| 201225-08-3

• 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
• CAS: 201225-08-3
• 化学式: C₂₀H₂₃Cl₃N₂O₃
• 分子量: 445.773
• InChiKey: WXRXZUWFSFASIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  54.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以85%的产率得到2,2,2-trichloro-N-[2-(1H-indol-3-yl)ethyl]-N-(4-oxocyclohexyl)acetamide
  参考文献：
  名称：

  First total synthesis of (±)-melinonine-E

  摘要：

  首次合成了生物碱 Melinonine-E，其关键步骤是通过自由基环化法合成 2-氮杂双环[3.3.l]壬烷核、氰基环化至轴向位置以及通过比施勒-纳皮拉尔斯基环化法封闭 C 环。

  DOI：

  10.1039/c39950002141
• 作为产物：
  描述：

  1,4-环己二酮单乙二醇缩酮 在 吡啶 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 36.0h， 生成
  参考文献：
  名称：

  First Total Synthesis of (±)-Melinonine-E and (±)-Strychnoxanthine Using a Radical Cyclization Process as the Core Ring-Forming Step

  摘要：

  The first total synthesis of (+/-)-melinonine-E and (+/-)-strychnoxanthine is described. The key common step for the synthesis of both alkaloids is the elaboration of the 8-azabicyclo[3.3.1]nonane nucleus (D and E rings) by a radical carbocyclization, using an alpha-carbamoyldichloromethyl radical as a donor. The closure of the C ring by a Bischler-Napieralski cyclization, followed by an epimerization process to gain the axial nitrile 20, and appropriate reduction transformations afforded pentacyclic alcohol 23. This alcohol was converted into either (+/-)-melinonine-E (1) or (+/-)-strychnoxanthine (2) by means of a palladium black dehydrogenation of the C ring or a SeO2 oxidation of the corresponding acetate 25, respectively.

  DOI：

  10.1021/jo971148c

文献信息

• First total synthesis of (±)-melinonine-E
  作者：Josefina Quirante、Carmen Escolano、Joan Bosch、Josep Bonjoch

  DOI：10.1039/c39950002141

  日期：——

  The alkaloid melinonine-E has been synthesised for the first time, the key steps being the elaboration of the 2-azabicyclo[3.3.l]nonane nucleus by a radical cyclisation, the epimerisation of the cyano group to an axial position, and the closure of the C ring by Bischler–Napieralski cyclisation.

  首次合成了生物碱 Melinonine-E，其关键步骤是通过自由基环化法合成 2-氮杂双环[3.3.l]壬烷核、氰基环化至轴向位置以及通过比施勒-纳皮拉尔斯基环化法封闭 C 环。
• First Total Synthesis of (±)-Melinonine-E and (±)-Strychnoxanthine Using a Radical Cyclization Process as the Core Ring-Forming Step
  作者：Josefina Quirante、Carmen Escolano、Alma Merino、Josep Bonjoch

  DOI：10.1021/jo971148c

  日期：1998.2.1

  The first total synthesis of (+/-)-melinonine-E and (+/-)-strychnoxanthine is described. The key common step for the synthesis of both alkaloids is the elaboration of the 8-azabicyclo[3.3.1]nonane nucleus (D and E rings) by a radical carbocyclization, using an alpha-carbamoyldichloromethyl radical as a donor. The closure of the C ring by a Bischler-Napieralski cyclization, followed by an epimerization process to gain the axial nitrile 20, and appropriate reduction transformations afforded pentacyclic alcohol 23. This alcohol was converted into either (+/-)-melinonine-E (1) or (+/-)-strychnoxanthine (2) by means of a palladium black dehydrogenation of the C ring or a SeO2 oxidation of the corresponding acetate 25, respectively.