(1R,2R)-1-phenylthio-2-[N-(3,5-bis-trifluoromethylbenzoyl)amino]cyclohexane | 1174458-58-2

• 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: (1R,2R)-1-phenylthio-2-[N-(3,5-bis-trifluoromethylbenzoyl)amino]cyclohexane
• 英文别名: N-(2-(phenylthio)cyclohexyl)-3,5-bis(trifluoromethyl)benzamide；N-[(1R,2R)-2-phenylsulfanylcyclohexyl]-3,5-bis(trifluoromethyl)benzamide
• CAS: 1174458-58-2
• 化学式: C₂₁H₁₉F₆NOS
• 分子量: 447.444
• InChiKey: JLYYNQPQJYSUCE-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  7-(3,5-bis-trifluoromethylbenzoyl)-7-azabicyclo[4.1.0]heptane 、 苯硫酚 在 苯膦酸 作用下， 生成 (1R,2R)-1-phenylthio-2-[N-(3,5-bis-trifluoromethylbenzoyl)amino]cyclohexane
  参考文献：
  名称：

  Chiral Phosphoric Acid-Catalyzed Desymmetrization of meso-Aziridines with Functionalized Mercaptans

  摘要：

  Conditions for the phosphoric acid-catalyzed highly enantioselective ring-opening of meso-aziridines with a series of functionalized aromatic thiol nucleophiles are described. The procedure utilizes commercially available aromatic thiols, a series of meso-aziridines, and a catalytic amount of VAPOL phosphoric acid to explore the substrate scope of this highly enantioselective reaction.

  DOI：

  10.1021/ol902123h

文献信息

• Guanidine-catalyzed enantioselective desymmetrization of meso-aziridines
  作者：Yan Zhang、Choon Wee Kee、Richmond Lee、Xiao Fu、Julian Ying-Teck Soh、Esther Mun Foong Loh、Kuo-Wei Huang、Choon-Hong Tan

  DOI：10.1039/c0cc05840h

  日期：——

  An amino-indanol derived chiral guanidine was developed as an efficient Brønsted base catalyst for the desymmetrization of meso-aziridines with both thiols and carbamodithioic acids as nucleophiles, which provided 1,2-difunctionalized ring-opened products in high yields and enantioselectivities.

  一种氨基-吲哚衍生的手性胍被开发作为高效的Brønsted碱催化剂，用于与硫醇和氨基二硫酸作为核苷酸的meso-亚胺环的去对称化，提供高产率和对映选择性的1,2-双功能化开环产物。
• Highly Enantioselective Synthesis of β-Amidophenylthioethers by Organocatalytic Desymmetrization of <i>meso</i>-Aziridines
  作者：Giorgio Della Sala、Alessandra Lattanzi

  DOI：10.1021/ol901209n

  日期：2009.8.6

  The desymmetrization of N-acylaziridines with Me3SiSPh, catalyzed by commercially available (R) and (S)-VAPOL hydrogen phosphate, produced beta-(N-acylamino)phenylthioethers in a highly enantioselective and efficient manner (78-99% ee). The selection of the suitable aziridine/nucleophile/catalyst molar ratio is crucial to obtain high ee's.