2-(Cyclohexyl-imino-methyl)-phenylamine | 22162-61-4

• 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: 2-(Cyclohexyl-imino-methyl)-phenylamine
• 英文别名: 2-(cyclohexanecarboximidoyl)aniline
• CAS: 22162-61-4
• 化学式: C₁₃H₁₈N₂
• 分子量: 202.299
• InChiKey: JBQUUFWSGJWGPY-UHFFFAOYSA-N

物化性质

• 沸点：
  364.1±34.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.87
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(Cyclohexyl-imino-methyl)-phenylamine 在 盐酸 、 六氟异丙醇 、 potassium tert-butylate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 生成 (5-(4-bromophenyl)-1-(2-(1-cyclohexylvinyl)phenyl)-2-phenyl-4,5-dihydro-1H-pyrrol-3-yl)(phenyl)methanone
  参考文献：
  名称：

  Hexafluoroisopropanol Promoted Ring‐Opening‐Cyclization of Donor–Acceptor Cyclopropanes with Primary Amines

  摘要：

  We reveal here a catalyst‐free, ring‐opening‐cyclization of donor‐acceptor cyclopropanes with primary amines to synthesize functionalized dihydropyrroles. This protocol avoids inert conditions and solvents promoted by hexafluoroisopropanol (HFIP). The reaction is quite general with aryl, alkyl, and alicyclic amines. A good number of cyclopropanes bearing keto groups reacted excellently to produce the desired products. Further, we complemented this method with Meldrum's acid‐derived cyclopropanes for synthesizing γ‐lactams. We have demonstrated the post‐synthetic applications of the products and gram‐scale synthesis to highlight the adaptability of this synthetic protocol.

  DOI：

  10.1002/ejoc.202400238
• 作为产物：
  描述：

  2-氨基苯甲腈 、 alkaline earth salt of/the/ methylsulfuric acid 以 四氢呋喃 为溶剂， 生成 2-(Cyclohexyl-imino-methyl)-phenylamine
  参考文献：
  名称：

  Hexafluoroisopropanol Promoted Ring‐Opening‐Cyclization of Donor–Acceptor Cyclopropanes with Primary Amines

  摘要：

  We reveal here a catalyst‐free, ring‐opening‐cyclization of donor‐acceptor cyclopropanes with primary amines to synthesize functionalized dihydropyrroles. This protocol avoids inert conditions and solvents promoted by hexafluoroisopropanol (HFIP). The reaction is quite general with aryl, alkyl, and alicyclic amines. A good number of cyclopropanes bearing keto groups reacted excellently to produce the desired products. Further, we complemented this method with Meldrum's acid‐derived cyclopropanes for synthesizing γ‐lactams. We have demonstrated the post‐synthetic applications of the products and gram‐scale synthesis to highlight the adaptability of this synthetic protocol.

  DOI：

  10.1002/ejoc.202400238

文献信息

• Direct Electrophilic C−H Alkynylation of Unprotected 2-Vinylanilines
  作者：Lucien D. Caspers、Peter Finkbeiner、Boris J. Nachtsheim

  DOI：10.1002/chem.201606026

  日期：2017.2.24

  Unprotected aromatic amines can be used as directing groups in metal‐catalyzed C−H alkynylations of alkenes. By using low amounts of an IrIII catalyst in combination with alkynylbenziodoxolones as electrophilic alkyne‐transfer reagents, highly desirable 1,3‐enynes were isolated in excellent yields of up to 98 % with Z stereoselectivity. A broad substrate scope as well as the high synthetic utility

  未保护的芳族胺可用作金属在烯烃的CH-H炔基化反应中的导向基团。通过使用少量的Ir III催化剂与炔基苯并恶唑烷酮作为亲电炔转移试剂，可以分离出非常理想的1,3-炔烃，Z立体选择性高达98％。广泛的底物范围以及1,3-烯炔的高合成效用使该新方法成为合成五元和六元杂环的有效方法。通过Au I-和N-溴代琥珀酰亚胺介导的exo-dig环化反应，进一步证明了1,3-烯炔进一步衍生为高度取代的喹啉。