2,2,2-Trichloro-N-(4-cyano-cyclohex-3-enyl)-N-[2-(1H-indol-3-yl)-ethyl]-acetamide | 171367-16-1

• 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: 2,2,2-Trichloro-N-(4-cyano-cyclohex-3-enyl)-N-[2-(1H-indol-3-yl)-ethyl]-acetamide
• 英文别名: 2,2,2-trichloro-N-(4-cyanocyclohex-3-en-1-yl)-N-[2-(1H-indol-3-yl)ethyl]acetamide
• CAS: 171367-16-1
• 化学式: C₁₉H₁₈Cl₃N₃O
• 分子量: 410.73
• InChiKey: DFSHVVVJNXMWLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  59.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2,2-Trichloro-N-(4-cyano-cyclohex-3-enyl)-N-[2-(1H-indol-3-yl)-ethyl]-acetamide 在 偶氮二异丁腈 、 三(三甲基硅基)硅烷 、 三正丁基氢锡 作用下， 生成 (1RS,5SR,6SR)-2-[2-(3-indolyl)ethyl]-3-oxo-2-azabicyclo[3.3.1]nonane-6-carbonitrile
  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：

  2,2,2-trichloro-N-[2-(1H-indol-3-yl)ethyl]-N-(4-oxocyclohexyl)acetamide 在 吡啶 、 盐酸 、 zinc(II) iodide 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 2,2,2-Trichloro-N-(4-cyano-cyclohex-3-enyl)-N-[2-(1H-indol-3-yl)-ethyl]-acetamide
  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.