N-(4-acetoxybenzylidene)benzhydrylamine | 161671-24-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-acetoxybenzylidene)benzhydrylamine
• CAS: 161671-24-5
• 化学式: C₂₂H₁₉NO₂
• 分子量: 329.398
• InChiKey: ZVSYRBPUKRQQCN-XQNSMLJCSA-N

物化性质

• 沸点：
  458.6±45.0 °C(predicted)
• 密度：
  1.06±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(4-acetoxybenzylidene)benzhydrylamine 在 palladium on activated charcoal 、 In(OSO₂CF₃)3 molecular sieve 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 diisopropyl 2-(4-acetoxyphenyl)-1-aminoethylphosphonate
  参考文献：
  名称：

  Indium triflate catalyzed reaction of diisopropyl diazomethylphosphonate with imines as a new approach to cis- and trans-aziridine-2-phosphonates

  摘要：

  A new and efficient synthesis of cis- and trans-aziridine-2-phosphonates by metal-catalyzed aziridination reaction of diisopropyl diazomethylphosphonate and substituted aryl imines is reported. By exploring the influence of different Lewis acids employed as catalysts, imine nitrogen substituents, and the solvent effects we conclude that the best results are obtained when N-d iphenylmethyl- substituted benzylimines are reacted with diisopropyl diazomethylphosphonate in methylene chloride at 0 degrees C in the presence of In(OTt)(3) as catalyst. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.042
• 作为产物：
  描述：

  4-乙酰氧基苯甲醛 、 二苯甲胺 在 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 生成 N-(4-acetoxybenzylidene)benzhydrylamine
  参考文献：
  名称：

  Catalytic Asymmetric Aziridination with a Chiral VAPOL−Boron Lewis Acid

  摘要：

  DOI：

  10.1021/ja9905187

文献信息

• A New Chiral BLA Promoter for Asymmetric Aza Diels-Alder and Aldol-Type Reactions of Imines
  作者：Kazuaki Ishihara、Mayumi Miyata、Kouji Hattori、Toshiji Tada、Hisashi Yamamoto

  DOI：10.1021/ja00102a019

  日期：1994.11

  A new type of chiral promoter for double asymmetric inductions of aza Diels-Alder and aldol-type reactions of imines is prepared from trialkyl berates (B(OMe)(3) or B(OPh)(3)) and optically pure binaphthol; X-ray analysis of the boron complex demonstrates that it exists as a Bronsted acid-assisted chiral Lewis acid(BLA). The aldol-type reactions of a number of N-benzhydrylimines derived from aromatic aldehydes with the ketene silyl acetal derived from tert-butyl acetate mediated by the chiral BLA afford beta-amino acid esters with high enantioselectivity. The solution conformations of the BLA.imine complexes have been studied using H-1 NMR analysis and difference NOE measurements. The absolute configurations of the adducts can be understood in terms of a rational model involving an intramolecular hydrogen binding interaction via a Bronsted acid.
• US6258960B1
  申请人：——

  公开号：US6258960B1

  公开（公告）日：2001-07-10