11a-Methyl-1,2,3,6,11,11a-hexahydro-benzo[d]pyrrolo[1,2-a]azepin-5-one | 137125-38-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 11a-Methyl-1,2,3,6,11,11a-hexahydro-benzo[d]pyrrolo[1,2-a]azepin-5-one
• 英文别名: 11a-methyl-2,3,6,11-tetrahydro-1H-pyrrolo[2,1-b][3]benzazepin-5-one
• CAS: 137125-38-3
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: CKJKDSYQIRAFIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  3-(3-Azido-propyl)-3-methyl-3,4-dihydro-1H-naphthalen-2-one 在 三氟乙酸 作用下， 反应 0.33h， 以91%的产率得到11a-Methyl-1,2,3,6,11,11a-hexahydro-benzo[d]pyrrolo[1,2-a]azepin-5-one
  参考文献：
  名称：

  Intramolecular Schmidt reaction of alkyl azides

  摘要：

  DOI：

  10.1021/ja00023a065

文献信息

• Intramolecular Schmidt Reactions of Alkyl Azides with Ketones: Scope and Stereochemical Studies
  作者：Gregory L. Milligan、Craig J. Mossman、Jeffrey Aube

  DOI：10.1021/ja00147a006

  日期：1995.10

  The intramolecular Schmidt reaction of alkyl azides and ketones has been demonstrated. The reaction is proposed to occur via initial attack of an azide on a ketone activated by a variety of protic or Lewis acids, including trifluoroacetic acid, titanium tetrachloride, and others. The resulting azidohydrin undergoes a direct rearrangement to afford the product amide and molecular nitrogen. When cyclic ketones are used, fused bicyclic lactams of types encountered in a wide variety of natural products are obtained. Although the distance allowed between the carbonyl group and the alkyl azide is quite restricted, the reaction is general with respect to the ketone component, including acyclic ketones and cyclic substrates ranging from standard to large ring sizes. The reaction also succeeds with aldehydes, although elimination or hydride migration products compete. In several cases examined, the reaction was found to proceed with retention of configuration at the migrating carbon. Competing reactions with beta-diketones and alpha,beta-unsaturated ketones were found to predominate over ring expansion.