3-(2-phenylsulfonyl-2-propenyl)-1-methylindole | 922139-25-1

• 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-(2-phenylsulfonyl-2-propenyl)-1-methylindole
• 英文别名: 3-[2-(Benzenesulfonyl)prop-2-en-1-yl]-1-methyl-1H-indole；3-[2-(benzenesulfonyl)prop-2-enyl]-1-methylindole
• CAS: 922139-25-1
• 化学式: C₁₈H₁₇NO₂S
• 分子量: 311.404
• InChiKey: NAMCKSCLSVABGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-phenylsulfonyl-2-propenyl acetate 、 1-甲基吲哚 在 bis(acetylacetonato)palladium(II) 、 三苯基膦 作用下， 以 溶剂黄146 为溶剂， 反应 11.0h， 以76%的产率得到3-(2-phenylsulfonyl-2-propenyl)-1-methylindole
  参考文献：
  名称：

  Palladium-Catalyzed Functionalization of Indoles with 2-Acetoxymethyl-Substituted Electron-Deficient Alkenes

  摘要：

  New functionalizations of indoles via palladium-catalyzed reaction of indoles and 2-acetoxymethyl-substituted electron-deficient alkenes are reported. It was found that for N-protected indoles the reaction proceeded smoothly in the presence of 5 mol % of Pd(acac)(2) and 10 mol % of PPh3 at 80 degrees C in HOAc, while for N-unprotected indoles, the reaction was carried out by using 5 mol % of Pd(dba)(2) or 2.5 mol % of Pd-2(dba)(3), CHCl3 with 10 mol % of 2,2'-bipyridine as the catalyst in toluene. This strategy allows the selective installation of electron-deficient olefin functionality at the 3-position of indoles, which might be difficult to obtain by other methods and can be further elaborated.

  DOI：

  10.1021/jo061546s

文献信息

• Palladium-Catalyzed Functionalization of Indoles with 2-Acetoxymethyl-Substituted Electron-Deficient Alkenes
  作者：Shengming Ma、Shichao Yu、Zhihua Peng、Hao Guo

  DOI：10.1021/jo061546s

  日期：2006.12.1

  New functionalizations of indoles via palladium-catalyzed reaction of indoles and 2-acetoxymethyl-substituted electron-deficient alkenes are reported. It was found that for N-protected indoles the reaction proceeded smoothly in the presence of 5 mol % of Pd(acac)(2) and 10 mol % of PPh3 at 80 degrees C in HOAc, while for N-unprotected indoles, the reaction was carried out by using 5 mol % of Pd(dba)(2) or 2.5 mol % of Pd-2(dba)(3), CHCl3 with 10 mol % of 2,2'-bipyridine as the catalyst in toluene. This strategy allows the selective installation of electron-deficient olefin functionality at the 3-position of indoles, which might be difficult to obtain by other methods and can be further elaborated.