(1R,2R,3S)-2,3-Diphenyl-cyclopropanecarboxylic acid ((S)-1-phenyl-ethyl)-amide | 314050-05-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1R,2R,3S)-2,3-Diphenyl-cyclopropanecarboxylic acid ((S)-1-phenyl-ethyl)-amide
• CAS: 314050-05-0
• 化学式: C₂₄H₂₃NO
• 分子量: 341.453
• InChiKey: VXCFJLWPZWAIDB-AIZKBTNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S)-2,3-Diphenyl-cyclopropanecarboxylic acid ((S)-1-phenyl-ethyl)-amide 在 Li(+)-exchanged Y-zeolite 作用下， 以 正己烷 为溶剂， 生成 2,3-Diphenyl-cyclopropanecarboxylic acid ((S)-1-phenyl-ethyl)-amide
  参考文献：
  名称：

  Confined space and cations enhance the power of a chiral auxiliary: photochemistry of 1,2-diphenylcyclopropane derivativesElectronic supplementary information (ESI) available: experimental details of irradiation, extraction and analysis of products, and representative synthesis and spectral data of reactant cis and product trans isomers; total number of pages 21. See http://www.rsc.org/suppdata/cc/b2/b200640e/

  摘要：

  碱离子交换的Y型沸石显著增强了包含远离手性辅助基团的多种顺式-1,2-二苯基环丙烷衍生物的光异构化中的不对称诱导。

  DOI：

  10.1039/b200640e
• 作为产物：
  描述：

  ethyl ester of 2β,3β-diphenylcyclopropane-1α-carboxylic acid 在 4-二甲氨基吡啶 、 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (1R,2R,3S)-2,3-Diphenyl-cyclopropanecarboxylic acid ((S)-1-phenyl-ethyl)-amide
  参考文献：
  名称：

  Confined space and cations enhance the power of a chiral auxiliary: photochemistry of 1,2-diphenylcyclopropane derivativesElectronic supplementary information (ESI) available: experimental details of irradiation, extraction and analysis of products, and representative synthesis and spectral data of reactant cis and product trans isomers; total number of pages 21. See http://www.rsc.org/suppdata/cc/b2/b200640e/

  摘要：

  碱离子交换的Y型沸石显著增强了包含远离手性辅助基团的多种顺式-1,2-二苯基环丙烷衍生物的光异构化中的不对称诱导。

  DOI：

  10.1039/b200640e

文献信息

• Reactive-State Spin-Dependent Diastereoselective Photoisomerization of <i>trans,trans</i>-2,3-Diphenylcyclopropane-1- carboxylic Acid Derivatives Included in Zeolites
  作者：J. Sivaguru、Tetsuya Shichi、V. Ramamurthy

  DOI：10.1021/ol026695l

  日期：2002.11.1

  [reaction: see text] The asymmetric induction facilitated by a chiral auxiliary during the photoisomerization of trans,trans-2,3-diphenylcyclopropane derivatives depends on the medium (solution vs zeolite) and the reactive state (singlet vs triplet). Within zeolites, direct excitation most likely proceeds via a zwitterionic intermediate, while triplet sensitization most likely proceeds via a diradical

  [反应：见正文]在反式，反式-2,3-二苯基环丙烷衍生物的光异构化过程中，由手性助剂促进的不对称诱导取决于介质（溶液对沸石）和反应态（单体对三重态）。在沸石中，直接激发最有可能通过两性离子中间体进行，而三重态敏化则最有可能通过双自由基中间体进行。
• The influence of chiral auxiliaries is enhanced within zeolites
  作者：Sivaguru Jayaraman、Sundararajan Uppili、Arunkumar Natarajan、Abraham Joy、Kenneth C.W. Chong、Matthew R. Netherton、Alla Zenova、J.R. Scheffer*、V. Ramamurthy

  DOI：10.1016/s0040-4039(00)01459-3

  日期：2000.10

  Zeolites significantly enhance the influence of chiral auxiliaries during photochemical reactions. The generality of this phenomenon has been tested with three independent examples. Chiral auxiliaries that lead to 1:1 mixtures of diastereomers in solution give products in up to 80% diastereomeric excess in the presence of faujasite type zeolites. (C) 2000 Elsevier Science Ltd. All rights reserved.