(2-bromophenyl)-(S)-1-cyclohexylethylamine | 361979-01-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2-bromophenyl)-(S)-1-cyclohexylethylamine
• 英文别名: 2-bromo-N-[(1S)-1-cyclohexylethyl]aniline
• CAS: 361979-01-3
• 化学式: C₁₄H₂₀BrN
• 分子量: 282.224
• InChiKey: NBACXSMFASDNGY-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2-bromophenyl)-(S)-1-cyclohexylethylamine 在 tris(dibenzylideneacetone)dipalladium (0) 、 盐酸羟胺 、 sodium acetate 、 对甲苯磺酸 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 9.04h， 生成 1-[(S)-1-cyclohexylethyl]-1H-benzimidazole
  参考文献：
  名称：

  Aromatic Amination/Imination Approach to Chiral Benzimidazoles

  摘要：

  The powerful Buchwald-Hartwig amination was utilized for the construction of the benzimidazole nucleus with the substituted nitrogen atom bearing a chiral substituent. A successive amination/imination was followed by an acid-catalyzed ring closure step to give the benzimidazole ring. The products were deprotonated and acylated at the C2 position and could be alkylated on nitrogen to give chiral benzimidazolium salts.

  DOI：

  10.1021/jo016251n
• 作为产物：
  描述：

  [(1S)-1-cyclohexylethyl]amine 、 1,2-二溴苯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 1.5h， 生成 (2-bromophenyl)-(S)-1-cyclohexylethylamine
  参考文献：
  名称：

  新型苯并咪唑鎓盐的合成及其在醛类不对称芳构化中的应用

  摘要：

  由1,2-二溴苯设计并合成了一系列新型的手性苯并咪唑盐，它们是N-杂环卡宾配体的前体。原位制备的相应碳烯在芳族醛的不对称Rh催化芳基化反应中进行测试，从而提供了高收率和中等对映选择性的手性二芳基甲醇。

  DOI：

  10.1016/j.tetlet.2016.06.023

文献信息

• A Versatile Synthesis of Substituted Benzimidazolium Salts by an Amination/Ring Closure Sequence
  作者：Felix M. Rivas、Uzma Riaz、Anthony Giessert、Jason A. Smulik、Steven T. Diver

  DOI：10.1021/ol016254m

  日期：2001.8.1

  [GRAPHICS]A new method to produce benzimidazolium salts based on a successive Buchwald-Hartwig amination and ring closure is reported. A variety of different benzimidazolium salts can be prepared using this procedure. Amines that bear an alpha -chiral group undergo the reaction to furnish chiral benzimidazolium salts. The salts that lack a C2 substituent on the heterocycle are readily deprotonated to give nucleophilic carbenes.
• Synthesis of new benzimidazolium salts and their application in the asymmetric arylation of aldehydes
  作者：Wei-Ping He、Bi-Hui Zhou、Ya-Li Zhou、Xiang-Rong Li、Li-Mei Fan、Hao-Wen Shou、Jie Li

  DOI：10.1016/j.tetlet.2016.06.023

  日期：2016.7

  precursor of N-heterocyclic carbene ligands, were designed and synthesized from 1,2-dibromobenzene. In situ prepared corresponding carbenes were tested in asymmetric Rh-catalyzed arylation of aromatic aldehydes, affording chiral diarylmethanols with high yields and moderate enantioselectivities.

  由1,2-二溴苯设计并合成了一系列新型的手性苯并咪唑盐，它们是N-杂环卡宾配体的前体。原位制备的相应碳烯在芳族醛的不对称Rh催化芳基化反应中进行测试，从而提供了高收率和中等对映选择性的手性二芳基甲醇。
• Aromatic Amination/Imination Approach to Chiral Benzimidazoles
  作者：Felix M. Rivas、Anthony J. Giessert、Steven T. Diver

  DOI：10.1021/jo016251n

  日期：2002.3.1

  The powerful Buchwald-Hartwig amination was utilized for the construction of the benzimidazole nucleus with the substituted nitrogen atom bearing a chiral substituent. A successive amination/imination was followed by an acid-catalyzed ring closure step to give the benzimidazole ring. The products were deprotonated and acylated at the C2 position and could be alkylated on nitrogen to give chiral benzimidazolium salts.