Quinoxaline-2-carboxaldehyde-1,4-dioxide hydrate | 76285-35-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Quinoxaline-2-carboxaldehyde-1,4-dioxide hydrate
• 英文别名: acetyl-p-methoxyphenyltriphenylarsonium bromide；p-Anisoylmethyl-triphenylarsoniumbromid
• CAS: 76285-35-3
• 化学式: Br*C₂₇H₂₄AsO₂
• 分子量: 535.312
• InChiKey: WOACBCGNJINIGR-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.05
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  Quinoxaline-2-carboxaldehyde-1,4-dioxide hydrate 、 N,N-二甲基苯胺 在 氢溴酸 作用下， 反应 7.0h， 以35%的产率得到2-(4-甲氧基苯基)-1-甲基吲哚
  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

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.
• Preparation of acetylstyrene- and benzoylstyrene-tricarbonylchromium, and of 1-acetyl- and 1-benzoyl-2-ferrocenylethylene
  作者：Jiling Huang、Yao-Zeng Huang

  DOI：10.1016/0022-328x(91)83240-5

  日期：1991.8

  The title compounds were synthesized by the reaction of a variety of arsonium salts with benzaldehyde tricarbonyl chromium or monoformyl ferrocene in the presence of K2CO3 at room temperature under phase transfer conditions, giving good yields.
• 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.