Ethyl 2-chloro-2,3-epoxyheptanoate | 111055-65-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: Ethyl 2-chloro-2,3-epoxyheptanoate
• 英文别名: Oxiranecarboxylic acid, 3-butyl-2-chloro-, ethyl ester；ethyl 3-butyl-2-chlorooxirane-2-carboxylate
• CAS: 111055-65-3
• 化学式: C₉H₁₅ClO₃
• 分子量: 206.669
• InChiKey: DNOBYWMUTDQTAR-UHFFFAOYSA-N

物化性质

• 沸点：
  70-74 °C(Press: 3 Torr)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 2-chloro-2,3-epoxyheptanoate 在 aluminum oxide 、 sodium tetrahydroborate 、 Lipase PS (Amano) 作用下， 以 乙醇 、 异丙醚 、 xylene 为溶剂， 反应 3.17h， 生成 ethyl (2R,3R)-2-acetyloxy-3-chloroheptanoate
  参考文献：
  名称：

  Lipase-catalyzed kinetic resolution of 3-chloro-2-hydroxyalkanoates. Its application for the synthesis of (−)-disparlure

  摘要：

  Reduction of 3-chloro-2-oxoalkanoates 1 with NaBH4 gave predominantly syn-3-chloro-2-hydroxyalkanoates 2 (synlanti=91/9-99/1) in 50-97% yields. Resolution of syn-2 by lipase-catalyzed transesterification gave (2S,3S)-2 and (2R,3R)-2-acetoxy-3-chloroalkanoates (2R,3R)-3. Total synthesis of (-)-disparlure, the pheromone of the gypsy moth was established from (2S,3S)-2g via 4 steps in 34.9% overall yield. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(96)00529-0
• 作为产物：
  描述：

  正戊醛 、 二氯乙酸乙酯 在 sodium ethanolate 作用下， 以 乙醚 为溶剂， 以86%的产率得到Ethyl 2-chloro-2,3-epoxyheptanoate
  参考文献：
  名称：

  A Facile Synthesis of 3-Chloro-2-oxoalkanoatesviaThermal Rearrangement of 2-Chloro-2,3-epoxyalkanoates Promoted by Alumina

  摘要：

  描述了一种通过铝土矿促进的2-氯-2,3-环氧烷酸酯的热重排，便捷合成3-氯-2-氧烷酸酯的方法。

  DOI：

  10.1055/s-1987-27923

文献信息

• One‐Pot Substitution‐Rearrangement Reaction of 2‐Chloroglycidic Ester: Effective Protocol for the Preparation of 3‐Arylsulfenyl‐2‐keto Ester
  作者：Takuzo Komiyama、Yutaka Takaguchi、Sadao Tsuboi

  DOI：10.1080/00397910500374914

  日期：2006.1

  Abstract The one‐pot substitution‐rearrangement reaction of 2‐chloroglycidic ester is reported. Treatment of 2‐chloroglycidic ester with sodium arylthiolate at room temperature results in the formation of 3‐arylsulfenyl‐2‐keto ester in excellent to good yields.

  摘要 报道了2-氯缩水甘油酯的一锅取代重排反应。在室温下用芳基硫醇钠处理 2-氯缩水甘油酯导致 3-芳基硫基-2-酮酯的形成，产率非常好。
• A Facile Synthesis of 3-Chloro-2-oxoalkanoates<i>via</i>Thermal Rearrangement of 2-Chloro-2,3-epoxyalkanoates Promoted by Alumina
  作者：Sadao Tsuboi、Hiroyuki Furutani、Akira Takeda

  DOI：10.1055/s-1987-27923

  日期：——

  Convenient synthesis of 3-chloro-2-oxoalkanoates via the thermal rearrangement of 2-chloro-2,3-epoxyalkanoates promoted by alumina is described.

  描述了一种通过铝土矿促进的2-氯-2,3-环氧烷酸酯的热重排，便捷合成3-氯-2-氧烷酸酯的方法。
• Convenient Rearrangement Reaction of 2‐Chloroglycidic Esters by PPh₃: A New Synthetic Method of 3‐Chloro‐2‐keto Esters
  作者：Takuzo Komiyama、Yutaka Takaguchi、Sadao Tsuboi

  DOI：10.1080/00397910600764618

  日期：2006.9

  Abstract A convenient rearrangement reaction of 2‐chloroglycidic esters is reported. Treatment of 2‐chloroglycidic esters with PPh3 under refluxing condition results in the formation of 3‐chloro‐2‐keto esters in good to reasonable yields.

  摘要 报道了一种方便的 2-氯缩水甘油酯重排反应。在回流条件下用 PPh3 处理 2-氯缩水甘油酯导致 3-氯-2-酮酯以良好到合理的产率形成。
• TSUBOI SADAO; FURUTANI HIROYUKI; TAKEDA AKIRA, SYNTHESIS,(1987) N 3, 292-293
  作者：TSUBOI SADAO、 FURUTANI HIROYUKI、 TAKEDA AKIRA

  DOI：——

  日期：——
• Lipase-catalyzed kinetic resolution of 3-chloro-2-hydroxyalkanoates. Its application for the synthesis of (−)-disparlure
  作者：Sadao Tsuboi、Nobuyuki Yamafuji、Masanori Utaka

  DOI：10.1016/s0957-4166(96)00529-0

  日期：1997.2

  Reduction of 3-chloro-2-oxoalkanoates 1 with NaBH4 gave predominantly syn-3-chloro-2-hydroxyalkanoates 2 (synlanti=91/9-99/1) in 50-97% yields. Resolution of syn-2 by lipase-catalyzed transesterification gave (2S,3S)-2 and (2R,3R)-2-acetoxy-3-chloroalkanoates (2R,3R)-3. Total synthesis of (-)-disparlure, the pheromone of the gypsy moth was established from (2S,3S)-2g via 4 steps in 34.9% overall yield. (C) 1997 Elsevier Science Ltd. All rights reserved.