1-triisopropylsilyl-2-methylindoline | 352561-34-3

• 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: 1-triisopropylsilyl-2-methylindoline
• 英文别名: 1triisopropyl-2-methylindoline；(2-Methyl-2,3-dihydroindol-1-yl)-tri(propan-2-yl)silane
• CAS: 352561-34-3
• 化学式: C₁₈H₃₁NSi
• 分子量: 289.536
• InChiKey: OGYFRUPQEVDFJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  六羰基铬 、 1-triisopropylsilyl-2-methylindoline 以 二丁醚 为溶剂， 以69%的产率得到endo-(η(6)-1-triisopropylsilyl-2-methylindoline)tricarbonylchromium(0)
  参考文献：
  名称：

  Regio- and diastereoselective formation of some (η6-2-methylindoline)tricarbonylchromium(0) complex derivatives

  摘要：

  Complexation of 2-methylindoline 1 and its derivatives 2 and 3 with Cr(CO)(6) gave complexes 4-9. With the TIPS group attached to the nitrogen atom as in compound 3, the complexation was completely diastereoselective producing the endo complex 9. Treatment of the metallated complexes 8 and 9 with 2-halobenzoyl chlorides as electrophiles allowed for totally regioselective functionalisation at C(4), while the exo complex 6 was functionalised both at C(4) and C(7); with TMSCl and TIPSCl as electrophiles, the endo complex 9 also exhibited minor exo benzylic substitution to give 25 and 27. Oxidative decomplexation of the indoline complexes efficiently releases the free 4-substituted indolines. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)00694-5
• 作为产物：
  描述：

  三异丙基氯硅烷 、 2-甲基吲哚啉 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 27.0h， 以67%的产率得到1-triisopropylsilyl-2-methylindoline
  参考文献：
  名称：

  Regio- and diastereoselective formation of some (η6-2-methylindoline)tricarbonylchromium(0) complex derivatives

  摘要：

  Complexation of 2-methylindoline 1 and its derivatives 2 and 3 with Cr(CO)(6) gave complexes 4-9. With the TIPS group attached to the nitrogen atom as in compound 3, the complexation was completely diastereoselective producing the endo complex 9. Treatment of the metallated complexes 8 and 9 with 2-halobenzoyl chlorides as electrophiles allowed for totally regioselective functionalisation at C(4), while the exo complex 6 was functionalised both at C(4) and C(7); with TMSCl and TIPSCl as electrophiles, the endo complex 9 also exhibited minor exo benzylic substitution to give 25 and 27. Oxidative decomplexation of the indoline complexes efficiently releases the free 4-substituted indolines. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)00694-5

文献信息

• Regio- and diastereoselective formation of some (η6-2-methylindoline)tricarbonylchromium(0) complex derivatives
  作者：M.Filomena D Costa、M.Rute G da Costa、M.J Marcelo Curto

  DOI：10.1016/s0022-328x(01)00694-5

  日期：2001.4

  Complexation of 2-methylindoline 1 and its derivatives 2 and 3 with Cr(CO)(6) gave complexes 4-9. With the TIPS group attached to the nitrogen atom as in compound 3, the complexation was completely diastereoselective producing the endo complex 9. Treatment of the metallated complexes 8 and 9 with 2-halobenzoyl chlorides as electrophiles allowed for totally regioselective functionalisation at C(4), while the exo complex 6 was functionalised both at C(4) and C(7); with TMSCl and TIPSCl as electrophiles, the endo complex 9 also exhibited minor exo benzylic substitution to give 25 and 27. Oxidative decomplexation of the indoline complexes efficiently releases the free 4-substituted indolines. (C) 2001 Elsevier Science B.V. All rights reserved.