2-(3-methylbut-2-enyl)-cyclohexanone oxime | 240426-81-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(3-methylbut-2-enyl)-cyclohexanone oxime
• 英文别名: N-[2-(3-methylbut-2-enyl)cyclohexylidene]hydroxylamine
• CAS: 240426-81-7
• 化学式: C₁₁H₁₉NO
• 分子量: 181.278
• InChiKey: XJQQETNPYCERQP-UHFFFAOYSA-N

物化性质

• 沸点：
  287.8±9.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-methylbut-2-enyl)-cyclohexanone oxime 在 18-冠醚-6 、 sodium 、 caesium carbonate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 氯苯 为溶剂， 反应 12.5h， 生成
  参考文献：
  名称：

  Domino Aryne Annulation via a Nucleophilic–Ene Process

  摘要：

  1,2-Benzdiyne equivalents possess the unique property that they can react with two arynophiles through iteratively generated 1,2- and 2,3-aryne intermediates. Upon rational modification on the second leaving group of these aryne precursors, a domino aryne annulation approach was developed through a nucleophilic-ene reaction sequence. Various benzo-fused N-heterocyclic frameworks were achievable under transition metal-free conditions with a broad substrate scope.

  DOI：

  10.1021/jacs.8b01005
• 作为产物：
  描述：

  环己酮 在 盐酸羟胺 、 sodium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 7.5h， 生成 2-(3-methylbut-2-enyl)-cyclohexanone oxime
  参考文献：
  名称：

  Domino Aryne Annulation via a Nucleophilic–Ene Process

  摘要：

  1,2-Benzdiyne equivalents possess the unique property that they can react with two arynophiles through iteratively generated 1,2- and 2,3-aryne intermediates. Upon rational modification on the second leaving group of these aryne precursors, a domino aryne annulation approach was developed through a nucleophilic-ene reaction sequence. Various benzo-fused N-heterocyclic frameworks were achievable under transition metal-free conditions with a broad substrate scope.

  DOI：

  10.1021/jacs.8b01005

文献信息

• A New Method for the Generation and Cyclization of Iminyl Radicals via the Hudson Reaction
  作者：Xichen Lin、Didier Stien、Steven M. Weinreb

  DOI：10.1021/ol990720e

  日期：1999.8.1

  [formula: see text] A mild new synthetic procedure has been developed for in situ generation and cyclization of iminyl radicals onto pendant alkenes, followed by functionalization of the resulting carbon radical by one of a variety of trapping reagents. The key process in the method involves production of the iminyl radical via treatment of an aldoxime or ketoxime with readily available 2,6-dimethylbenzenesulfinyl

  [化学式：见正文]已开发出一种温和的新合成程序，用于将亚氨基自由基原位生成和环化到侧链烯烃上，然后通过多种捕集试剂之一将所得碳自由基官能化。该方法的关键过程涉及在-50℃至室温下通过用容易获得的2，6-二甲基苯亚磺酰氯处理醛肟或酮肟来生产亚胺基（Hudson反应）。
• Development of efficient new methodology for generation, cyclization and functional trapping of iminyl and amidyl radicals
  作者：Xichen Lin、Gerald D. Artman、Didier Stien、Steven M. Weinreb

  DOI：10.1016/s0040-4020(01)00878-x

  日期：2001.10

  New methodology has been devised for the generation and subsequent cyclization of iminyl and amidyl radicals under mild conditions. The process involves either the treatment of oximes with 2,6-dimethylbenzenesulfinyl chloride, or the treatment of hydroxamic acids with tert-butylsulfinyl chloride (-50 degreesC to rt), to give the corresponding nitrogen radicals, followed by cyclization onto pendant olefins. Radical traps such as diphenyl diselenide, diphenyl disulfide, and TEMPO can be used to terminate the cyclizations, thus introducing functionality that provides multiple options for further manipulation. In a more convenient procedure, both iminyl and amidyl radical cyclizations can be initiated using commercially available diethyl chlorophosphite which generally provides similar (with diphenyl disulfide and TEMPO) or significantly higher (with diphenyl diselenide) yields of products. (C) 2001 Elsevier Science Ltd. All rights reserved.