[(E)-2,3-dimethyl-4-oxobut-2-enyl] benzoate | 155389-66-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(E)-2,3-dimethyl-4-oxobut-2-enyl] benzoate
• CAS: 155389-66-5
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: ATRWOKKPSLJGON-ZHACJKMWSA-N

物化性质

• 沸点：
  364.8±25.0 °C(predicted)
• 密度：
  1.089±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyltitanium triisopropoxide 、 [(E)-2,3-dimethyl-4-oxobut-2-enyl] benzoate 以21%的产率得到[(E)-4-hydroxy-2,3-dimethylhex-2-enyl] benzoate
  参考文献：
  名称：

  Stereoselective Synthesis of the Bis-tetrahydrofuran Fragment (C-1-C-9) of Asteltoxin

  摘要：

  An 18-step synthesis of the chiral bis-tetrahydrofuran fragment 2 of asteltoxin 1 is described. This synthesis proceeds under practically complete substrate stereocontrol, starting with compound 5a. From there the chirality centers of 2 are generated with >95% ds each by using a sequence of Claisen rearrangement, chelate Cram Grignard addition, and osmylation reactions. The current synthesis affords 2 in racemic form. The key intermediate 8 was also synthesized with ee > 96%, which should provide access to 2 in both enantiomeric forms.

  DOI：

  10.1021/jo00084a039
• 作为产物：
  描述：

  Benzoic acid (E)-4-hydroxy-2,3-dimethyl-but-2-enyl ester 在 草酰氯 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 生成 [(E)-2,3-dimethyl-4-oxobut-2-enyl] benzoate
  参考文献：
  名称：

  Stereoselective Synthesis of the Bis-tetrahydrofuran Fragment (C-1-C-9) of Asteltoxin

  摘要：

  An 18-step synthesis of the chiral bis-tetrahydrofuran fragment 2 of asteltoxin 1 is described. This synthesis proceeds under practically complete substrate stereocontrol, starting with compound 5a. From there the chirality centers of 2 are generated with >95% ds each by using a sequence of Claisen rearrangement, chelate Cram Grignard addition, and osmylation reactions. The current synthesis affords 2 in racemic form. The key intermediate 8 was also synthesized with ee > 96%, which should provide access to 2 in both enantiomeric forms.

  DOI：

  10.1021/jo00084a039

文献信息

• Stereoselective Synthesis of the Bis-tetrahydrofuran Fragment (C-1-C-9) of Asteltoxin
  作者：Johann Mulzer、Joerg-Torsten Mohr

  DOI：10.1021/jo00084a039

  日期：1994.3

  An 18-step synthesis of the chiral bis-tetrahydrofuran fragment 2 of asteltoxin 1 is described. This synthesis proceeds under practically complete substrate stereocontrol, starting with compound 5a. From there the chirality centers of 2 are generated with >95% ds each by using a sequence of Claisen rearrangement, chelate Cram Grignard addition, and osmylation reactions. The current synthesis affords 2 in racemic form. The key intermediate 8 was also synthesized with ee > 96%, which should provide access to 2 in both enantiomeric forms.