1-(allenylsulfonyl)-2-methyl-3-vinyl-2-cyclohexene | 133846-79-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 磺酰类
• 英文名称: 1-(allenylsulfonyl)-2-methyl-3-vinyl-2-cyclohexene
• CAS: 133846-79-4
• 化学式: C₁₂H₁₆O₂S
• 分子量: 224.324
• InChiKey: BJBJIGOMXNTEAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(allenylsulfonyl)-2-methyl-3-vinyl-2-cyclohexene 以 甲苯 为溶剂， 反应 5.0h， 以44%的产率得到10-methyl-6-vinyl-2-thiatricyclo<4.3.1.0^4,10>dec-3-ene 2,2-dioxide
  参考文献：
  名称：

  磺酰基烯丙烯的竞争性分子内[4 + 2]环加成和[2 + 2]环加成

  摘要：

  磺酰亚丙基的热反应通过分子内Diels-Alder（[4 + 2]）反应和/或[2 + 2]环加成反应进行，具体取决于取代方式，其作用是取决于C的反应路径的切换（2）位置。

  DOI：

  10.1016/s0040-4039(00)79665-1
• 作为产物：
  描述：

  2-Methyl-3-vinyl-cyclohex-2-enethiol 在 aluminum oxide 、 sodium hydroxide 、 四丁基硫酸氢铵 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 3.83h， 生成 1-(allenylsulfonyl)-2-methyl-3-vinyl-2-cyclohexene
  参考文献：
  名称：

  Periselective intramolecular cycloaddition of allenyl thioethers and allenyl sulfones

  摘要：

  The thermal intramolecular cycloaddition reactions of variously substituted allenyl 3-vinyl-2-cyclohexenyl thioethers and sulfones and the base-catalyzed intramolecular cycloaddition reactions of several propargyl 3-vinyl-2-cyclohexenyl thioethers have been investigated. When there was no steric congestion in the transition state, the substrates gave Diels-Alder ([4 + 2]) adducts, When a substituent was introduced at C(2) of the cyclohexene in such way as to disfavor the s-cis conformation of the butadiene moiety in the transition state, novel [2 + 2] cycloadducts 4, 37, and 40 were obtained from allenyl sulfones, 1b, 25, and 27, and allenyl thioether 20b underwent a tandem [2 + 2] cycloaddition/[3,3]-sigmatropic rearrangement reaction sequence to produce 30 as the major product. C(4)-substituted compounds 22a,b and 28 underwent Diels-Alder ([4 + 2]) reactions exclusively; C(G)-substituted allenyl thioethers 24a,b and 26 did not afford the cycloadducts. The structure of [2 + 2] adduct 4 was confirmed by single-crystal X-ray analysis to be a strained tricyclic containing 4-, 5-, and 6-membered rings.

  DOI：

  10.1021/jo00086a010