(1S,3R,4S)-endo-2-(4-methoxyphenyl)-3-phenyl-2-azabicyclo[2.2.2]octan-5-one | 1427441-76-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (1S,3R,4S)-endo-2-(4-methoxyphenyl)-3-phenyl-2-azabicyclo[2.2.2]octan-5-one
• 英文别名: 2-endo-(4-methoxyphenyl)-3-phenyl-2-azabicyclo[2,2,2]octan-5-one；(1S,3R,4S)-2-(4-methoxyphenyl)-3-phenyl-2-azabicyclo[2.2.2]octan-5-one
• CAS: 1427441-76-6
• 化学式: C₂₀H₂₁NO₂
• 分子量: 307.392
• InChiKey: SHXJCCUJHJDEHT-HQRMLTQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-环己烯-1-酮 、 N-亚苄基-4-甲氧基苯胺 在 Merrifield resin loaded proline modified dendrigraft second generation polyepichlorohydrin polymer supported copper complex 作用下， 以 四氯化碳 为溶剂， 反应 3.03h， 以90%的产率得到
  参考文献：
  名称：

  Chiral dendrigraft polymer for asymmetric synthesis of isoquinuclidines

  摘要：

  一种具有五羟甲基四羧酸引发的聚环氧氯丙烷核心的手性修饰树枝状聚酰胺胺铜配合物，PEN-G2，在固体树脂支撑体系中被用于合成异喹啉，通过环己酮和亚胺之间的氮杂Diels-Alder反应。

  DOI：

  10.1039/c6ra15548k

文献信息

• Design of primary amine-functionalized polymer containing chiral isosorbide in the main chain for the asymmetric synthesis of isoquinuclidine derivatives
  作者：K. Hiba、K. Sreekumar

  DOI：10.1039/d1nj05868a

  日期：——

  The present article is concerned with the synthesis, characterization, and application of a novel amine-functionalized optically active polymer consisting of isosorbide units attached in the main chain. This polymer could be used as a chiral homogeneous organocatalyst for the one-pot three component asymmetric synthesis of isoquinuclidine derivatives via aza-Diels–Alder reaction. Recyclability, the

  本文关注一种新型胺官能化光学活性聚合物的合成、表征和应用，该聚合物由连接在主链上的异山梨醇单元组成。该聚合物可用作手性均相有机催化剂，用于通过aza-Diels-Alder 反应一锅三组分不对称合成异奎宁环衍生物。可回收性、催化剂用量少、后处理简单、非对映选择性优异、对映选择性适中、产品收率高，使含伯胺官能化手性聚合物（Chiral-ISO-PECH-Amine）的异山梨醇成为一种潜在的催化剂用于合成异奎宁环衍生物。
• Aza-Diels–Alder reaction catalyzed by novel chiral metalocomplex Brønsted acids
  作者：Victor I. Maleev、Tat’yana V. Skrupskaya、Lidia V. Yashkina、Anna F. Mkrtchyan、Ashot S. Saghyan、Michayl M. Il’in、Denis A. Chusov

  DOI：10.1016/j.tetasy.2013.01.011

  日期：2013.2

  A series of Co(III) anionic complexes of Schiff bases obtained from salicylaldehydes and enantiomerically pure amino acids has been synthesized. The outersphere counterion was exchanged by H+ and the novel chiral Bronsted acids were used to induce asymmetry into an aza-Diels-Alder reaction. The influence of the temperature, solvent polarity, and structural modification of the chiral anions on the enantioselectivity of the process has also been investigated. (C) 2013 Elsevier Ltd. All rights reserved.
• Enantioselective oxidative-coupling of polycyclic phenols
  作者：Shinobu Takizawa、Junpei Kodera、Yasushi Yoshida、Makoto Sako、Stefanie Breukers、Dieter Enders、Hiroaki Sasai

  DOI：10.1016/j.tet.2014.01.017

  日期：2014.3

  Enantioselective oxidative-coupling of polycyclic phenols, such as 2-anthracenol, 9- or 3-phenanthrol, and 5-chrysenol was established by using vanadium(V/IV) catalysis under air or 02 as a co-oxidant. In the vanadium catalyzed reaction, the corresponding coupling products were obtained in good to excellent yields with up to 93% enantiomeric excess. (C) 2014 Elsevier Ltd. All rights reserved.
• Chiral dendrigraft polymer for asymmetric synthesis of isoquinuclidines
  作者：G. Smitha、K. Sreekumar

  DOI：10.1039/c6ra15548k

  日期：——

  A copper complex of chiral modified dendrigraft amidoamine polymer with a pentaerythritol initiated polyepichlorohydrin core, PEN-G₂, on a solid resin support is employed in the synthesis of isoquinuclidines via aza Diels–Alder reaction between cyclohexenone and imines.

  一种具有五羟甲基四羧酸引发的聚环氧氯丙烷核心的手性修饰树枝状聚酰胺胺铜配合物，PEN-G2，在固体树脂支撑体系中被用于合成异喹啉，通过环己酮和亚胺之间的氮杂Diels-Alder反应。