(+/-)-20-epinorisodasycarpidone | 95588-59-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (+/-)-20-epinorisodasycarpidone
• 英文别名: (+/-)-Norisodasycarpidone；N-demethylepiisodasycarpidone；(1R,12R,13S)-13-ethyl-9,15-diazatetracyclo[10.3.1.02,10.03,8]hexadeca-2(10),3,5,7-tetraen-11-one
• CAS: 95588-59-3
• 化学式: C₁₆H₁₈N₂O
• 分子量: 254.332
• InChiKey: ODEWHVMZOXJSBX-IRUJWGPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1RS,4RS,5SR)-4-Ethyl-1,2,3,4,5,6-hexahydro-1,5-methanoazocino<4,3-b>indole 在 selenium(IV) oxide 、 二甲基硫 、 三氟化硼乙醚 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 氯仿 为溶剂， 反应 44.5h， 生成 (+/-)-20-epinorisodasycarpidone
  参考文献：
  名称：

  Total Synthesis of Uleine-Type and Strychnos Alkaloids through a Common Intermediate

  摘要：

  A stereoselective total synthesis of the alkaloids of the uleine group, dasycarpidone, dasycarpidol, and nordasycarpidone, has been accomplished from the tetracyclic intermediate 1, which has been prepared by two alternative routes, either by Fischer indolization of 2-azabicyclo[3.3.1]nonanone 9 or, more efficiently, by stereocontrolled cyclization of 2-[(2-cyano-3-ethyl-4-piperidyl)methyl]i 24a and 24b. From the same tetracyclic intermediate 1, the Strychnos alkaloid tubotaiwine was also synthesized, the key step being the construction of the quaternary spiranic center by cyclization of a thionium ion upon the indole beta-position.

  DOI：

  10.1021/jo00093a028

文献信息

• Studies on the Configurational Stability of 3-(2-Piperidyl)indoles
  作者：Mercedes Amat、Sabine Hadida、Núria Llor、Swargam Sathyanarayana、Joan Bosch

  DOI：10.1021/jo952251+

  日期：1996.1.1
• Synthetic applications of 2-cyano-1,2,3,6-tetrahydropyridines. 2. Synthesis of isodasycarpidone and related systems, the ervitsine skeleton and its benzo analog
  作者：Joan Bosch、Mario Rubiralta、Antonio Domingo、Jordi Bolos、Ana Linares、Cristina Minguillon、Mercedes Amat、Josep Bonjoch

  DOI：10.1021/jo00209a031

  日期：1985.5
• Total Synthesis of Uleine-Type and Strychnos Alkaloids through a Common Intermediate
  作者：Jordi Gracia、Nuria Casamitjana、Josep Bonjoch、Joan Bosch

  DOI：10.1021/jo00093a028

  日期：1994.7

  A stereoselective total synthesis of the alkaloids of the uleine group, dasycarpidone, dasycarpidol, and nordasycarpidone, has been accomplished from the tetracyclic intermediate 1, which has been prepared by two alternative routes, either by Fischer indolization of 2-azabicyclo[3.3.1]nonanone 9 or, more efficiently, by stereocontrolled cyclization of 2-[(2-cyano-3-ethyl-4-piperidyl)methyl]i 24a and 24b. From the same tetracyclic intermediate 1, the Strychnos alkaloid tubotaiwine was also synthesized, the key step being the construction of the quaternary spiranic center by cyclization of a thionium ion upon the indole beta-position.