3-(2-(phenylsulfonyl)-2,3-butadienyl)indole | 141362-27-8

• 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)-2,3-butadienyl)indole
• CAS: 141362-27-8
• 化学式: C₁₈H₁₅NO₂S
• 分子量: 309.389
• InChiKey: QFSPQAICUXDATM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  58.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吲哚 、 2,3-bis(phenylsulfonyl)-1,3-butadiene 在 甲基溴化镁 作用下， 生成 3-(2-(phenylsulfonyl)-2,3-butadienyl)indole
  参考文献：
  名称：

  Barnwell, Neil; Beddoes, Roy L.; Mitchell, Michael B., Heterocycles, 1994, vol. 37, # l, p. 175 - 180

  摘要：

  DOI：

文献信息

• Cycloaddition chemistry of 1,3- and 2,3-bis(phenylsulfonyl)-1,3-dienes with enamines and ynamines
  作者：Albert Padwa、Yves Gareau、Brian Harrison、Augusto Rodriguez

  DOI：10.1021/jo00039a008

  日期：1992.6

  1,3- and 2,3-bis(phenylsulfonyl) dienes were found to react smoothly with a variety of enamimes and enamine equivalents to give [4 + 2]-cycloadducts in excellent yields. The cycloaddition proceeds with high regioselectivity affording carbocycles as well as heterocycles. The reactivity of the 1,3-isomer was found to be much greater than the 2,3-isomer and is a consequence of both conformational and electronic factors. Formation of rearranged cycloadducts occurs when unactivated enamines are used with the 2,3-substituted diene. This reaction occurs by an initial rearrangement of the 2,3-diene to the 1,3-isomer followed by cycloaddition with the enamine. Cycloaddition of several 4-substituted 1,3-bis(phenylsulfonyl)butadienes with amidines and thioformamide gave dihydropyridines and thiopyrans, respectively. Indole reacts with both the 1,3- and 2,3-dienes to give the same product distribution of epimeric carbazoles. An entirely different reaction occurred when 1-indolylmagnesium iodide was used. The 2,3-diene reacts with 1-(diethylamino)-1-propyne at low temperatures to give a [2 + 2]-cyloadduct. Reaction of the isomeric 1,3-diene with the same ynamine gave [4 + 2]-cycloadducts as did several 4-substituted 1,3-bis(phenylsulfonyl)butadienes.