5-bromo-1-trimethylsilanyl-2,3-dihydro-1H-indole | 912561-28-5

• 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: 5-bromo-1-trimethylsilanyl-2,3-dihydro-1H-indole
• 英文别名: (5-Bromo-2,3-dihydroindol-1-yl)-trimethylsilane
• CAS: 912561-28-5
• 化学式: C₁₁H₁₆BrNSi
• 分子量: 270.244
• InChiKey: NHXFJTZMKTUYAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  5-bromo-1-trimethylsilanyl-2,3-dihydro-1H-indole 、 5-O-三苯甲基-2,3-O-异亚丙基-D-呋喃核糖 在 2-氟-1-甲基吡啶翁对甲苯磺酸盐 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以92%的产率得到1-(5-O-triphenylmethyl-2,3-O-isopropylidene-α-D-ribofuranosyl)-5-bromoindoline
  参考文献：
  名称：

  Regioselective Glycosylation: Synthesis of α-Indoline Nucleosides

  摘要：

  Novel indoline ribonucleosides with the alpha-N-glycoside configuration are synthesized with very high regioselectivily in 90-96% yield, using TMS protected indolines and 2,3-O-(1-methylethylidene)-5-O-(triphenylmethyl)-alpha/beta-D-ribofuranose. The structures of these ribonucleosides were elucidated with X-ray crystallography as well as 2D (NOESY COSY and HMQC) NMR spectroscopy.

  DOI：

  10.1081/ncn-200067398
• 作为产物：
  描述：

  5-溴吲哚 在 正丁基锂 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 反应 12.0h， 生成 5-bromo-1-trimethylsilanyl-2,3-dihydro-1H-indole
  参考文献：
  名称：

  Regioselective Glycosylation: Synthesis of α-Indoline Nucleosides

  摘要：

  Novel indoline ribonucleosides with the alpha-N-glycoside configuration are synthesized with very high regioselectivily in 90-96% yield, using TMS protected indolines and 2,3-O-(1-methylethylidene)-5-O-(triphenylmethyl)-alpha/beta-D-ribofuranose. The structures of these ribonucleosides were elucidated with X-ray crystallography as well as 2D (NOESY COSY and HMQC) NMR spectroscopy.

  DOI：

  10.1081/ncn-200067398

文献信息

• Regioselective Glycosylation: Synthesis of <i>α</i>-Indoline Nucleosides
  作者：Kenneth L. Brown、Tilak Chandra、Shawn Zou、Edward J. Valente

  DOI：10.1081/ncn-200067398

  日期：2005.7.1

  Novel indoline ribonucleosides with the alpha-N-glycoside configuration are synthesized with very high regioselectivily in 90-96% yield, using TMS protected indolines and 2,3-O-(1-methylethylidene)-5-O-(triphenylmethyl)-alpha/beta-D-ribofuranose. The structures of these ribonucleosides were elucidated with X-ray crystallography as well as 2D (NOESY COSY and HMQC) NMR spectroscopy.