1,3-bis(phenylsulfonyl)-4-phenyl-1,3-butadiene | 96540-11-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,3-bis(phenylsulfonyl)-4-phenyl-1,3-butadiene
• 英文别名: [(1Z,3E)-2,4-bis(benzenesulfonyl)buta-1,3-dienyl]benzene
• CAS: 96540-11-3；133167-27-8
• 化学式: C₂₂H₁₈O₄S₂
• 分子量: 410.515
• InChiKey: ORYDCMXESDNDEZ-PYILIBOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-二甲基硫代甲酰胺 、 1,3-bis(phenylsulfonyl)-4-phenyl-1,3-butadiene 以 苯 为溶剂， 反应 96.0h， 以84%的产率得到3,5-bis(phenylsulfonyl)-2-phenyl-2H-thiopyran
  参考文献：
  名称：

  Cycloaddition chemistry of 1,3- and 2,3-bis(phenylsulfonyl)-1,3-dienes with enamines and ynamines

  摘要：

  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.

  DOI：

  10.1021/jo00039a008
• 作为产物：
  描述：

  (E)-1,3-双(苯基磺酰基)丙烯 、 苯甲醛 、 溶剂黄146 、 哌啶 、 正戊烷 以83%的产率得到
  参考文献：
  名称：

  MASUYAMA, YOSHIRO;SATO, HIROKO;KURUSU, YASUHIKO, TETRAHEDRON LETT., 1985, 26, N 1, 67-68

  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.
• MASUYAMA, YOSHIRO;SATO, HIROKO;KURUSU, YASUHIKO, TETRAHEDRON LETT., 1985, 26, N 1, 67-68
  作者：MASUYAMA, YOSHIRO、SATO, HIROKO、KURUSU, YASUHIKO

  DOI：——

  日期：——