methyl 9-methyl-4-(p-tolyl)-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole-3-carboxylate

• 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: methyl 9-methyl-4-(p-tolyl)-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole-3-carboxylate
• 英文别名: methyl (3S,4S)-9-methyl-4-(4-methylphenyl)-3,4-dihydro-2H-thiopyrano[2,3-b]indole-3-carboxylate
• 化学式: C₂₁H₂₁NO₂S
• 分子量: 351.469
• InChiKey: DPOJHKQINNAJDL-FUHWJXTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-甲基-1,3-二氢吲哚-2-硫酮 、 methyl 2-(acetoxy(4-methylphenyl)methyl)acrylate 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以87%的产率得到methyl 9-methyl-4-(p-tolyl)-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole-3-carboxylate
  参考文献：
  名称：

  The stereoselective synthesis of tetrahydrothiopyrano[2,3-b]indole skeletons via tandem reaction of indoline-2-thiones to Baylis–Hillman adduct acetates

  摘要：

  Indoline-2-thiones (5) were applied as 1,3-dinucleophiles in a tandem reaction with Baylis-Hillman adduct acetates (4) to give novel tetrahydrothiopyrano[2,3-b]indole skeletons (6). The effect of different solvents, bases, and catalysts on the yields and stereochemical outcome was studied in detail. The results indicated that acetonitrile as solvent and K2CO3 as base, under reflux conditions, were the optimum conditions. Products 6a-6l were obtained in high diastereoselectivity and yield (up to 94%). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.043