3-methyl-N-(tetrahydrofuran-2-yl)-1H-indole | 651712-33-3

• 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: 3-methyl-N-(tetrahydrofuran-2-yl)-1H-indole
• 英文别名: 3-Methyl-1-(oxolan-2-yl)-1H-indole；3-methyl-1-(oxolan-2-yl)indole
• CAS: 651712-33-3
• 化学式: C₁₃H₁₅NO
• 分子量: 201.268
• InChiKey: FMWJXERRSMUNBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  14.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  thiobutyrolactone 、 3-methylindolylmagnesium bromide 在 trimethoxonium tetrafluoroborate 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 反应 1.41h， 以50%的产率得到3-methyl-N-(tetrahydrofuran-2-yl)-1H-indole
  参考文献：
  名称：

  Synthesis of N‐Glycoside Analogs via Thionolactones

  摘要：

  Indolyl N-glycoside analogs were obtained by a two-step sequence via indole N-thioamides. Treatment of thionobutyrolactone with indolylmagnesium bromide provides the corresponding indole N-thioamide. The use of 10:1 toluene:THF as solvent is important in favoring N- over C3-acylation. Treatment of the omega-hydroxythioamide with 2 equiv of Meerwein's reagent followed by sodium borohydride gives the corresponding N-(tetrahydrofuranyl)indole. Addition of carbon nucleophiles gives access to ketose nucleoside analogs, while activation of the omega-hydroxyl group can give access to tetrahydrothiophene N-glycosides.

  DOI：

  10.1081/car-120026472

文献信息

• Synthesis of <i>N</i>‐Glycoside Analogs via Thionolactones
  作者：Wendong Wang、Pornpun Rattananakin、Peter G. Goekjian

  DOI：10.1081/car-120026472

  日期：2003.12.31

  Indolyl N-glycoside analogs were obtained by a two-step sequence via indole N-thioamides. Treatment of thionobutyrolactone with indolylmagnesium bromide provides the corresponding indole N-thioamide. The use of 10:1 toluene:THF as solvent is important in favoring N- over C3-acylation. Treatment of the omega-hydroxythioamide with 2 equiv of Meerwein's reagent followed by sodium borohydride gives the corresponding N-(tetrahydrofuranyl)indole. Addition of carbon nucleophiles gives access to ketose nucleoside analogs, while activation of the omega-hydroxyl group can give access to tetrahydrothiophene N-glycosides.