3-methylindolylmagnesium bromide | 62454-37-9

• 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-methylindolylmagnesium bromide
• 英文别名: (3-methylindol-1-yl)magnesium bromide；Magnesium bromide 3-methylindol-1-ide (1/1/1)；magnesium;3-methylindol-1-ide;bromide
• CAS: 62454-37-9
• 化学式: Br*C₉H₈N*Mg
• 分子量: 234.378
• InChiKey: SMKVPTMXYUXWCM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.27
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-内酯 、 3-methylindolylmagnesium bromide 以 四氢呋喃 、 甲苯 为溶剂， 以100%的产率得到(2R,3S,4R,5R)-2,3,4,6-Tetrakis-benzyloxy-5-hydroxy-1-(3-methyl-indol-1-yl)-hexan-1-one
  参考文献：
  名称：

  An amide orthoesterification route to N-(1′-alkylthioglucopyranosyl)indoles

  摘要：

  The addition of 3-methylindolylmagnesium bromide to tetra-O-benzyl-alpha-D-gluconothionolactone yields the expected indole N-gluconothioamide as its hemiorthothioamide tautomer. The thiol function is alkylated to yield the corresponding orthothioamide, a l'-alkylthio-substituted N-glycoside. Alternatively, the l'-alkylthio-N-glycoside can be accessed from the corresponding indole N-gluconamide via a boron trifluoride-etherate mediated orthoesterification with ethanethiol. Radical reduction of the orthothioamide yields the N-glycosides in 2:1 stereoselectivity in favor of the beta-N-glycoside, while reduction via the oxonium ion leads to an improved 6:1 selectivity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.135

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.