(1R,5R,6S)-7,7-dichloro-5-methyl-2-azabicyclo[4.1.0]heptan-3-one | 586398-81-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: (1R,5R,6S)-7,7-dichloro-5-methyl-2-azabicyclo[4.1.0]heptan-3-one
• CAS: 586398-81-4
• 化学式: C₇H₉Cl₂NO
• 分子量: 194.061
• InChiKey: BSFLSOHSEYOYFQ-PQLUHFTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.31
• 重原子数：
  11.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (1R,5R,6S)-7,7-dichloro-5-methyl-2-azabicyclo[4.1.0]heptan-3-one 在 triethyloxonium fluoroborate 、 氨 作用下， 以 二氯甲烷 、 乙醇 为溶剂， 生成 (1R,5R,6S)-7,7-dichloro-5-methyl-2-azabicyclo[4.1.0]hept-2-en-3-amine
  参考文献：
  名称：

  Design and Synthesis of Orally Bioavailable Inhibitors of Inducible Nitric Oxide Synthase. Identification of 2-Azabicyclo[4.1.0]heptan-3-imines

  摘要：

  Further chemical modification of 2-iminopiperidines fused to cyclopropane rings was performed. Optically active isomers 2 and 13 were synthesized and their biological activity was evaluated. Compound 2 exhibited greater potency and more isoform selectivity than enantiomer 13 in the iNOS inhibition assay. One of the gem-chlorines on the fused cyclopropane moiety of 2 was eliminated to produce 3, which showed reduced potency for iNOS inhibition, as well as 4 with an increased potency. The isoform selectivity of 4 was also much higher than that of 3. This was also true for the corresponding methyl derivatives 6-9. The structure-activity relationship (SAR) study and computer aided docking study of the most optimized structure 4 with human iNOS will also be reported. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00034-8
• 作为产物：
  描述：

  (4R)-1-(4-methoxybenzyl)-4-methyl-3,4-dihydropyridin-2-one 在 sodium hydroxide 、 三氟化硼乙醚 、 甲基三辛基氯化铵 作用下， 以 苯甲醚 为溶剂， 生成 (1R,5R,6S)-7,7-dichloro-5-methyl-2-azabicyclo[4.1.0]heptan-3-one
  参考文献：
  名称：

  Design and Synthesis of Orally Bioavailable Inhibitors of Inducible Nitric Oxide Synthase. Identification of 2-Azabicyclo[4.1.0]heptan-3-imines

  摘要：

  Further chemical modification of 2-iminopiperidines fused to cyclopropane rings was performed. Optically active isomers 2 and 13 were synthesized and their biological activity was evaluated. Compound 2 exhibited greater potency and more isoform selectivity than enantiomer 13 in the iNOS inhibition assay. One of the gem-chlorines on the fused cyclopropane moiety of 2 was eliminated to produce 3, which showed reduced potency for iNOS inhibition, as well as 4 with an increased potency. The isoform selectivity of 4 was also much higher than that of 3. This was also true for the corresponding methyl derivatives 6-9. The structure-activity relationship (SAR) study and computer aided docking study of the most optimized structure 4 with human iNOS will also be reported. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00034-8