1-(t-butyldimethylsilyl)-3,3-bis-(2'-propenyl)-2-azetidinone | 1058693-02-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 1-(t-butyldimethylsilyl)-3,3-bis-(2'-propenyl)-2-azetidinone
• 英文别名: 3,3-diallyl-1-(tert-butyldimethylsilyl)azetidin-2-one
• CAS: 1058693-02-9
• 化学式: C₁₅H₂₇NOSi
• 分子量: 265.471
• InChiKey: RJKAMNVFENFDHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.31
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(t-butyldimethylsilyl)-3,3-bis-(2'-propenyl)-2-azetidinone 在 cesium fluoride 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以0.15 g的产率得到3,3-diallylazetidin-2-one
  参考文献：
  名称：

  Formation of Acridones by Ethylene Extrusion in the Reaction of Arynes with β-Lactams and Dihydroquinolinones

  摘要：

  N-Unsubstituted beta-lactams react with a molecule of aryne by insertion into the amide bond to form a 2,3-dihydroquinolin-4-one, which subsequently reacts with another molecule of aryne to form an acridone by extrusion of a molecule of ethylene. 2,3-Dihydroquinolin-4-ones react under the same reaction conditions to afford identical results. This is the first example of ethylene extrusion in aryne chemistry.

  DOI：

  10.1021/jo3011073
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 在 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 1-(t-butyldimethylsilyl)-3,3-bis-(2'-propenyl)-2-azetidinone
  参考文献：
  名称：

  Formation of Acridones by Ethylene Extrusion in the Reaction of Arynes with β-Lactams and Dihydroquinolinones

  摘要：

  N-Unsubstituted beta-lactams react with a molecule of aryne by insertion into the amide bond to form a 2,3-dihydroquinolin-4-one, which subsequently reacts with another molecule of aryne to form an acridone by extrusion of a molecule of ethylene. 2,3-Dihydroquinolin-4-ones react under the same reaction conditions to afford identical results. This is the first example of ethylene extrusion in aryne chemistry.

  DOI：

  10.1021/jo3011073

文献信息

• 3-Alkenyl-2-azetidinones as fatty acid amide hydrolase inhibitors
  作者：Allan Urbach、Giulio G. Muccioli、Eric Stern、Didier M. Lambert、Jacqueline Marchand-Brynaert

  DOI：10.1016/j.bmcl.2008.05.081

  日期：2008.7

  A series of novel 2-azetidinones (beta-lactams) bearing short alkenyl chains at C3 and N1 have been prepared and evaluated in vitro as inhibitors of human FAAH. Compound 9c (1-(4'-pentenoyl-3-(4'-pentenyl)2- azetidinone)) featured an IC(50) value of 4.5 mu M and a good selectivity for FAAH versus MGL. (C) 2008 Elsevier Ltd. All rights reserved.