N-[(1S,2R)-2-methylcyclopentyl]aniline

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-[(1S,2R)-2-methylcyclopentyl]aniline
• 化学式: C₁₂H₁₇N
• 分子量: 175.274
• InChiKey: ONZLUKIUQJGXJY-PWSUYJOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  己-5-烯基-苯基-胺 在 正丁基锂 、 zirconocene methyl chloride 作用下， 生成 N-[(1S,2R)-2-methylcyclopentyl]aniline
  参考文献：
  名称：

  Zirconium-Mediated Intramolecular Coupling Reactions of Unsaturated Anilines. Diastereoselective Synthesis of Azetidines

  摘要：

  Imine complexes of zirconocene, generated by a beta-hydrogen abstraction process, which possess a carbon-carbon multiple bond, undergo inter-or intramolecular carbometalation to afford 1,4-cyclohexanediamine or cycloalkylaniline derivatives depending on the relative position of the unsaturated moiety with respect to the imine complex. A new diastereoselective synthesis of azetidines has been developed by treatment of azazirconacyclopentanes with iodine.

  DOI：

  10.1021/jo9705780

文献信息

• Diastereo- and enantioselective reductive amination of cycloaliphatic ketones by preformed chiral palladium complexes
  作者：Armando Cabrera、Pankaj Sharma、F. Javier Pérez-Flores、Luis Velasco、J. Luis Arias、Laura Rubio-Pérez

  DOI：10.1039/c4cy00058g

  日期：——

  An efficient preformed chiral palladium catalyzed direct diastereo- and enantioselective reductive amination of un- and substituted cycloaliphatic ketones with primary aryl amines has been developed.

  已经开发了一种有效的预形成的手性钯与伯芳基胺的未取代和取代的环脂族酮的直接非对映和对映选择性还原胺化反应。
• An Aminopyridinato Titanium Catalyst for the Intramolecular Hydroaminoalkylation of Secondary Aminoalkenes
  作者：Jaika Dörfler、Besnik Bytyqi、Sascha Hüller、Nicola M. Mann、Christian Brahms、Marc Schmidtmann、Sven Doye

  DOI：10.1002/adsc.201500287

  日期：2015.7.6

  2‐(methylamino)pyridinato titanium complex initially synthesized by Kempe is used as catalyst for efficient intramolecular hydroaminoalkylation reactions of secondary aminoalkenes. The corresponding reactions of N‐aryl‐substituted 1‐aminohept‐6‐enes and 1‐aminohex‐5‐enes directly give access to 2‐methylcyclohexyl‐ or 2‐methylcyclopentylamines in good yields. In addition, intramolecular hydroaminoalkylations of an N‐alkyl‐substituted

  由Kempe最初合成的易于获得的2-（甲氨基）吡啶并钛络合物用作仲氨基烯烃的分子内加氢氨基烷基化反应的有效催化剂。N-芳基取代的1-氨基庚6-烯和1-氨基己基5-烯的相应反应可直接获得2-甲基环己基或2-甲基环戊基胺。此外，首次描述了N-烷基取代的仲氨基烯烃和双β-二取代基的分子内加氢氨基烷基化反应。虽然所有产物都是两种非对映异构体的混合物，但在形成2-甲基环戊基胺的过程中观察到更好的反式/顺式比例。
• Zirconium-Mediated Intramolecular Coupling Reactions of Unsaturated Anilines. Diastereoselective Synthesis of Azetidines
  作者：José Barluenga、Roberto Sanz、Francisco J. Fañanás

  DOI：10.1021/jo9705780

  日期：1997.8.1

  Imine complexes of zirconocene, generated by a beta-hydrogen abstraction process, which possess a carbon-carbon multiple bond, undergo inter-or intramolecular carbometalation to afford 1,4-cyclohexanediamine or cycloalkylaniline derivatives depending on the relative position of the unsaturated moiety with respect to the imine complex. A new diastereoselective synthesis of azetidines has been developed by treatment of azazirconacyclopentanes with iodine.