4-nitro-N-[(1R,2R)-2-(phenylthio)cyclohexyl]benzamide | 1161834-72-5

• 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: 4-nitro-N-[(1R,2R)-2-(phenylthio)cyclohexyl]benzamide
• 英文别名: (1R,2R)-1-phenylthio-2-[N-(4-nitrobenzoyl)amino]cyclohexane；4-nitro-N-(2-(phenylthio)cyclohexyl)benzamide；4-nitro-N-[(1R,2R)-2-phenylsulfanylcyclohexyl]benzamide
• CAS: 1161834-72-5
• 化学式: C₁₉H₂₀N₂O₃S
• 分子量: 356.445
• InChiKey: FQKFNAUQMWPUMU-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯基硫三甲基硅烷 、 7-(4-nitrobenzoyl)-7-azabicyclo<4.1.0>heptane 在 (R)-VAPOL 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 (1S,2S)-1-phenylthio-2-[N-(4-nitrobenzoyl)amino]cyclohexane 、 4-nitro-N-[(1R,2R)-2-(phenylthio)cyclohexyl]benzamide
  参考文献：
  名称：

  Highly Enantioselective Synthesis of β-Amidophenylthioethers by Organocatalytic Desymmetrization of meso-Aziridines

  摘要：

  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.

  DOI：

  10.1021/ol901209n

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。
• Desymmetrization of meso-N-Acylaziridines with Benzenethiols Promoted by α,α-Diaryl-L-prolinols
  作者：Alessandra Lattanzi、Giorgio Della Sala

  DOI：10.1002/ejoc.200900095

  日期：——

  α,α-Diaryl-L-prolinols were disclosed to promote the desymmetrization of meso-N-acylaziridines with benzenethiols to afford the products in good yields and moderate enantioselectivities (up to 61 % ee), which can be greatly improved to >90 % ee after a single recrystallization. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  公开了 α,α-二芳基-L-脯氨醇以促进内消旋-N-酰基氮丙啶与苯硫醇的去对称化，从而以良好的收率和适中的对映选择性（高达 61 % ee）提供产品，可以大大提高到 > 90 % ee 单次重结晶后。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Chiral Phosphoric Acid-Catalyzed Desymmetrization of <i>meso</i>-Aziridines with Functionalized Mercaptans
  作者：Shawn E. Larson、Juan C. Baso、Guilong Li、Jon C. Antilla

  DOI：10.1021/ol902123h

  日期：2009.11.19

  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.