2-<7-Methyl-5-<(4-methylphenyl)sulfonyl>-6-<(trimethylsilyl)methyl>-6-octenyl>furan

• 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: 2-<7-Methyl-5-<(4-methylphenyl)sulfonyl>-6-<(trimethylsilyl)methyl>-6-octenyl>furan
• 英文别名: [7-(Furan-2-yl)-3-(4-methylphenyl)sulfonyl-2-propan-2-ylideneheptyl]-trimethylsilane
• 化学式: C₂₄H₃₆O₃SSi
• 分子量: 432.7
• InChiKey: AKPIQTWOXSSHEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.82
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-<7-Methyl-5-<(4-methylphenyl)sulfonyl>-6-<(trimethylsilyl)methyl>-6-octenyl>furan 以46%的产率得到
  参考文献：
  名称：

  Harmata Michael, Herron Barry F., J. Org. Chem, 58 (1993) N 26, S 7393-7396

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(4-iodobutyl)furan 、 Trimethyl-[3-methyl-2-[(4-methylphenyl)sulfonylmethyl]but-2-enyl]silane 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以63%的产率得到2-<7-Methyl-5-<(4-methylphenyl)sulfonyl>-6-<(trimethylsilyl)methyl>-6-octenyl>furan
  参考文献：
  名称：

  (Trimethylsilyl)methyl allylic sulfones in intramolecular 4 + 3 cycloadditions

  摘要：

  Treatment of (trimethylsilyl)methyl allylic sulfones tethered to a furan with trimethylaluminum results in the formation of products derived from the intramolecular 4 + 3 cycloaddition of the corresponding allylic cations. 2,5-Disubstitution on the furan precludes the formation of cycloadducts and results in two different classes of products which apparently result from ipso or ortho attack of the allylic cation on the furan ring followed by trapping of the resulting oxonium ions by trimethylaluminum.

  DOI：

  10.1021/jo00078a017

文献信息

• Photochemical activation of trimethylsilylmethyl allylic sulfones for intramolecular 4+3 cycloaddition
  作者：Michael Harmata、Barry F. Herron

  DOI：10.1016/s0040-4039(00)73914-1

  日期：1993.1

  represents the first apparent photochemical generation of acyclic allylic cations for 4+3 cycloadditions. Mechanistically, this process is interpreted as an electron transfer process to form an internal radical cation/radical anion reactive intermediate. This eliminates p-tolylsulfinate anion to form an allylic cation which undergoes an intramolecular 4+3 cycloaddition.

  辐照烯丙基砜4-7会形成4 + 3环加合物8-11。尽管产率很低，但这代表了对于4 + 3环加成反应的无环烯丙基阳离子的第一个明显的光化学生成。从机理上讲，该过程被解释为形成内部自由基阳离子/自由基阴离子反应性中间体的电子转移过程。这消除了对甲苯磺酸亚根阴离子以形成烯丙基阳离子，该烯丙基阳离子经历了分子内4 + 3环加成。
• Harmata Michael, Herron Barry F., J. Org. Chem, 58 (1993) N 26, S 7393-7396
  作者：Harmata Michael, Herron Barry F.

  DOI：——

  日期：——
• (Trimethylsilyl)methyl allylic sulfones in intramolecular 4 + 3 cycloadditions
  作者：Michael Harmata、Barry F. Herron

  DOI：10.1021/jo00078a017

  日期：1993.12

  Treatment of (trimethylsilyl)methyl allylic sulfones tethered to a furan with trimethylaluminum results in the formation of products derived from the intramolecular 4 + 3 cycloaddition of the corresponding allylic cations. 2,5-Disubstitution on the furan precludes the formation of cycloadducts and results in two different classes of products which apparently result from ipso or ortho attack of the allylic cation on the furan ring followed by trapping of the resulting oxonium ions by trimethylaluminum.