(1R,2R)-1-phenylseleno-2-[N-(3,5-dinitrobenzoyl)amino]cyclohexane | 1415893-18-3

• 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-phenylseleno-2-[N-(3,5-dinitrobenzoyl)amino]cyclohexane
• 英文别名: 3,5-dinitro-N-[(1R,2R)-2-phenylselanylcyclohexyl]benzamide
• CAS: 1415893-18-3
• 化学式: C₁₉H₁₉N₃O₅Se
• 分子量: 448.337
• InChiKey: VNJQWFLRVVOSTO-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.99
• 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：
  121
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1-phenylseleno-2-[N-(3,5-dinitrobenzoyl)amino]cyclohexane 在 苯基溴化硒 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以88%的产率得到(3aR,7aS)-2-(3,5-dinitrophenyl)-3a,4,5,6,7,7a-hexahydro-1,3-benzoxazole
  参考文献：
  名称：

  A general phosphoric acid-catalyzed desymmetrization of meso-aziridines with silylated selenium nucleophiles

  摘要：

  首次报道了硒亲核试剂参与的中位氮杂环丙烷去对称化反应。该反应以VAPOL磷酸氢二钠为促进剂，采用（苯硒基）三甲基硅烷作为亲核试剂，其适用范围非常广泛，且具有高度的对映选择性（84-99% 对映体过量）。

  DOI：

  10.1039/c1ob05837a
• 作为产物：
  描述：

  7-(3,5-dinitrobenzoyl)-7-azabicyclo[4.1.0]heptane 、 三甲基苯基硒硅烷 在 (R)-VAPOL calcium phosphate 、 magnesium(II) (R)-2,2'-diphenyl-3,3'-biphenanthryl-4,4'-diyl phosphate 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以90%的产率得到(1R,2R)-1-phenylseleno-2-[N-(3,5-dinitrobenzoyl)amino]cyclohexane
  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