(-)-ethyl (R)-5-methyl-2-(1-benzyl-5-fluoro-2-methyl-1H-indol-3-yl)hexanoate | 1264995-16-5

• 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: (-)-ethyl (R)-5-methyl-2-(1-benzyl-5-fluoro-2-methyl-1H-indol-3-yl)hexanoate
• 英文别名: ethyl (2R)-2-(1-benzyl-5-fluoro-2-methylindol-3-yl)-5-methylhexanoate
• CAS: 1264995-16-5
• 化学式: C₂₅H₃₀FNO₂
• 分子量: 395.517
• InChiKey: GWVQTJQNWJOTMA-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-氟-2-甲基吲哚 、 溴甲苯 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) 、 potassium hydroxide 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 1.5h， 生成 (-)-ethyl (R)-5-methyl-2-(1-benzyl-5-fluoro-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

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.