(4aR,10bS,11R)-10,11-epoxy-1,2,3,4,5,6-hexahydro-9-methoxy-3-methyl-4a,10b-propanobenzoisoquinolin-12-one dimethyl acetal | 142467-30-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: (4aR,10bS,11R)-10,11-epoxy-1,2,3,4,5,6-hexahydro-9-methoxy-3-methyl-4a,10b-propanobenzoisoquinolin-12-one dimethyl acetal
• 英文别名: (1R,4R,12S)-3,3,7-trimethoxy-15-methyl-5-oxa-15-azapentacyclo[8.6.2.01,12.04,12.06,11]octadeca-6,8,10-triene
• CAS: 142467-30-9
• 化学式: C₂₀H₂₇NO₄
• 分子量: 345.439
• InChiKey: HGECGFMMKNSRBP-QYZOEREBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4aR,10bS,11R)-10,11-epoxy-1,2,3,4,5,6-hexahydro-9-methoxy-3-methyl-4a,10b-propanobenzoisoquinolin-12-one dimethyl acetal 在 盐酸 作用下， 反应 0.33h， 以91%的产率得到(4aR,10bS,11R)-10,11-epoxy-1,2,3,4,5,6-hexahydro-9-methoxy-3-methyl-4a,10b-propanobenzoisoquinolin-12-one
  参考文献：
  名称：

  10,11-Epoxy-3-methyl-1,2,3,4-tetrahydro-4a,10b-propanobenzo[f]isoquinolin-12-ones: A Novel Type of Opioid Analgesics — Synthetic Approach and Structure Elucidation

  摘要：

  The title compounds were obtained by nucleophilic cyclopropane ring opening and intramolecular Hofmann reactions, starting from 7,14-cyclo-dihydrocodeinone (1). An X-ray analysis of 10,11-epoxy-9-methoxy-3-methyl-1,2,3,4-tetrahydro-4a,10b-propanobenzo[f]isoquinolin-12-one dimethyl acetal (3) was performed as basis of molecular modeling studies.

  DOI：

  10.3987/com-91-5855
• 作为产物：
  描述：

  (4R,4aS,6aR,11bR)-4a-(chloromethyl)-6,6,8-trimethoxy-3-methyl-1,2,3,4,4a,5,6,6a-octahydro-4,11-methanobenzofuro[3',2':2,3]cyclopenta[1,2-c]pyridine 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 14.0h， 生成 (4aR,10bS,11R)-10,11-epoxy-1,2,3,4,5,6-hexahydro-9-methoxy-3-methyl-4a,10b-propanobenzoisoquinolin-12-one dimethyl acetal
  参考文献：
  名称：

  10,11-Epoxy-3-methyl-1,2,3,4-tetrahydro-4a,10b-propanobenzo[f]isoquinolin-12-ones: A Novel Type of Opioid Analgesics — Synthetic Approach and Structure Elucidation

  摘要：

  The title compounds were obtained by nucleophilic cyclopropane ring opening and intramolecular Hofmann reactions, starting from 7,14-cyclo-dihydrocodeinone (1). An X-ray analysis of 10,11-epoxy-9-methoxy-3-methyl-1,2,3,4-tetrahydro-4a,10b-propanobenzo[f]isoquinolin-12-one dimethyl acetal (3) was performed as basis of molecular modeling studies.

  DOI：

  10.3987/com-91-5855