3,5,5-tris(phenylsulfonyl)-8-methylnona-1,2,7-triene | 149167-15-7

• 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: 3,5,5-tris(phenylsulfonyl)-8-methylnona-1,2,7-triene
• CAS: 149167-15-7
• 化学式: C₂₈H₂₈O₆S₃
• 分子量: 556.725
• InChiKey: CWPDBPYKWLFPGY-UHFFFAOYSA-N

物化性质

• 沸点：
  814.4±65.0 °C(predicted)
• 密度：
  1.267±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,5,5-tris(phenylsulfonyl)-8-methylnona-1,2,7-triene 以 苯 为溶剂， 反应 0.75h， 以90%的产率得到7,7-dimethyl-2,4,4-tris(phenylsulfonyl)bicyclo<4.2.0>oct-1-ene
  参考文献：
  名称：

  (Phenylsulfonyl)allenes as Substrates for Cycloaddition Reactions: Intramolecular Cyclizations onto Unactivated Alkenes

  摘要：

  The reaction of a series of allyl-substituted bis(phenylsulfonyl)methanes or dimethyl malonates with 2,3-bis(phenylsulfonyl)-1,3-butadiene in the presence of base afforded alkenyl-substituted allenes in good yield. The reaction proceeds by initial attack of the soft carbanion onto the terminal position of the diene, and this is followed by PhSO(2)(-) elimination to give the phenylsulfonyl-substituted allene. Themal [2 + 2]-cycloaddition proceeded across the C-1-C-2 double bond of the allene with completely sterospecificity. Stepwise bonding prefers to occur in a 1,6-exo manner rather than in a 1,7-endo fashion. Substitution at the 7-position of the pi-bond causes a crossover in the regioselectivity of the [2 + 2]-cycloaddition process. All products can be rationalized by a mechanism which includes an initial carbon-carbon bond formation involving the central allene carbon to give a diradical intermediate. The product distribution is then determined by the substitution pattern of the alkene and the fate of the diradical intermediate.

  DOI：

  10.1021/ja00132a005
• 作为产物：
  描述：

  双苯磺酸甲烷 在 sodium hydride 作用下， 反应 13.25h， 生成 3,5,5-tris(phenylsulfonyl)-8-methylnona-1,2,7-triene
  参考文献：
  名称：

  (Phenylsulfonyl)allenes as Substrates for Cycloaddition Reactions: Intramolecular Cyclizations onto Unactivated Alkenes

  摘要：

  The reaction of a series of allyl-substituted bis(phenylsulfonyl)methanes or dimethyl malonates with 2,3-bis(phenylsulfonyl)-1,3-butadiene in the presence of base afforded alkenyl-substituted allenes in good yield. The reaction proceeds by initial attack of the soft carbanion onto the terminal position of the diene, and this is followed by PhSO(2)(-) elimination to give the phenylsulfonyl-substituted allene. Themal [2 + 2]-cycloaddition proceeded across the C-1-C-2 double bond of the allene with completely sterospecificity. Stepwise bonding prefers to occur in a 1,6-exo manner rather than in a 1,7-endo fashion. Substitution at the 7-position of the pi-bond causes a crossover in the regioselectivity of the [2 + 2]-cycloaddition process. All products can be rationalized by a mechanism which includes an initial carbon-carbon bond formation involving the central allene carbon to give a diradical intermediate. The product distribution is then determined by the substitution pattern of the alkene and the fate of the diradical intermediate.

  DOI：

  10.1021/ja00132a005

文献信息

• Peri and stereoselectivity effects in the intramolecular [2+2]-cycloaddition reaction of phenylsulfonyl-substituted allenes
  作者：Albert Padwa、Michelle A. Filipkowski、Michael Meske、Scott H. Watterson、Zhijie Ni

  DOI：10.1021/ja00062a054

  日期：1993.5
• (Phenylsulfonyl)allenes as Substrates for Cycloaddition Reactions: Intramolecular Cyclizations onto Unactivated Alkenes
  作者：Albert Padwa、Michael Meske、S. Shaun Murphree、Scott H. Watterson、Zhijie Ni

  DOI：10.1021/ja00132a005

  日期：1995.7

  The reaction of a series of allyl-substituted bis(phenylsulfonyl)methanes or dimethyl malonates with 2,3-bis(phenylsulfonyl)-1,3-butadiene in the presence of base afforded alkenyl-substituted allenes in good yield. The reaction proceeds by initial attack of the soft carbanion onto the terminal position of the diene, and this is followed by PhSO(2)(-) elimination to give the phenylsulfonyl-substituted allene. Themal [2 + 2]-cycloaddition proceeded across the C-1-C-2 double bond of the allene with completely sterospecificity. Stepwise bonding prefers to occur in a 1,6-exo manner rather than in a 1,7-endo fashion. Substitution at the 7-position of the pi-bond causes a crossover in the regioselectivity of the [2 + 2]-cycloaddition process. All products can be rationalized by a mechanism which includes an initial carbon-carbon bond formation involving the central allene carbon to give a diradical intermediate. The product distribution is then determined by the substitution pattern of the alkene and the fate of the diradical intermediate.