(1S,2S,6R,7R,8R,10S)-4-(3-methoxyphenyl)-9-oxa-4-azatetracyclo[5.3.1.02,6.08,10]undecane-3,5-dione | 477248-69-4

• 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,8R,10S)-4-(3-methoxyphenyl)-9-oxa-4-azatetracyclo[5.3.1.02,6.08,10]undecane-3,5-dione
• CAS: 477248-69-4
• 化学式: C₁₆H₁₅NO₄
• 分子量: 285.299
• InChiKey: UETJQEMYERWAFW-LRRLDJKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.22
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.14
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,6R,7R,8R,10S)-4-(3-methoxyphenyl)-9-oxa-4-azatetracyclo[5.3.1.02,6.08,10]undecane-3,5-dione 在 硫酸 作用下， 反应 8.0h， 生成 2-exo-hydroxy-5-oxo-4-oxatricyclo[4.2.1.0^3,7]nonane-9-carboxylic acid
  参考文献：
  名称：

  摘要：

  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.

  DOI：

  10.1023/a:1015573902465
• 作为产物：
  描述：

  (1R,2S,6R,7S)-4-(3-Methoxy-phenyl)-4-aza-tricyclo[5.2.1.0^2,6]dec-8-ene-3,5-dione 在 过氧乙酸 作用下， 以 1,4-二氧六环 为溶剂， 以90%的产率得到(1S,2S,6R,7R,8R,10S)-4-(3-methoxyphenyl)-9-oxa-4-azatetracyclo[5.3.1.02,6.08,10]undecane-3,5-dione
  参考文献：
  名称：

  Spatial arrangement of norbornanedicarboxylic acids N-arylimides

  摘要：

  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.

  DOI：

  10.1134/s1070428010110023

文献信息

• 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.
• 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：——