(1S,2S,6R,7R)-4-(3-Methoxy-phenyl)-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (1S,2S,6R,7R)-4-(3-Methoxy-phenyl)-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione
• 英文别名: (1R,2R,6S,7S)-4-(3-methoxyphenyl)-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: UPLCBKNQKQHXOV-DHPDLVEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2S,6R,7R)-4-(3-Methoxy-phenyl)-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 在 硫酸 、 双氧水 、 溶剂黄146 、 水 作用下， 以 水 为溶剂， 反应 3.0h， 以86%的产率得到
  参考文献：
  名称：

  Stereochemistry of dihydroxylation of N-arylbicyclo[2.2.1]-hept-5-ene-endo- and -exo-2,3-dicarboximides

  摘要：

  Stereochemistry of the oxidation of N-arylbicyclo[2.2.1]hept-5-ene-endo-and-exo-2,3-dicarboximides at the double bond with peroxyacetic acid generated in situ in the presence of sulfuric acid and with an anhydrous dioxane solution of peroxyacetic acid was studied. In both cases, the reaction was stereospecific, regardless of the substituent in the N-aryl group and configuration of the imide ring, but the reaction direction depended on the presence of water in the system. In the first case, the corresponding trans-5,6-dihydroxy derivatives were formed, while in the second, exo-5,6-epoxy derivatives. The oxidation of N-arylbicyclo[2.2.1]-hept-5-ene-endo-and-exo-2,3-dicarboximides with a solution of potassium permanganate in aqueous acetone gave the corresponding N-aryl-cis-5,6-dihydroxybicyclo[2.2.1]heptane-endo-and-exo-2,3-dicarboximides. The exo,cis,exo and exo,cis,endo configurations of the synthesized compounds were determined by H-1 NMR spectroscopy.

  DOI：

  10.1134/s1070428007110097
• 作为产物：
  描述：

  纳迪克酸酐 、 间氨基苯甲醚 生成 (1S,2S,6R,7R)-4-(3-Methoxy-phenyl)-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione
  参考文献：
  名称：

  SALAXOV, M. S.;BAGMANOV, B. T.;MUSAEVA, N. F.;NAGIEV, V. A., VINITI 1111-84

  摘要：

  DOI：

文献信息

• ——
  作者：M. S. Salakhov、M. I. Bagmanova

  DOI：10.1023/a:1015573902465

  日期：——

  Epoxidation of endo- and evo-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid N-arylimides with a solution of peracetic acid in anhydrous dioxane affords 5,6-exo-epoxybicycloheptanedicarboxylic acid N-arylimides. The epoxidation reaction is not sensitive to the configuration of the imide fragment, to the character and position of the substituent in the aromatic ring. The reaction is determined only by oxidation conditions.
• Spatial arrangement of norbornanedicarboxylic acids N-arylimides
  作者：M. S. Salakhov、B. T. Bagmanov、N. S. Nabiev

  DOI：10.1134/s1070428010110023

  日期：2010.11

  The effect of substituents on the spatial arrangement of norbornane compounds was investigated. Norbornanedicarboxylic acids N-arylimides with OCH(3), Cl, NO(2) groups in the ortho-position of the aromatic ring form as conformational isomers with hindered rotation. The specific spatial isomerism is confirmed by the quantum-chemical calculations.
• MUSAEVA N. F.;SALAXOV M. S.;NAGIEV V. A.;SULEJMANOV S. N., I-HT XLORORGAN SINTEZA AN AZSSR, SUMGAIT, 1984. 8 S BIBLIOGR. 11 NAZV. (R+
  作者：MUSAEVA N. F.、SALAXOV M. S.、NAGIEV V. A.、SULEJMANOV S. N.

  DOI：——

  日期：——
• SALAXOV M. S.; BAGMANOV B. T.; NAGIEV V. A., IN-T XLORORGAN. SINTEZA AN AZSSR, SUMGAIT,(1986) 12 S., IL., VINITI , 862+
  作者：SALAXOV M. S.、 BAGMANOV B. T.、 NAGIEV V. A.

  DOI：——

  日期：——
• Stereochemistry of dihydroxylation of N-arylbicyclo[2.2.1]-hept-5-ene-endo- and -exo-2,3-dicarboximides
  作者：B. T. Bagmanov

  DOI：10.1134/s1070428007110097

  日期：2007.11

  Stereochemistry of the oxidation of N-arylbicyclo[2.2.1]hept-5-ene-endo-and-exo-2,3-dicarboximides at the double bond with peroxyacetic acid generated in situ in the presence of sulfuric acid and with an anhydrous dioxane solution of peroxyacetic acid was studied. In both cases, the reaction was stereospecific, regardless of the substituent in the N-aryl group and configuration of the imide ring, but the reaction direction depended on the presence of water in the system. In the first case, the corresponding trans-5,6-dihydroxy derivatives were formed, while in the second, exo-5,6-epoxy derivatives. The oxidation of N-arylbicyclo[2.2.1]-hept-5-ene-endo-and-exo-2,3-dicarboximides with a solution of potassium permanganate in aqueous acetone gave the corresponding N-aryl-cis-5,6-dihydroxybicyclo[2.2.1]heptane-endo-and-exo-2,3-dicarboximides. The exo,cis,exo and exo,cis,endo configurations of the synthesized compounds were determined by H-1 NMR spectroscopy.