tert-butyl 6-isopropyl-1H-indole-1-carboxylate

• 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: tert-butyl 6-isopropyl-1H-indole-1-carboxylate
• 英文别名: Tert-butyl 6-propan-2-ylindole-1-carboxylate；tert-butyl 6-propan-2-ylindole-1-carboxylate
• 化学式: C₁₆H₂₁NO₂
• 分子量: 259.348
• InChiKey: BNLGMIAUMIORNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-BOC-6-氯吲哚 、 异丙基硼酸 在 methanesulfonato tri(tert-butyl)phosphine (2'-amino-1,1‘-biphenyl-2-yl) palladium (II) 、 potassium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 24.0h， 以87%的产率得到tert-butyl 6-isopropyl-1H-indole-1-carboxylate
  参考文献：
  名称：

  Stereospecific Pd-Catalyzed Cross-Coupling Reactions of Secondary Alkylboron Nucleophiles and Aryl Chlorides

  摘要：

  We report the development of a Pd-catalyzed process for the stereospecific cross-coupling of unactivated secondary alkylboron nucleophiles and aryl chlorides. This process tolerates the use of secondary alkylboronic acids and secondary alkyltrifluoroborates and occurs without significant isomerization of the alkyl nucelophile. Optically active secondary alkyltrifluoroborate reagents undergo cross-coupling reactions with stereospecific inversion of configuration using this method.

  DOI：

  10.1021/ja508815w

文献信息

• Stereospecific Pd-Catalyzed Cross-Coupling Reactions of Secondary Alkylboron Nucleophiles and Aryl Chlorides
  作者：Ling Li、Shibin Zhao、Amruta Joshi-Pangu、Mohamed Diane、Mark R. Biscoe

  DOI：10.1021/ja508815w

  日期：2014.10.8

  We report the development of a Pd-catalyzed process for the stereospecific cross-coupling of unactivated secondary alkylboron nucleophiles and aryl chlorides. This process tolerates the use of secondary alkylboronic acids and secondary alkyltrifluoroborates and occurs without significant isomerization of the alkyl nucelophile. Optically active secondary alkyltrifluoroborate reagents undergo cross-coupling reactions with stereospecific inversion of configuration using this method.