N_b-tert-butoxycarbonyl-20-methylthio-N_a-demethyl-20-deethylsuaveolione | 841231-88-7

• 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: N_b-tert-butoxycarbonyl-20-methylthio-N_a-demethyl-20-deethylsuaveolione
• 英文别名: tert-butyl (1S,12S)-17-methylsulfanyl-3,15,20-triazapentacyclo[10.7.1.02,10.04,9.013,18]icosa-2(10),4,6,8,13,15,17-heptaene-20-carboxylate
• CAS: 841231-88-7
• 化学式: C₂₃H₂₅N₃O₂S
• 分子量: 407.536
• InChiKey: AMYSWAXCWRRLNX-OALUTQOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  83.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N_b-tert-butoxycarbonyl-20-methylthio-N_a-demethyl-20-deethylsuaveolione 在 镍 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以65%的产率得到N_b-tert-butoxycarbonyl-N_a-demethyl-20-deethylsuaveolione
  参考文献：
  名称：

  Synthesis of Na-Demethyl-20- deethylsuaveoline, the Struc- ture Proposed for Sellowiine

  摘要：

  A synthesis of N-a-demethyl-20-deethylsuaveoline (1), the structure assigned to the Rauwolfia alkaloid sellowiine, has been accomplished for the first time through a route using intramolecular oxazole-olefin Diels-Alder reaction. The H-1- and C-13-NMR spectral data and the specific rotation of the synthetic 1 were in disagreement with those reported for a natural sample, leaving the chemistry of this alkaloid incomplete.

  DOI：

  10.3987/com-04-10211
• 作为产物：
  描述：

  (1S,3S)-1,3,4,9-tetrahydro-3-(5-oxazolyl)-1-(2-oxoethyl)-2H-pyrido[3,4-b]indole-2-carboxylic acid 1,1-dimethylethyl ester 在 敌草腈 、 potassium tert-butylate 作用下， 以 xylene 、 苯 为溶剂， 反应 30.66h， 生成 N_b-tert-butoxycarbonyl-20-methylthio-N_a-demethyl-20-deethylsuaveolione
  参考文献：
  名称：

  Synthesis of Na-Demethyl-20- deethylsuaveoline, the Struc- ture Proposed for Sellowiine

  摘要：

  A synthesis of N-a-demethyl-20-deethylsuaveoline (1), the structure assigned to the Rauwolfia alkaloid sellowiine, has been accomplished for the first time through a route using intramolecular oxazole-olefin Diels-Alder reaction. The H-1- and C-13-NMR spectral data and the specific rotation of the synthetic 1 were in disagreement with those reported for a natural sample, leaving the chemistry of this alkaloid incomplete.

  DOI：

  10.3987/com-04-10211

文献信息

• Synthesis of Na-Demethyl-20- deethylsuaveoline, the Struc- ture Proposed for Sellowiine
  作者：Masashi Ohba、Itaru Natsutani

  DOI：10.3987/com-04-10211

  日期：——

  A synthesis of N-a-demethyl-20-deethylsuaveoline (1), the structure assigned to the Rauwolfia alkaloid sellowiine, has been accomplished for the first time through a route using intramolecular oxazole-olefin Diels-Alder reaction. The H-1- and C-13-NMR spectral data and the specific rotation of the synthetic 1 were in disagreement with those reported for a natural sample, leaving the chemistry of this alkaloid incomplete.