5,5-dimethy-3-vinyl-2-cyclohexenyl thioacetate | 155996-11-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代羧酸及其衍生物
• 英文名称: 5,5-dimethy-3-vinyl-2-cyclohexenyl thioacetate
• 英文别名: S-(3-ethenyl-5,5-dimethylcyclohex-2-en-1-yl) ethanethioate
• CAS: 155996-11-5
• 化学式: C₁₂H₁₈OS
• 分子量: 210.34
• InChiKey: RFAVRFXSFZBODY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,5-dimethy-3-vinyl-2-cyclohexenyl thioacetate 在 氢氧化钾 、 sodium hydroxide 、 四丁基硫酸氢铵 作用下， 以 乙醇 、 苯 为溶剂， 反应 0.67h， 生成 5,5-dimethyl-1-(2-propynylthio)-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
• 作为产物：
  描述：

  3-乙烯基-5,5-二甲基环己-2-烯-1-醇 以78%的产率得到
  参考文献：
  名称：

  Yeo Sin-Koo, Shiro Motoo, Kanematsu Ken, J. Org. Chem, 59 (1994) N 7, S 1621-1632

  摘要：

  DOI：

文献信息

• Yeo Sin-Koo, Shiro Motoo, Kanematsu Ken, J. Org. Chem, 59 (1994) N 7, S 1621-1632
  作者：Yeo Sin-Koo, Shiro Motoo, Kanematsu Ken

  DOI：——

  日期：——
• Periselective intramolecular cycloaddition of allenyl thioethers and allenyl sulfones
  作者：Sin-Koo Yeo、Motoo Shiro、Ken Kanematsu

  DOI：10.1021/jo00086a010

  日期：1994.4

  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.