2R,3R-diphenylcyclopropane-1-carboxylic acid | 787620-71-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2R,3R-diphenylcyclopropane-1-carboxylic acid
• 英文别名: trans-2,3-Diphenyl-cyclopropancarbonsaeure；(2R,3R)-2,3-diphenylcyclopropane-1-carboxylic acid
• CAS: 787620-71-7
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: CNOVFFZZQUCFDY-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2R,3R-diphenylcyclopropane-1-carboxylic acid 、 (S)-(-)-1-(1-萘基)乙胺 在 4-二甲氨基吡啶 、 1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide methiodide 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3R)-2,3-Diphenyl-cyclopropanecarboxylic acid ((S)-1-naphthalen-1-yl-ethyl)-amide
  参考文献：
  名称：

  Enhanced Diastereoselectivity via Confinement:  Photoisomerization of 2,3-Diphenylcyclopropane-1-carboxylic Acid Derivatives within Zeolites

  摘要：

  From the perspective of asymmetric induction, the photochemistry of 24 chiral esters and amides of cis-2,3-diphenylcyclopropane-1-carboxylic acid from excited singlet and triplet states has been investigated within zeolites. The chiral auxiliaries placed at a remote location from the isomerization site functioned far better within a zeolite than in solution. Generally, chiral auxiliaries with an aromatic or a carbonyl substituent performed better than the ones containing only alkyl substituents. A model based on cation-binding-dependent flexibility of the chiral auxiliary accounts for the observed variation in de between aryl (and carbonyl) and alkyl chiral auxiliaries within zeolites. Cation-dependent diastereomer switch was also observed in select examples.

  DOI：

  10.1021/jo049365i
• 作为产物：
  描述：

  二氮杂甲苯 在 dirhodium tetraacetate 、 sodium hydroxide 、 sodium hypochlorite 、 oxithiane derivative 、 potassium iodide 作用下， 以 甲苯 为溶剂， 反应 19.5h， 生成 2R,3R-diphenylcyclopropane-1-carboxylic acid
  参考文献：
  名称：

  Enhanced Diastereoselectivity via Confinement:  Photoisomerization of 2,3-Diphenylcyclopropane-1-carboxylic Acid Derivatives within Zeolites

  摘要：

  From the perspective of asymmetric induction, the photochemistry of 24 chiral esters and amides of cis-2,3-diphenylcyclopropane-1-carboxylic acid from excited singlet and triplet states has been investigated within zeolites. The chiral auxiliaries placed at a remote location from the isomerization site functioned far better within a zeolite than in solution. Generally, chiral auxiliaries with an aromatic or a carbonyl substituent performed better than the ones containing only alkyl substituents. A model based on cation-binding-dependent flexibility of the chiral auxiliary accounts for the observed variation in de between aryl (and carbonyl) and alkyl chiral auxiliaries within zeolites. Cation-dependent diastereomer switch was also observed in select examples.

  DOI：

  10.1021/jo049365i

文献信息

• [EN] HISTONE DEACETYLASE INHIBITORS AND COMPOSITIONS AND METHODS OF USE THEREOF<br/>[FR] INHIBITEURS D'HISTONE DÉSACÉTYLASE, ET COMPOSITIONS ET PROCÉDÉS POUR LES UTILISER
  申请人：CHDI FOUNDATION INC

  公开号：WO2012103008A1

  公开（公告）日：2012-08-02

  Provided are certain histone deacetylase (HDAC) inhibitors of Formula I, compositions thereof, and methods of their use.

  提供了某些Formula I的组蛋白去乙酰化酶（HDAC）抑制剂，以及它们的组合物和使用方法。
• HISTONE DEACETYLASE INHIBITORS AND COMPOSITIONS AND METHODS OF USE THEREOF
  申请人：Luckhurst Christopher A

  公开号：US20140163009A1

  公开（公告）日：2014-06-12

  Provided are certain histone deacetylase (HDAC) inhibitors of Formula I, compositions thereof, and methods of their use.

  提供了某些式I的组蛋白去乙酰化酶（HDAC）抑制剂，它们的组成物以及使用它们的方法。
• US9765054B2
  申请人：——

  公开号：US9765054B2

  公开（公告）日：2017-09-19
• Enhanced Diastereoselectivity via Confinement:  Photoisomerization of 2,3-Diphenylcyclopropane-1-carboxylic Acid Derivatives within Zeolites
  作者：J. Sivaguru、Raghavan. B. Sunoj、Takehiko Wada、Yumi Origane、Yoshihisa Inoue、Vaidhyanathan Ramamurthy

  DOI：10.1021/jo049365i

  日期：2004.10.1

  From the perspective of asymmetric induction, the photochemistry of 24 chiral esters and amides of cis-2,3-diphenylcyclopropane-1-carboxylic acid from excited singlet and triplet states has been investigated within zeolites. The chiral auxiliaries placed at a remote location from the isomerization site functioned far better within a zeolite than in solution. Generally, chiral auxiliaries with an aromatic or a carbonyl substituent performed better than the ones containing only alkyl substituents. A model based on cation-binding-dependent flexibility of the chiral auxiliary accounts for the observed variation in de between aryl (and carbonyl) and alkyl chiral auxiliaries within zeolites. Cation-dependent diastereomer switch was also observed in select examples.