ethyl (E)-3<(S)-1,3-dioxolan-4-yl>acrylate | 144602-91-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (E)-3<(S)-1,3-dioxolan-4-yl>acrylate
• 英文别名: ethyl (E)-3-[(4S)-1,3-dioxolan-4-yl]prop-2-enoate
• CAS: 144602-91-5
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: NTCLGPTVCGWEJA-SDLBARTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (E)-3<(S)-1,3-dioxolan-4-yl>acrylate 、 ethyl ([1R,2E,4R]-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylideneamino)acetate 在 叔丁醇 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 生成 diethyl N-<(1R,4R)-2-bornylidene>-3-<(S)-1,3-dioxolan-4-yl>-(2R,3R)-glutamate
  参考文献：
  名称：

  Double chiral induction in ul-selective Michael additions of metal enolates of N-bornylideneglycinates to (E)-4,5-dioxy-2-pentenoates. Exclusive ul,lk-1,2-chiral induction leading to l,u-Michael adducts

  摘要：

  ul-Selective Michael additions of metal enolates of ethyl N-[(1R,4R)-bornylidene]glycinate to optically pure (E)-4,5-dioxy-2-pentenoates, such as ethyl (E)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propenoate, ethyl (E)-3-(1,3-dioxolan-4-yl)propenoate, and ethyl (E)-4,5-diacetoxy-2-pentenoate, proceed through ul,lk-1,2-induction to provide pure enantiomers of 4-substituted 2-oxopyrrolidine-5-carboxylates as single diastereomers. Exclusive ul,lk-1,2-induction is achieved by use of the racemic enolates. Origin of such high stereocontrol is discussed by Kozikowski's antiperiplanar transition model.

  DOI：

  10.1021/jo00068a016
• 作为产物：
  描述：

  (S)-(+)-3-(2,2-二甲基-1,3-二氧戊环-4-基)-反式-丙酸乙酯 在 N-溴代丁二酰亚胺(NBS) 、 Amberlite IR 120 作用下， 反应 23.0h， 生成 ethyl (E)-3<(S)-1,3-dioxolan-4-yl>acrylate
  参考文献：
  名称：

  硅中心自由基向α-手性烯烃的立体选择性加成：Felkin-Anh立体电子控制。

  摘要：

  通过将大体积且亲核的硅中心自由基（TMS）3 Si·分子间添加到手性和构象柔性的烯烃中，可以实现完全的立体控制。通过X射线分析确定了观察到的立体选择性，并根据空间和Felkin-Anh立体电子控制进行了合理化。

  DOI：

  10.1016/s0040-4039(00)61131-0

文献信息

• Stereoselective additions of silicon centered radical to α-chiral olefins: A Felkin-Anh stereoelectronic control.
  作者：William Smadja、Mohamed Zahouily、Max Malacria

  DOI：10.1016/s0040-4039(00)61131-0

  日期：1992.9

  A complete stereocontrol has been achieved by intermolecular addition of the bulky and nucleophilic silicon centered radical (TMS)3Si· to a chiral and conformationally flexible olefin. The stereoselectivity observed has been established by X-ray analysis and rationalized in terms of steric and Felkin-Anh stereoelectronic controls.

  通过将大体积且亲核的硅中心自由基（TMS）3 Si·分子间添加到手性和构象柔性的烯烃中，可以实现完全的立体控制。通过X射线分析确定了观察到的立体选择性，并根据空间和Felkin-Anh立体电子控制进行了合理化。
• Double chiral induction in ul-selective Michael additions of metal enolates of N-bornylideneglycinates to (E)-4,5-dioxy-2-pentenoates. Exclusive ul,lk-1,2-chiral induction leading to l,u-Michael adducts
  作者：Akira Tatsukawa、Masashi Dan、Mika Ohbatake、Keiko Kawatake、Tomohiro Fukata、Eiji Wada、Shuji Kanemasa、Shoichi Kakei

  DOI：10.1021/jo00068a016

  日期：1993.7

  ul-Selective Michael additions of metal enolates of ethyl N-[(1R,4R)-bornylidene]glycinate to optically pure (E)-4,5-dioxy-2-pentenoates, such as ethyl (E)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)propenoate, ethyl (E)-3-(1,3-dioxolan-4-yl)propenoate, and ethyl (E)-4,5-diacetoxy-2-pentenoate, proceed through ul,lk-1,2-induction to provide pure enantiomers of 4-substituted 2-oxopyrrolidine-5-carboxylates as single diastereomers. Exclusive ul,lk-1,2-induction is achieved by use of the racemic enolates. Origin of such high stereocontrol is discussed by Kozikowski's antiperiplanar transition model.