl-3'-hydroxybutanoyl)-4-isopropyl-5,5-dimethyl-oxazolidin-2-one
• 英文别名: (4S)-3-[(2S)-2-[(1R)-1-hydroxyethyl]but-3-enoyl]-5,5-dimethyl-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 1190930-08-5
• 化学式: C₁₄H₂₃NO₄
• 分子量: 269.341
• InChiKey: ZNOZJVAOSKBSGH-VWYCJHECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,2'S,3'R)-N(3)-(2'-vinyl-3'-hydroxybutanoyl)-4-isopropyl-5,5-dimethyl-oxazolidin-2-one 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以44%的产率得到(4S)-4-异丙基-5,5-二甲基-1,3-恶唑烷-2-酮
  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
• 作为产物：
  描述：

  (S,E)-3-(but-2-enoyl)-4-isopropyl-5,5-dimethyloxazolidin-2-one 、 乙醛 在 三氟甲磺酸二丁硼 、 三乙胺 、 水 、 双氧水 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 1.0h， 以65%的产率得到(4S,2'S,3'R)-N(3)-(2'-vinyl-3'-hydroxybutanoyl)-4-isopropyl-5,5-dimethyl-oxazolidin-2-one
  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