8,9,10-trimethoxy-2,3,6,10b-tetrahydro-1H-pyrrolo[2,1-a]isoquinolin-5-one | 1161236-47-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 8,9,10-trimethoxy-2,3,6,10b-tetrahydro-1H-pyrrolo[2,1-a]isoquinolin-5-one
• CAS: 1161236-47-0
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: MIRFXQACYGRRMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8,9,10-trimethoxy-2,3,6,10b-tetrahydro-1H-pyrrolo[2,1-a]isoquinolin-5-one 在 lithium aluminium tetrahydride 、 三乙胺盐酸盐 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到8,9,10-trimethoxy-1,2,3,5,6,10b-hexahydro-pyrrolo[2,1-a]isoquinoline
  参考文献：
  名称：

  Efficient Syntheses of Crispine A and Harmicine by Rh-Catalyzed Cyclohydrocarbonylation

  摘要：

  The first examples of Rh-catalyzed cyclohydrocarbonylation-bicyclization of N-allylic amides of arylacetic acids are reported. This novel carbonylative bicyclization process was successfully applied to the rapid syntheses of crispine A and its analogues (tricyclic indolizidine alkaloids) as well as harmicine (tetracyclic beta-carboline alkaloid).

  DOI：

  10.1021/ol900702t
• 作为产物：
  描述：

  一氧化碳 、 N-烯丙基-2-(3,4,5-三甲氧基苯基)乙酰胺 在 Rh(acac)2(CO)2 、 氢气 、 对甲苯磺酸 、 溶剂黄146 、 6,6′-[(3,3′-二叔丁基-5,5′-二甲氧基-1,1′-二苯基-2,2′-二基)双(氧)]双(二苯并[d,f][1,3,2]二噁磷杂庚英) 作用下， 60.0 ℃ 、405.33 kPa 条件下， 反应 16.0h， 以83%的产率得到8,9,10-trimethoxy-2,3,6,10b-tetrahydro-1H-pyrrolo[2,1-a]isoquinolin-5-one
  参考文献：
  名称：

  Efficient Syntheses of Crispine A and Harmicine by Rh-Catalyzed Cyclohydrocarbonylation

  摘要：

  The first examples of Rh-catalyzed cyclohydrocarbonylation-bicyclization of N-allylic amides of arylacetic acids are reported. This novel carbonylative bicyclization process was successfully applied to the rapid syntheses of crispine A and its analogues (tricyclic indolizidine alkaloids) as well as harmicine (tetracyclic beta-carboline alkaloid).

  DOI：

  10.1021/ol900702t

文献信息

• Efficient Syntheses of Crispine A and Harmicine by Rh-Catalyzed Cyclohydrocarbonylation
  作者：Wen-Hua Chiou、Gau-Hong Lin、Che-Cheng Hsu、Stephen J. Chaterpaul、Iwao Ojima

  DOI：10.1021/ol900702t

  日期：2009.6.18

  The first examples of Rh-catalyzed cyclohydrocarbonylation-bicyclization of N-allylic amides of arylacetic acids are reported. This novel carbonylative bicyclization process was successfully applied to the rapid syntheses of crispine A and its analogues (tricyclic indolizidine alkaloids) as well as harmicine (tetracyclic beta-carboline alkaloid).