(+)-(S)-hex-1-en-3-yl benzoate

• 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: (+)-(S)-hex-1-en-3-yl benzoate
• 英文别名: [(3S)-hex-1-en-3-yl] benzoate
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: PWEVLLZPVANVOL-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯甲酸 、 (Z)-2-hexenyl trichloroacetimidate 在 (-)-(S)-COP-OAc 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以100%的产率得到(+)-(S)-hex-1-en-3-yl benzoate
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of Chiral Allylic Esters

  摘要：

  Trichloroacetimidate derivatives of prochiral (Z)-2-alken-1-ols react at room temperature with carboxylic acids to give chiral 3-acyloxy-1-alkenes in high enantiopurity in the presence of di-mu-acetatobis[(eta5-(S)-(pR)-2-(2'-(4'-methylethyl)oxazolinyl)cyclopentadienyl,1-C,3'-N)(eta4-tetraphenylcyclobutadiene)cobalt]dipalladium (COP-OAc) or its enantiomer. This reaction has broad scope, proceeds with predictable high stereoinduction, is accomplished at room temperature using high substrate concentrations and low catalyst loadings, and likely proceeds by a novel mechanism.

  DOI：

  10.1021/ja0425583

文献信息

• Copper-catalyzed enantioselective allylic oxidation of acyclic olefins
  作者：Bo Zhang、Shou-Fei Zhu、Qi-Lin Zhou

  DOI：10.1016/j.tetlet.2013.03.046

  日期：2013.5

  copper-catalyzed asymmetric allylic oxidation of acyclic olefins has been developed. By using the complexes of copper and chiral spiro bisoxazoline ligands as catalysts, the oxidation of various acyclic olefins was accomplished with excellent regioselectivity (>20:1 in most cases) and up to 67% ee under mild reaction conditions, which represents one of the best results for the enantioselective allylic oxidation

  已经开发了铜催化的无环烯烃的不对称烯丙基氧化。通过使用铜和手性螺双恶唑啉配体的配合物作为催化剂，在温和的反应条件下，以优异的区域选择性（大多数情况下> 20：1）和高达67％ee的氧化完成了各种无环烯烃的氧化，这是其中的一种。无环烯烃的对映选择性烯丙基氧化的最佳结果。
• Kanbayashi, Naoya; Onitsuka, Kiyotaka, Journal of the American Chemical Society, 2010, vol. 132, p. 1206 - 1207
  作者：Kanbayashi, Naoya、Onitsuka, Kiyotaka

  DOI：——

  日期：——
• Catalytic Asymmetric Synthesis of Chiral Allylic Esters
  作者：Stefan F. Kirsch、Larry E. Overman

  DOI：10.1021/ja0425583

  日期：2005.3.9

  Trichloroacetimidate derivatives of prochiral (Z)-2-alken-1-ols react at room temperature with carboxylic acids to give chiral 3-acyloxy-1-alkenes in high enantiopurity in the presence of di-mu-acetatobis[(eta5-(S)-(pR)-2-(2'-(4'-methylethyl)oxazolinyl)cyclopentadienyl,1-C,3'-N)(eta4-tetraphenylcyclobutadiene)cobalt]dipalladium (COP-OAc) or its enantiomer. This reaction has broad scope, proceeds with predictable high stereoinduction, is accomplished at room temperature using high substrate concentrations and low catalyst loadings, and likely proceeds by a novel mechanism.