2-(4'-叠氮丁基)环戊酮 | 171737-85-2

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 2-(4'-叠氮丁基)环戊酮
• 英文名称: 2-(4'-azidobutyl)cyclopentanone
• 英文别名: 2-(4-azidobutyl)cyclopentanone；2-(4-Azidobutyl)cyclopentan-1-one
• CAS: 171737-85-2
• 化学式: C₉H₁₅N₃O
• 分子量: 181.238
• InChiKey: AXDFXDQDXBNMFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4'-叠氮丁基)环戊酮 在 三氟乙酸 作用下， 反应 1.25h， 以56%的产率得到quinolizidin-4-one
  参考文献：
  名称：

  SYNTHESIS OF AN N-SUBSTITUTED LACTAM USING AN INTRAMOLECULAR SCHMIDT REACTION: FORMATION OF 2,3,11,11a-TETRAHYDRO-1H-BENZO[d]PYRROLO[1,2-a]AZEPIN-5(6H)-ONE

  摘要：

  DOI：

  10.15227/orgsyn.084.0347
• 作为产物：
  描述：

  1-(4-Chloro-butyl)-2-oxo-cyclopentanecarboxylic acid methyl ester 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 2-(4'-叠氮丁基)环戊酮
  参考文献：
  名称：

  Intramolecular Schmidt Reactions of Alkyl Azides with Ketones: Scope and Stereochemical Studies

  摘要：

  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.

  DOI：

  10.1021/ja00147a006

文献信息

• A Schmidt route to 1-azabicyclo[x.y.0]alkanes: a comparison of carbocation stabilizing groups
  作者：William H Pearson、Rajesh Walavalkar

  DOI：10.1016/s0040-4020(01)00353-2

  日期：2001.6

  The intramolecular Schmidt reactions of tertiary alkyl, tertiary benzylic, tertiary propargylic, and tertiary allylic carbocations with tethered azides are reported. Using product analysis and deuterium labeling studies, the role of cation rearrangement prior to Schmidt reaction is reported.

  据报道，叔烷基，叔苄基，叔炔丙基和叔烯丙基碳阳离子与拴系叠氮化物的分子内施密特反应。使用产物分析和氘标记研究，报道了施密特反应之前阳离子重排的作用。