3,5-dinitro-N-[(1R,2R)-2-(phenylthio)cyclohexyl]benzamide | 1161834-76-9

• 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: 3,5-dinitro-N-[(1R,2R)-2-(phenylthio)cyclohexyl]benzamide
• 英文别名: (1R,2R)-1-phenylthio-2-[N-(3,5-dinitrobenzoyl)amino]cyclohexane；3,5-dinitro-N-(2-(phenylthio)cyclohexyl)benzamide；3,5-dinitro-N-[(1R,2R)-2-phenylsulfanylcyclohexyl]benzamide
• CAS: 1161834-76-9
• 化学式: C₁₉H₁₉N₃O₅S
• 分子量: 401.443
• InChiKey: JQKICDIEQHLFPM-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 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：
  146
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  7-(3,5-dinitrobenzoyl)-7-azabicyclo[4.1.0]heptane 、 苯基硫三甲基硅烷 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 1.0h， 以95%的产率得到3,5-dinitro-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)
• Gram-Scale Preparation of VAPOL Hydrogenphosphate: A Structurally Distinct Chiral Brønsted Acid
  作者：William Wulff、Aman Desai、Li Huang、Gerald Rowland、Jon Antilla

  DOI：10.1055/s-0029-1218783

  日期：2010.6

  A detailed gram-scale synthesis of VAPOL hydrogenphosphate, a structurally distinct chiral Brønsted acid, is presented. The reaction utilizes commercially available starting materials, proceeds with high yields and has been reproduced numerous times at scale.

  本文详细介绍了VAPOL磷酸氢盐的克级合成，这是一种结构独特的布伦斯特手性酸。该反应利用市售的原料，收率高，并已多次大规模复制。
• 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.
• Studies on the true catalyst in the phosphate-promoted desymmetrization of meso-aziridines with silylated nucleophiles
  作者：Giorgio Della Sala

  DOI：10.1016/j.tet.2012.10.068

  日期：2013.1

  Significant amounts of metal phosphate impurities have been detected by NMR spectroscopy and ICP-OES analysis of synthetic, as well as purchased, samples of VAPOL hydrogen phosphate purified on silica gel. The previously reported VAPOL hydrogen phosphate-catalyzed desymmetrization of meso-aziridines with different silylated compounds, has been re-examined. While metal-free phosphoric acid exhibited low activity and enantioselectivity, calcium and magnesium phosphate salts proved to be the true catalysts in these related processes. Reproducible high enantioselectivities were obtained in the ring-opening of cyclic meso-aziridines with Me3SiX (X=SPh, SePh, N-3) employing a 1:1 mixture of calcium and magnesium VAPOL phosphates. The reaction has been successfully extended to Me3SiSBn, Me3SiSMe and Me3SiNCS, giving ring-opened products in high yield and unprecedented moderate to good enantioselectivities. (C) 2012 Elsevier Ltd. All rights reserved.