methyl 2-(9-(2-(tert-butyldimethylsilyloxy)ethyl)-6-oxo-9-vinyl-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetate | 1605288-01-4

• 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: methyl 2-(9-(2-(tert-butyldimethylsilyloxy)ethyl)-6-oxo-9-vinyl-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetate
• 英文别名: Methyl 2-[9-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-9-ethenyl-6-oxo-7,8-dihydropyrido[1,2-a]indol-10-yl]acetate；methyl 2-[9-[2-[tert-butyl(dimethyl)silyl]oxyethyl]-9-ethenyl-6-oxo-7,8-dihydropyrido[1,2-a]indol-10-yl]acetate
• CAS: 1605288-01-4
• 化学式: C₂₅H₃₅NO₄Si
• 分子量: 441.643
• InChiKey: ZWJFXFRACFPFDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.63
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-(9-(2-(tert-butyldimethylsilyloxy)ethyl)-6-oxo-9-vinyl-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetate 在 盐酸 、 三甲基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 methyl 2-(9-(2-((2-nitrophenyl)selanyl)ethyl)-6-oxo-9-vinyl-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetate
  参考文献：
  名称：

  Total Syntheses of Leuconoxine, Leuconodine B, and Melodinine E by Oxidative Cyclic Aminal Formation and Diastereoselective Ring-Closing Metathesis

  摘要：

  Total syntheses of leuconodine B, melodinine E, and leuconoxine were accomplished via a divergent route. The [5.5.6.6]diazafenestrane skeleton was constructed from an indole-3-acetamide derivative via DMDO oxidation to hydroxylindolenine, TMSOTf/2,6-lutidine mediated cyclic aminal formation, and diastereoseletive ring-closing metathesis of a triene derivative.

  DOI：

  10.1021/ol500903e
• 作为产物：
  描述：

  1,4-环己二酮 在 吡啶 、 1,2,2,6,6-五甲基哌啶 、 咪唑 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 正丁基锂 、 lithium hydroxide monohydrate 、 二碳酸二叔丁酯 、 potassium carbonate 、 间氯过氧苯甲酸 、 三(邻甲基苯基)磷 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 51.33h， 生成 methyl 2-(9-(2-(tert-butyldimethylsilyloxy)ethyl)-6-oxo-9-vinyl-6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl)acetate
  参考文献：
  名称：

  Total Syntheses of Leuconoxine, Leuconodine B, and Melodinine E by Oxidative Cyclic Aminal Formation and Diastereoselective Ring-Closing Metathesis

  摘要：

  Total syntheses of leuconodine B, melodinine E, and leuconoxine were accomplished via a divergent route. The [5.5.6.6]diazafenestrane skeleton was constructed from an indole-3-acetamide derivative via DMDO oxidation to hydroxylindolenine, TMSOTf/2,6-lutidine mediated cyclic aminal formation, and diastereoseletive ring-closing metathesis of a triene derivative.

  DOI：

  10.1021/ol500903e

文献信息

• Total Syntheses of Leuconoxine, Leuconodine B, and Melodinine E by Oxidative Cyclic Aminal Formation and Diastereoselective Ring-Closing Metathesis
  作者：Atsushi Umehara、Hirofumi Ueda、Hidetoshi Tokuyama

  DOI：10.1021/ol500903e

  日期：2014.5.2

  Total syntheses of leuconodine B, melodinine E, and leuconoxine were accomplished via a divergent route. The [5.5.6.6]diazafenestrane skeleton was constructed from an indole-3-acetamide derivative via DMDO oxidation to hydroxylindolenine, TMSOTf/2,6-lutidine mediated cyclic aminal formation, and diastereoseletive ring-closing metathesis of a triene derivative.