N-(2-naphthylmethyl)cinchoninium bromide

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 金鸡纳生物碱
• 英文名称: N-(2-naphthylmethyl)cinchoninium bromide
• 英文别名: (S)-[(2R,4S,5R)-5-ethenyl-1-(naphthalen-2-ylmethyl)-1-azoniabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethanol;bromide
• 化学式: Br*C₃₀H₃₁N₂O
• 分子量: 515.493
• InChiKey: UZWPQFQUGNRUIT-SFBVTQKHSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴甲基萘 、 辛可宁 以 四氢呋喃 为溶剂， 生成 N-(2-naphthylmethyl)cinchoninium bromide
  参考文献：
  名称：

  相转移催化条件下的催化不对称霍纳-沃兹沃斯-埃蒙斯反应

  摘要：

  描述了由金鸡宁衍生的季铵盐作为相转移催化剂促进的催化不对称Horner-Wadsworth-Emmons反应。在温和的反应条件下用膦酸酯处理前手性酮1，得到相应的所需产物，其中等对映体过量。

  DOI：

  10.1016/s0040-4039(98)00442-0

文献信息

• Catalytic asymmetric Horner-Wadsworth-Emmons reaction under phase-transfer-catalyzed conditions
  作者：Shigeru Arai、Seiji Hamaguchi、Takayuki Shioiri

  DOI：10.1016/s0040-4039(98)00442-0

  日期：1998.5

  The catalytic asymmetric Horner-Wadsworth-Emmons reaction promoted by quaternary ammonium salts derived from cinchonine as a phase-transfer catalyst is described. Treatment of the prochiral ketone 1 with phosphonates under mild reaction conditions afforded the corresponding desired products in moderate enantiomeric excess.

  描述了由金鸡宁衍生的季铵盐作为相转移催化剂促进的催化不对称Horner-Wadsworth-Emmons反应。在温和的反应条件下用膦酸酯处理前手性酮1，得到相应的所需产物，其中等对映体过量。
• [EN] PREPARATION OF SUBSTITUTED 2-HYDROXYGIBBA-1(10A), 2, 4, 4B-TETRAEN-6-ONES<br/>[FR] PRÉPARATION DE 2-HYDROXYGIBBA-1(10A), 2, 4, 4B-TÉTRAEN-6-ONES SUBSTITUÉES
  申请人：MERCK & CO INC

  公开号：WO2007081895A2

  公开（公告）日：2007-07-19

  [EN] The instant invention describes processes for synthesizing substituted 2-hydroxygibba-1(10a),2,4,4b-tetraen-6-ones.
  [FR] L'invention concerne des procédés de synthèse de 2-hydroxygibba-1(10a),2,4,4b-tétraen-6-ones substituées.
• Asymmetric synthesis of N-aryl aziridines
  作者：João Aires-de-Sousa、Sundaresan Prabhakar、Ana M. Lobo、Ana M. Rosa、Mário J.S. Gomes、Marta C. Corvo、David J. Williams、Andrew J.P. White

  DOI：10.1016/s0957-4166(01)00548-1

  日期：2002.1

  The reactions of a variety of N-arylhydroxamates as nitrogen transfer reagents to acryloyl derivatives of (-)-8-phenylmenthol, (-)-quinine and (-)-Oppolzer's sultam acting as Michael acceptors was studied. Poor to modest diastereoselection was observed in the formation of aziridines. The absolute structure of one of the pure diastereomers secured from Oppolzer's auxiliary was established by X-ray crystallography and hence the absolute configuration of the derived methyl-N-phenylaziridine-2-carboxylate could be assigned. Whilst only poor facial selectivity was observed for chiral hydroxamic acid prepared from dehydroabietic acid, moderate to good enantioselection of aziridines could be achieved with the chiral quaternary salts based on cinchona alkaloids, especially with that of cinchonine. A model is presented to explain the origin of enantio selection and a mechanism is proposed for the aziridination reaction. (C) 2002 Elsevier Science Ltd. All rights reserved.