(1R,2R)-1-phenylthio-2-[N-(3,5-dinitrobenzoyl)amino]cyclopentane | 1174458-59-3

• 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-dinitrobenzoyl)amino]cyclopentane
• 英文别名: 3,5-dinitro-N-[(1R,2R)-2-phenylsulfanylcyclopentyl]benzamide
• CAS: 1174458-59-3
• 化学式: C₁₈H₁₇N₃O₅S
• 分子量: 387.416
• InChiKey: ZJTROJKCMXDECE-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  苯基硫三甲基硅烷 、 6-Azabicyclo[3.1.0]hexan-6-yl-(3,5-dinitrophenyl)methanone 在 (R)-VAPOL calcium phosphate 、 magnesium(II) (R)-2,2'-diphenyl-3,3'-biphenanthryl-4,4'-diyl phosphate 作用下， 以 三氯乙烷 为溶剂， 反应 4.0h， 以98%的产率得到(1R,2R)-1-phenylthio-2-[N-(3,5-dinitrobenzoyl)amino]cyclopentane
  参考文献：
  名称：

  Studies on the true catalyst in the phosphate-promoted desymmetrization of meso-aziridines with silylated nucleophiles

  摘要：

  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.

  DOI：

  10.1016/j.tet.2012.10.068

文献信息

• 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.
• 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.