N-tert-butoxycarbonyl-4-chloro-2-(3,3-dimethylallyl)aniline | 153779-14-7

• 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: N-tert-butoxycarbonyl-4-chloro-2-(3,3-dimethylallyl)aniline
• 英文别名: tert-butyl N-[4-chloro-2-(3-methylbut-2-enyl)phenyl]carbamate
• CAS: 153779-14-7
• 化学式: C₁₆H₂₂ClNO₂
• 分子量: 295.809
• InChiKey: JFPUCCAXOBXTBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-4-chloro-2-(3,3-dimethylallyl)aniline 在 氢氧化钾 、 sodium tetrahydroborate 、 mercury(II) nitrate 、 mercury(II) oxide 作用下， 生成 N-tert-butoxycarbonyl-5-chloro-2,2-dimethyl-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Amidomercuration-Cyclization of N-tert-Butoxycarbonyl-2-allylaniline Derivatives

  摘要：

  Dilithation of N-tert-butoxycarbonylanilines with tert-butylithium followed by addition of 4-bromo-2-methyl-2-butene affords N-tert-butoxycarbonyl-2-(3,3-dimethylallyl)anilines (3a-e). The mercuric ion-initiated cyclization of compounds (3a-e) was investigated. N-tert-Butoxycarbonyl-4-chloro-2-(3-methyl-2-buten-1-yl)aniline (3b) and the 6-fluoro analogue (3c) readily undergo amidomercuration-cyclization to give N-tert-butoxycarbonyl-5-chloro-2,2-dimethyl-1,2,3,4-tetrahydroquinoline (4b) and N-tert-butoxycarbonyl-8-fluoro-2,2-dimethyl-1,2,3,4-tetrahydroquinoline (4c). Anilides (3a, 3d-e) gave a mixture of tetrahydroquinolines (4a, 4d-e) and the dihydroindoles (5a, 5d-e). N-Ethoxycarbonyl-2-(3-methyl-2-buten-1-yl)aniline (3f) gave mainly the N-ethoxycarbonyl-2,2-dimethyl-1,2,3,4-tetrahydroquinoline (4f).

  DOI：

  10.3987/com-93-6409
• 作为产物：
  描述：

  4-氯-(N-Boc)苯胺 、 1-溴-3-甲基-2-丁烯 在 叔丁基锂 作用下， 生成 N-tert-butoxycarbonyl-4-chloro-2-(3,3-dimethylallyl)aniline
  参考文献：
  名称：

  Amidomercuration-Cyclization of N-tert-Butoxycarbonyl-2-allylaniline Derivatives

  摘要：

  Dilithation of N-tert-butoxycarbonylanilines with tert-butylithium followed by addition of 4-bromo-2-methyl-2-butene affords N-tert-butoxycarbonyl-2-(3,3-dimethylallyl)anilines (3a-e). The mercuric ion-initiated cyclization of compounds (3a-e) was investigated. N-tert-Butoxycarbonyl-4-chloro-2-(3-methyl-2-buten-1-yl)aniline (3b) and the 6-fluoro analogue (3c) readily undergo amidomercuration-cyclization to give N-tert-butoxycarbonyl-5-chloro-2,2-dimethyl-1,2,3,4-tetrahydroquinoline (4b) and N-tert-butoxycarbonyl-8-fluoro-2,2-dimethyl-1,2,3,4-tetrahydroquinoline (4c). Anilides (3a, 3d-e) gave a mixture of tetrahydroquinolines (4a, 4d-e) and the dihydroindoles (5a, 5d-e). N-Ethoxycarbonyl-2-(3-methyl-2-buten-1-yl)aniline (3f) gave mainly the N-ethoxycarbonyl-2,2-dimethyl-1,2,3,4-tetrahydroquinoline (4f).

  DOI：

  10.3987/com-93-6409

文献信息

• Amidomercuration-Cyclization of N-tert-Butoxycarbonyl-2-allylaniline Derivatives
  作者：Jacob Berger、Deborah L. Kerly

  DOI：10.3987/com-93-6409

  日期：——

  Dilithation of N-tert-butoxycarbonylanilines with tert-butylithium followed by addition of 4-bromo-2-methyl-2-butene affords N-tert-butoxycarbonyl-2-(3,3-dimethylallyl)anilines (3a-e). The mercuric ion-initiated cyclization of compounds (3a-e) was investigated. N-tert-Butoxycarbonyl-4-chloro-2-(3-methyl-2-buten-1-yl)aniline (3b) and the 6-fluoro analogue (3c) readily undergo amidomercuration-cyclization to give N-tert-butoxycarbonyl-5-chloro-2,2-dimethyl-1,2,3,4-tetrahydroquinoline (4b) and N-tert-butoxycarbonyl-8-fluoro-2,2-dimethyl-1,2,3,4-tetrahydroquinoline (4c). Anilides (3a, 3d-e) gave a mixture of tetrahydroquinolines (4a, 4d-e) and the dihydroindoles (5a, 5d-e). N-Ethoxycarbonyl-2-(3-methyl-2-buten-1-yl)aniline (3f) gave mainly the N-ethoxycarbonyl-2,2-dimethyl-1,2,3,4-tetrahydroquinoline (4f).