(S)-2-((2-methylthiazol-4-yl)methyl)hexa-1,5-dien-3-yl acetate | 1156508-47-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S)-2-((2-methylthiazol-4-yl)methyl)hexa-1,5-dien-3-yl acetate
• 英文别名: [(3S)-2-[(2-methyl-1,3-thiazol-4-yl)methyl]hexa-1,5-dien-3-yl] acetate
• CAS: 1156508-47-2
• 化学式: C₁₃H₁₇NO₂S
• 分子量: 251.349
• InChiKey: MRMLPWZAHAUGLI-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-((2-methylthiazol-4-yl)methyl)hexa-1,5-dien-3-yl acetate 在 potassium tert-butylate 、 水 作用下， 以 叔丁醇 为溶剂， 反应 0.75h， 以80%的产率得到(S,E)-2-methyl-1-(2-methylthiazol-4-yl)hexa-1,5-dien-3-ol
  参考文献：
  名称：

  A cyclopropanol approach to the synthesis of both enantiomers of the C13–C21 fragment of epothilones

  摘要：

  Efficient syntheses of both enantiomers of the C13-C21 fragment of epothilone molecules have been performed by use of enantiomeric oxiranyl-substituted cyclopropylsulfonates as key intermediates. The latter were obtained by the cyclopropanation of easily available (R)-methyl 2,3-O-isopropylideneglycerate and subsequent manipulation of the functional groups. Asymmetric allylation of 1-formylcyclopropyl pivalate led to an alternative precursor of the target compounds with moderate enantioselectivity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.02.003
• 作为产物：
  描述：

  (S)-2-(bromomethyl)hexa-1,5-dien-3-yl acetate 、 4-溴-2-甲基噻唑 在 正丁基锂 、 magnesium bromide 、 copper(l) iodide 作用下， 以 乙醚 、 正己烷 、 四氢呋喃 为溶剂， 反应 3.08h， 以85%的产率得到(S)-2-((2-methylthiazol-4-yl)methyl)hexa-1,5-dien-3-yl acetate
  参考文献：
  名称：

  A cyclopropanol approach to the synthesis of both enantiomers of the C13–C21 fragment of epothilones

  摘要：

  Efficient syntheses of both enantiomers of the C13-C21 fragment of epothilone molecules have been performed by use of enantiomeric oxiranyl-substituted cyclopropylsulfonates as key intermediates. The latter were obtained by the cyclopropanation of easily available (R)-methyl 2,3-O-isopropylideneglycerate and subsequent manipulation of the functional groups. Asymmetric allylation of 1-formylcyclopropyl pivalate led to an alternative precursor of the target compounds with moderate enantioselectivity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.02.003