(aS)-N-(2-溴苯基)-alpha-甲基-苯甲胺 | 291545-04-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (aS)-N-(2-溴苯基)-alpha-甲基-苯甲胺
• 英文名称: (2-bromophenyl)-(S)-α-methylbenzylamine
• 英文别名: 2-bromo-N-[(S)-1-phenylethyl]aniline；(S)-2-Bromo-N-(1-phenylethyl)-aniline；2-bromo-N-[(1S)-1-phenylethyl]aniline
• CAS: 291545-04-5
• 化学式: C₁₄H₁₄BrN
• 分子量: 276.176
• InChiKey: LTRJAMPTYSTWNQ-NSHDSACASA-N

物化性质

• 沸点：
  354.5±25.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  (aS)-N-(2-溴苯基)-alpha-甲基-苯甲胺 在 tris-(dibenzylideneacetone)dipalladium(0) 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 N,N-二异丙基乙胺 、 sodium t-butanolate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 11.67h， 生成 N-[(1S)-1-phenylethyl]-N-[2-[[(1S)-1-phenylethyl]amino]phenyl]acetamide
  参考文献：
  名称：

  A Versatile Synthesis of Substituted Benzimidazolium Salts by an Amination/Ring Closure Sequence

  摘要：

  [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.

  DOI：

  10.1021/ol016254m
• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 、 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， 以81%的产率得到(aS)-N-(2-溴苯基)-alpha-甲基-苯甲胺
  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

• The first enantiomerically pure thiadiazol-3-one 1-oxide and thiatriaza-indene 3-oxide systems chiral at the sulfur atom
  作者：Benjamin R. Buckley、Stephen P. Neary、Mark R.J. Elsegood

  DOI：10.1016/j.tetasy.2010.07.025

  日期：2010.8

  The first synthesis of an enantiomerically pure C-2 symmetric benzothiadiazole 2-oxide is described along with the first synthesis of an enantiomerically thiadiazol-3-one 1-oxide and a thiatriaza-indene 3-oxide system both chiral at the sulfur atom. Excellent levels of diastereoselectivity were observed in the SO installation step, that is, the reaction of the prerequisite bis-amines with thionyl chloride at ambient temperature. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of chiral N,N′-disubstituted 1,2-benzenediamines from o-dibromobenzene
  作者：Felix M Rivas、Uzma Riaz、Steven T Diver

  DOI：10.1016/s0957-4166(00)00124-5

  日期：2000.5

  Palladium-catalyzed amination of o-dibromobenzene provided chiral N,N'-disubstituted 1,2-benzenediamines in good to excellent yields. The amination was executed stepwise and in one pot to give unsymmetrically and symmetrically substituted 1,2-benzenediamines. Incorporation of chiral primary amines was possible without racemization using catalytic Pd(2)dba(3)-BINAP. (C) 2000 Elsevier Science Ltd. All rights reserved.
• A new paradigm in N-heterocyclic carbenoid ligands
  作者：Philip C. Bulman Page、Benjamin R. Buckley、Steven D.R. Christie、Mark Edgar、Andrew M. Poulton、Mark R.J. Elsegood、Vickie McKee

  DOI：10.1016/j.jorganchem.2005.09.015

  日期：2005.12

  We report a new class of very readily prepared chiral N-heterocyclic carbenoid ligand that also contains two different types of chirality: an asymmetric centre and an atropoisomeric unit, but contained in two separate N-substituents, such that both can easily be varied. In addition to its simplicity and flexibility, this approach has potential advantages over systems containing only atropoisomeric units, because the inclusion of an additional fixed asymmetric centre means that the atropoisomers are diastereoisomers and therefore chemically distinct entities. Complexation to a metal centre increases the barrier to rotation in the atropoisomeric unit so that the two diastercoisomers may be separable by simple methods such as standard chromatography. In addition, a novel cis-substituted palladium complex has been characterised by X-ray crystallography. (c) 2005 Elsevier B.V. All rights reserved.
• 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.
• Enantiomerically Pure N Chirally Substituted 1,3-Benzazaphospholes: Synthesis, Reactivity toward <i>t</i>BuLi, and Conversion to Functionalized Benzazaphospholes and Catalytically Useful Dihydrobenzazaphospholes
  作者：Mohammed Ghalib、Peter G. Jones、Sergej Lysenko、Joachim W. Heinicke

  DOI：10.1021/om401184n

  日期：2014.2.10

  Catalytic C-P coupling of chiral o-bromoanilines 1a-c to the corresponding o-phosphonoanilines 2a-c, reduction to the phosphines 3a-c, and final acid-catalyzed cyclocondensation represents a convenient access to the title compounds 4-c. Reaction of 4a,b with tBuLi allows solvent-dependent directed lithiation leading either to 2-lithiobenzazaphospholes with a P=CLi NR substructure (in Et2O/KOtBu), in the case of anisyl substitution accompanied by partial additional lithiation in o-position of the MeO-group, or to regiospecific "normal" addition with formation of -P-(tBu)-CHLi-NR- species. These were trapped by ClSiMe3, CO2, or MeOH to give the corresponding substitution products 7b, 8b, 10b, 11a,b and 12a,b, respectively. 12a,b, containing the P-C-COOH structural unit, forms with Ni(COD)(2) in THF very efficient ethylene oligomerization catalysts With high selectivity for linear alpha-olefins. The structure elucidation of the products is based on conclusive solution NMR data and crystal structure analyses of the 1-(1S)-anisylethyl compounds 3b and 4b.