(4-bromo-phenacyl)-triphenyl-arsonium; bromide | 76285-34-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-bromo-phenacyl)-triphenyl-arsonium; bromide
• 英文别名: (4-Brom-phenacyl)-triphenyl-arsonium; Bromid；p-Brombenzoylmethyl-triphenylarsoniumbromid；[2-(4-Bromophenyl)-2-oxoethyl]-triphenylarsanium;bromide
• CAS: 76285-34-2
• 化学式: Br*C₂₆H₂₁AsBrO
• 分子量: 584.182
• InChiKey: VWAXRTBRMKKPGU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-bromo-phenacyl)-triphenyl-arsonium; bromide 、 N,N-二甲基苯胺 在 氢溴酸 作用下， 反应 7.0h， 以39%的产率得到2-(4-bromophenyl)-1-methyl-1H-indole
  参考文献：
  名称：

  Reaction of Phenacyltriphenylarsonium Bromides withN-Methylaniline andN,N-Dimethylaniline

  摘要：

  苯基三苯基胂溴化物与 N-甲基苯胺反应主要生成 2-苯基吲哚和 1-甲基-2-苯基吲哚。胂盐与 N,N-二甲基苯胺的相应反应没有得到任何吲哚，而是得到了一种简单的亲核取代产物，即 α-4′-（二甲基氨基）脱氧苯偶姻。但是，后一种反应在氢溴酸存在下进行时，通过 N,N-二甲基苯胺的去甲基化，可以得到 1-甲基-2-苯基吲哚。

  DOI：

  10.1246/bcsj.53.2423
• 作为产物：
  描述：

  三苯胂 、 2,4'-二溴苯乙酮 生成 (4-bromo-phenacyl)-triphenyl-arsonium; bromide
  参考文献：
  名称：

  Arsonium Compounds. II

  摘要：

  DOI：

  10.1021/ja01870a028

文献信息

• Highly enantioselective tandem cyclopropanation/Wittig reaction of α,β-unsaturated aldehydes with arsonium ylides catalyzed by recyclable dendritic catalyst
  作者：Yun-Hui Zhao、Chang-Wu Zheng、Gang Zhao、Wei-Guo Cao

  DOI：10.1016/j.tetasy.2008.02.022

  日期：2008.4

  A novel tandem cyclopropanation/Wittig reaction of alpha,beta-unsaturated aldehydes with arsonium ylides using a chiral 2-trimethylsilanyloxy-methyl-pyrrolidine-based dendritic catalyst is described. Good yields (up to 86%), and high diastereoselectivities (up to dr = 99: 1) and enantioselectivities (up to 99% ee) were obtained under simple and mild reaction conditions. The catalyst can be recycled without any loss in activity. (c) 2008 Elsevier Ltd. All rights reserved.
• Organocatalytic asymmetric cyclopropanation of α,β-unsaturated aldehydes with arsonium ylides
  作者：Yun-Hui Zhao、Gang Zhao、Wei-Guo Cao

  DOI：10.1016/j.tetasy.2007.10.007

  日期：2007.10

  A novel organocatalytic asymmetric cyclopropanation of alpha,beta-unsaturated aldehydes with arsonium ylides using diphenylprolinol silylether as a catalyst is described. A variety of chiral cyclopropyl aldehydes are obtained in moderate to good yields with up to 99:1 dr (diastereomeric ratio) and 99% ee under simple and mild reaction conditions. (c) 2007 Elsevier Ltd. All rights reserved.
• Arsonium Compounds. II
  作者：F. F. Blicke、Hobart H. Willard、J. T. Taras

  DOI：10.1021/ja01870a028

  日期：1939.1
• Reaction of Phenacyltriphenylarsonium Bromides with<i>N</i>-Methylaniline and<i>N</i>,<i>N</i>-Dimethylaniline
  作者：Raj Kumar Bansal、Gope Bhagchandani

  DOI：10.1246/bcsj.53.2423

  日期：1980.8

  Reaction of phenacyltriphenylarsonium bromide with N-methylaniline furnished 2-phenylindole predominantly together with 1-methyl-2-phenylindole. The corresponding reaction of the arsonium salt with N,N-dimethylaniline did not give any indole, instead a simple nucleophilic substituted product, α-4′-(dimethylamino)deoxybenzoin was obtained. But, the latter reaction on being carried out in presence of hydrobromic acid afforded 1-methyl-2-phenylindole by the demethylation of N,N-dimethylaniline.

  苯基三苯基胂溴化物与 N-甲基苯胺反应主要生成 2-苯基吲哚和 1-甲基-2-苯基吲哚。胂盐与 N,N-二甲基苯胺的相应反应没有得到任何吲哚，而是得到了一种简单的亲核取代产物，即 α-4′-（二甲基氨基）脱氧苯偶姻。但是，后一种反应在氢溴酸存在下进行时，通过 N,N-二甲基苯胺的去甲基化，可以得到 1-甲基-2-苯基吲哚。