3-hydroxy-2,12-dimethoxy-5,6,7,8,9,10,11,14-octahydrodibenz[d,f]azecine | 250687-97-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-hydroxy-2,12-dimethoxy-5,6,7,8,9,10,11,14-octahydrodibenz[d,f]azecine
• 英文别名: 4,16-Dimethoxy-10-azatricyclo[12.4.0.02,7]octadeca-1(14),2,4,6,16-pentaen-5-ol
• CAS: 250687-97-9
• 化学式: C₁₉H₂₅NO₃
• 分子量: 315.412
• InChiKey: STNLTBCSWFGFRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-hydroxy-2,12-dimethoxy-5,6,7,8,9,10,11,14-octahydrodibenz[d,f]azecine 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.33h， 以26%的产率得到17-hydroxy-16-methoxy-8,9,11,12-tetrahydro-7H-cyclohexa[a]pyrrolo[2,1-b][3]benzazepin-2-one
  参考文献：
  名称：

  Convenient Synthesis of Cyclohexa[a]pyrrolo[2,1-b][3]benzazepine, a Cephalotaxus Alkaloid Analogue

  摘要：

  Irradiation of N-(3-hydroxy-4-methoxyphenethyl) -3-(2-iodo-5-methoxyphenyl)propionamide (11) in methanol in the presence of sodium hydroxide furnished 3-hydroxy-2,12-dimethoxy-6,7,9,10-tetrahydrodibenz[d3]azecin-8(5H)-one (14) which was successfully led to cephalotaxine analogue (17) bearing pyrrolo[2,1-b][3]benzazepine skeleton by reduction with borane followed by Birch reduction and subsequent acidic treatment. The structure of 17 was established by means of X-Ray crystallography.

  DOI：

  10.3987/com-99-8643
• 作为产物：
  描述：

  2-(3-(苄氧基)-4-甲氧基苯基)乙胺 在 sodium hydroxide 、 硼烷四氢呋喃络合物 、 甲烷磺酸 、 茴香硫醚 、 氨 、 sodium 作用下， 以 四氢呋喃 、 甲醇 、 三氟乙酸 、 xylene 为溶剂， 反应 12.0h， 生成 3-hydroxy-2,12-dimethoxy-5,6,7,8,9,10,11,14-octahydrodibenz[d,f]azecine
  参考文献：
  名称：

  Convenient Synthesis of Cyclohexa[a]pyrrolo[2,1-b][3]benzazepine, a Cephalotaxus Alkaloid Analogue

  摘要：

  Irradiation of N-(3-hydroxy-4-methoxyphenethyl) -3-(2-iodo-5-methoxyphenyl)propionamide (11) in methanol in the presence of sodium hydroxide furnished 3-hydroxy-2,12-dimethoxy-6,7,9,10-tetrahydrodibenz[d3]azecin-8(5H)-one (14) which was successfully led to cephalotaxine analogue (17) bearing pyrrolo[2,1-b][3]benzazepine skeleton by reduction with borane followed by Birch reduction and subsequent acidic treatment. The structure of 17 was established by means of X-Ray crystallography.

  DOI：

  10.3987/com-99-8643

文献信息

• Convenient Synthesis of Cyclohexa[a]pyrrolo[2,1-b][3]benzazepine, a Cephalotaxus Alkaloid Analogue
  作者：Hitoshi Tanaka、Mitsunobu Doi、Hiroshi Shimizu、Hideo Etoh

  DOI：10.3987/com-99-8643

  日期：——

  Irradiation of N-(3-hydroxy-4-methoxyphenethyl) -3-(2-iodo-5-methoxyphenyl)propionamide (11) in methanol in the presence of sodium hydroxide furnished 3-hydroxy-2,12-dimethoxy-6,7,9,10-tetrahydrodibenz[d3]azecin-8(5H)-one (14) which was successfully led to cephalotaxine analogue (17) bearing pyrrolo[2,1-b][3]benzazepine skeleton by reduction with borane followed by Birch reduction and subsequent acidic treatment. The structure of 17 was established by means of X-Ray crystallography.