5-[chloro(tert-butyl)amino]-4,4-dimethylpent-1-ene | 494198-95-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-[chloro(tert-butyl)amino]-4,4-dimethylpent-1-ene
• 英文别名: N-tert-butyl-N-chloro-2,2-dimethylpent-4-en-1-amine
• CAS: 494198-95-7
• 化学式: C₁₁H₂₂ClN
• 分子量: 203.755
• InChiKey: OZJNAGZYJDFLIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-[chloro(tert-butyl)amino]-4,4-dimethylpent-1-ene 在 sodium iodide 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以95%的产率得到1-tert-butyl-3-chloro-5,5-dimethylpiperidine
  参考文献：
  名称：

  An Efficient Synthesis of Fluorinated Azaheterocycles by Aminocyclization of Alkenes

  摘要：

  A general and efficient approach to important fluorinated azaheterocycles has been developed by incorporating nucleophilic fluorination into alkene difunctionalization. This intramolecular aminofluorination transformation of alkenes has been achieved via the aminocyclization of reactive unsaturated N-iodoamines, which can be generated in situ from either unsaturated N-chloramines or their amine precursors in a one-pot protocol.

  DOI：

  10.1021/ol4003866
• 作为产物：
  描述：

  2,2-二甲基-4-戊烯醛 在 N-氯代丁二酰亚胺 、 sodium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 5-[chloro(tert-butyl)amino]-4,4-dimethylpent-1-ene
  参考文献：
  名称：

  Iodide-Catalysed Cyclization of Unsaturated N-Chloroamines: A New Way to Synthesise 3-Chloropiperidines

  摘要：

  DOI：

  10.1002/1099-0690(200209)2002:18<3171::aid-ejoc3171>3.0.co;2-l

文献信息

• One-Pot Synthesis of 3-Azido- and 3-Aminopiperidines by Intramolecular Cyclization of Unsaturated Amines
  作者：Gerardo X. Ortiz、Bora Kang、Qiu Wang

  DOI：10.1021/jo4022666

  日期：2014.1.17

  A highly efficient one-pot synthesis of 3-azidopiperidines has been achieved by an intramolecular cyclization of unsaturated amines that allows for the nucleophilic installation of an azide moiety. This method unlocks the versatile employment of the azide functionality in the preparation and biological studies of piperidine-containing structures. This strategy has been expanded for the direct incorporation

  通过不饱和胺的分子内环化可以实现叠氮基部分的亲核安装，从而实现了3-叠氮基哌啶的高效一锅合成。该方法在含哌啶结构的制备和生物学研究中开启了叠氮化物功能的广泛应用。该策略已经扩展，可以直接掺入各种氮亲核试剂，因此可以快速，模块化地合成具有重要药物和生物学意义的3-氨基和3-amidopiperidines。特别值得注意的是，这种转化的区域选择性使得能够形成反马尔可夫尼科夫型加合物，从而补充了基于马尔可夫尼科夫的烯烃氨基官能化方法。
• Iodide-Catalysed Cyclization of Unsaturated N-Chloroamines: A New Way to Synthesise 3-Chloropiperidines
  作者：Michael Noack、Richard Göttlich

  DOI：10.1002/1099-0690(200209)2002:18<3171::aid-ejoc3171>3.0.co;2-l

  日期：2002.9
• An Efficient Synthesis of Fluorinated Azaheterocycles by Aminocyclization of Alkenes
  作者：Hai-Tsang Huang、Tyler C. Lacy、Barbara Błachut、Gerardo X. Ortiz、Qiu Wang

  DOI：10.1021/ol4003866

  日期：2013.4.19

  A general and efficient approach to important fluorinated azaheterocycles has been developed by incorporating nucleophilic fluorination into alkene difunctionalization. This intramolecular aminofluorination transformation of alkenes has been achieved via the aminocyclization of reactive unsaturated N-iodoamines, which can be generated in situ from either unsaturated N-chloramines or their amine precursors in a one-pot protocol.