1-(4-(tert-butyldimethylsilyloxy)phenyl)-2-methyl-1H-indole | 1264995-62-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(4-(tert-butyldimethylsilyloxy)phenyl)-2-methyl-1H-indole
• 英文别名: Tert-butyl-dimethyl-[4-(2-methylindol-1-yl)phenoxy]silane
• CAS: 1264995-62-1
• 化学式: C₂₁H₂₇NOSi
• 分子量: 337.537
• InChiKey: JZWUBHSBASEFMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.32
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  ethyl 2-diazohexanoate 、 1-(4-(tert-butyldimethylsilyloxy)phenyl)-2-methyl-1H-indole 在 tetrakis[μ-(αS)-α-(1,1-dimethylethyl)-2,3-dihydro-1H-naphtho[1,8-cd]pyridine-2-acetato-κO:.kappaO']dirhodium(II)(Rh-Rh) 作用下， 以 甲苯 为溶剂， 生成 ethyl (S)-2-(1-(4-(tert-butyldimethylsilyloxy)phenyl)-2-methyl-1H-indol-3-yl)hexanoate 、 (-)-ethyl (R)-2-(1-(4-(tert-butyldimethylsilyloxy)phenyl)-2-methyl-1H-indol-3-yl)hexanoate
  参考文献：
  名称：

  Rhodium(II)-Catalyzed Enantioselective C−H Functionalization of Indoles

  摘要：

  A catalytic, enantioselective method for the C-H functionalization of indoles by diazo compounds has been achieved. With catalytic amounts of Rh-2(S-NTTL)(4), the putative Rh-carbene intermediates from alpha-alkyl-alpha-diazoesters react with indoles at C(3) to provide alpha-alkyl-alpha-indolylacetates in high yield and enantioselectivity. From DFT calculations, a mechanism is proposed that involves a Rh-ylide intermediate with oxocarbenium character.

  DOI：

  10.1021/ja1093309
• 作为产物：
  描述：

  2-甲基吲哚 、 4-碘叔丁基二甲基硅氧基苯 在 potassium phosphate 、 copper(l) iodide 、 N,N'-二甲基乙二胺 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以68%的产率得到1-(4-(tert-butyldimethylsilyloxy)phenyl)-2-methyl-1H-indole
  参考文献：
  名称：

  Rhodium(II)-Catalyzed Enantioselective C−H Functionalization of Indoles

  摘要：

  A catalytic, enantioselective method for the C-H functionalization of indoles by diazo compounds has been achieved. With catalytic amounts of Rh-2(S-NTTL)(4), the putative Rh-carbene intermediates from alpha-alkyl-alpha-diazoesters react with indoles at C(3) to provide alpha-alkyl-alpha-indolylacetates in high yield and enantioselectivity. From DFT calculations, a mechanism is proposed that involves a Rh-ylide intermediate with oxocarbenium character.

  DOI：

  10.1021/ja1093309

文献信息

• Rhodium(II)-Catalyzed Enantioselective C−H Functionalization of Indoles
  作者：Andrew DeAngelis、Valerie W. Shurtleff、Olga Dmitrenko、Joseph M. Fox

  DOI：10.1021/ja1093309

  日期：2011.2.16

  A catalytic, enantioselective method for the C-H functionalization of indoles by diazo compounds has been achieved. With catalytic amounts of Rh-2(S-NTTL)(4), the putative Rh-carbene intermediates from alpha-alkyl-alpha-diazoesters react with indoles at C(3) to provide alpha-alkyl-alpha-indolylacetates in high yield and enantioselectivity. From DFT calculations, a mechanism is proposed that involves a Rh-ylide intermediate with oxocarbenium character.