N-tert-butoxycarbonyl-7-chloro-2,3-dihydroindole | 143262-18-4

• 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: N-tert-butoxycarbonyl-7-chloro-2,3-dihydroindole
• 英文别名: Xvxcmemyowouqm-uhfffaoysa-；tert-butyl 7-chloro-2,3-dihydroindole-1-carboxylate
• CAS: 143262-18-4
• 化学式: C₁₃H₁₆ClNO₂
• mdl: MFCD13183555
• 分子量: 253.729
• InChiKey: XVXCMEMYOWOUQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二氧化碳 、 N-tert-butoxycarbonyl-7-chloro-2,3-dihydroindole 在 四甲基乙二胺 、 仲丁基锂 作用下， 生成 7-Chloro-2,3-dihydro-indole-1,2-dicarboxylic acid 1-tert-butyl ester
  参考文献：
  名称：

  Asymmetric Deprotonations:  Lithiation of N-(tert-Butoxycarbonyl)indoline with sec-Butyllithium/(−)-Sparteine

  摘要：

  The asymmetric lithiation of N-Boc indoline (1) with s-BuLi/(-)-sparteine and subsequent substitution provides the 2-substituted N-Boc indolines 3 and 5-11 with excellent enantiomeric ratios and in variable yields. The asymmetric lithiation-substitution sequence with N-Boc-7-chloroindoline (12) provides products 13-19 with good enantiomeric ratios. Mechanistic investigation establishes that the enantioselectivities arise from an initial asymmetric deprotonation to provide the enantioenriched and configurationally stable organolithium intermediates (S)-28 and (S)-29, which react stereoselectively with electrophiles.

  DOI：

  10.1021/jo9708856
• 作为产物：
  描述：

  1-Boc-吲哚啉 在 四甲基乙二胺 、 六氯乙烷 、 仲丁基锂 作用下， 生成 N-tert-butoxycarbonyl-7-chloro-2,3-dihydroindole
  参考文献：
  名称：

  Directed Lithiation of 1-(tert-Butoxycarbonyl)indolines. A Convenient Route to 7-Substituted Indolines

  摘要：

  1-(tert-Butoxycarbonyl)indolines were regioselectively lithiated at 7-position with s-BuLi-TMEDA in ether or TBF at -78-degrees-C. The lithiated species were reacted with a range of electrophiles to give 7-substituted indoline derivatives.

  DOI：

  10.3987/com-92-5993

文献信息

• Nucleophilic Addition of α-Metallated Carbamates to Planar Chiral Cationic η³-Allylmolybdenum Complexes: A Stereochemical Study
  作者：Philip Kocienski、John Christopher、Richard Bell、Bernhard Otto

  DOI：10.1055/s-2004-834917

  日期：——

  Chiral α-(O-carbamoyl)alkyl- and α-(N-carbamoyl)alkylcopper(I) reagents derived from (-)-sparteine-mediated asymmetric lithiation of hindered carbamates react with cationic η 3 -allylmolybdenum complexes with retention of configuration.

  衍生自 (-)-sparteine 介导的受阻氨基甲酸酯不对称锂化的手性 α-(O-氨基甲酰基)烷基-和 α-(N-氨基甲酰基)烷基铜 (I) 试剂与阳离子 η 3 -烯丙基钼配合物反应，并保留构型。
• Asymmetric Deprotonations:  Lithiation of <i>N</i>-(<i>tert</i>-Butoxycarbonyl)indoline with <i>sec</i>-Butyllithium/(−)-Sparteine
  作者：Kathleen M. Bertini Gross、Young M. Jun、Peter Beak

  DOI：10.1021/jo9708856

  日期：1997.10.1

  The asymmetric lithiation of N-Boc indoline (1) with s-BuLi/(-)-sparteine and subsequent substitution provides the 2-substituted N-Boc indolines 3 and 5-11 with excellent enantiomeric ratios and in variable yields. The asymmetric lithiation-substitution sequence with N-Boc-7-chloroindoline (12) provides products 13-19 with good enantiomeric ratios. Mechanistic investigation establishes that the enantioselectivities arise from an initial asymmetric deprotonation to provide the enantioenriched and configurationally stable organolithium intermediates (S)-28 and (S)-29, which react stereoselectively with electrophiles.
• Directed Lithiation of 1-(tert-Butoxycarbonyl)indolines. A Convenient Route to 7-Substituted Indolines
  作者：Masatomo Iwao、Tsukasa Kuraishi

  DOI：10.3987/com-92-5993

  日期：——

  1-(tert-Butoxycarbonyl)indolines were regioselectively lithiated at 7-position with s-BuLi-TMEDA in ether or TBF at -78-degrees-C. The lithiated species were reacted with a range of electrophiles to give 7-substituted indoline derivatives.

表征谱图