4-Aza-1-(2-bromoethyl)-4,6,6-triphenylspiro<2.3>hexan-5-one

• 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: 4-Aza-1-(2-bromoethyl)-4,6,6-triphenylspiro<2.3>hexan-5-one
• 英文别名: (2S,3S)-2-(2-bromoethyl)-4,6,6-triphenyl-4-azaspiro[2.3]hexan-5-one
• 化学式: C₂₅H₂₂BrNO
• 分子量: 432.36
• InChiKey: BOBXMJMYTDMJDZ-QPPBQGQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-溴-1-丁烯 、 1,7,8-triaza-6,6-dimethyl-5-oxa-2-oxo-1,3,3-triphenylspiro<3,4>oct-7-ene 以60%的产率得到4-Aza-1-(2-bromoethyl)-4,6,6-triphenylspiro<2.3>hexan-5-one
  参考文献：
  名称：

  Intermolecular Reactions of .beta.-Lactam-4-ylidenes with Alkenes, Alcohols, and Acetic Acid. Spiro-Fused .beta.-Lactam Cyclopropanes, 4-Alkoxy .beta.-Lactams, and a 4-Acetoxy .beta.-Lactam

  摘要：

  Thermolysis of spiro-fused beta-lactam oxadiazolines in the presence of alkenes gave spiro-fused beta-lactam cyclopropanes. The latter arise through a sequence of reactions beginning with 1,3-dipolar cycloreversion of an oxadiazoline to form N-2 and a short-lived carbonyl ylide. The latter fragments to acetone and a beta-lactam-4-ylidene, which adds to the alkene. Stereospecific additions to dimethyl fumarate and to dimethyl maleate are consistent with a concerted mechanism of cyclopropanation. The ylidenes also form cyclopropanes with alkenes that are not Michael accepters, including styrene and 4-bromo-1-butene. Thermolysis of beta-lactam oxadiazolines in the presence of hydroxylic compounds led to capture of beta-lactam-4-ylidenes by OH insertion, essentially in quantitative yields, as expected for reaction of singlet beta-lactam-4-ylidenes.

  DOI：

  10.1021/jo00094a017

文献信息

• Intermolecular Reactions of .beta.-Lactam-4-ylidenes with Alkenes, Alcohols, and Acetic Acid. Spiro-Fused .beta.-Lactam Cyclopropanes, 4-Alkoxy .beta.-Lactams, and a 4-Acetoxy .beta.-Lactam
  作者：Michel Zoghbi、Stephen E. Horne、John Warkentin

  DOI：10.1021/jo00094a017

  日期：1994.7

  Thermolysis of spiro-fused beta-lactam oxadiazolines in the presence of alkenes gave spiro-fused beta-lactam cyclopropanes. The latter arise through a sequence of reactions beginning with 1,3-dipolar cycloreversion of an oxadiazoline to form N-2 and a short-lived carbonyl ylide. The latter fragments to acetone and a beta-lactam-4-ylidene, which adds to the alkene. Stereospecific additions to dimethyl fumarate and to dimethyl maleate are consistent with a concerted mechanism of cyclopropanation. The ylidenes also form cyclopropanes with alkenes that are not Michael accepters, including styrene and 4-bromo-1-butene. Thermolysis of beta-lactam oxadiazolines in the presence of hydroxylic compounds led to capture of beta-lactam-4-ylidenes by OH insertion, essentially in quantitative yields, as expected for reaction of singlet beta-lactam-4-ylidenes.