3-{2-[(2-Chloro-acetyl)-(4-oxo-cyclohexyl)-amino]-ethyl}-indole-1-carboxylic acid tert-butyl ester | 201225-11-8

• 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: 3-{2-[(2-Chloro-acetyl)-(4-oxo-cyclohexyl)-amino]-ethyl}-indole-1-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 3-[2-[(2-chloroacetyl)-(4-oxocyclohexyl)amino]ethyl]indole-1-carboxylate
• CAS: 201225-11-8
• 化学式: C₂₃H₂₉ClN₂O₄
• 分子量: 432.947
• InChiKey: CJHRSFCNQPHHHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-{2-[(2-Chloro-acetyl)-(4-oxo-cyclohexyl)-amino]-ethyl}-indole-1-carboxylic acid tert-butyl ester 在 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以11%的产率得到2-{2-[1-(tert-butoxycarbonyl)-3-indolyl]ethyl}-2-azabicyclo[3.3.1]nonane-3,6-dione
  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
• 作为产物：
  描述：

  N-[2-(1H-indol-3-yl)ethyl]-1,4-dioxaspiro[4.5]decan-8-amine 在 4-二甲氨基吡啶 、 水 、 magnesium oxide 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 66.0h， 生成 3-{2-[(2-Chloro-acetyl)-(4-oxo-cyclohexyl)-amino]-ethyl}-indole-1-carboxylic acid tert-butyl ester
  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 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.