3-methylthio-4-trimethylsilyl-1,2-butadiene | 153338-87-5

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: 3-methylthio-4-trimethylsilyl-1,2-butadiene
• 英文别名: 1-methylthio-1-trimethylsilylmethylallene
• CAS: 153338-87-5
• 化学式: C₈H₁₆SSi
• 分子量: 172.367
• InChiKey: TVQPBVBOLGSAOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methylthio-4-trimethylsilyl-1,2-butadiene 在 二氯乙基铝 disodium hydrogenphosphate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 3.0h， 生成 2-Methanesulfonyl-3-methylene-2-trimethylsilanylmethyl-cyclobutanecarbonitrile
  参考文献：
  名称：

  New access to Di-exo-methylenecyclobutanes via [2 + 2] cycloaddition of 3-methylthio-4-trimethylsilyl-1,2-butadiene with alkenes mediated by a Lewis acid

  摘要：

  Methylthio-substituted allenylmethylsilane, a kind of allylsilane, undergoes only [2 + 2] cycloaddition reaction with alkenes mediated by a Lewis acid to afford the corresponding methylenecyclobutanes which are readily converted to di-exo-methylenecyclobutanes by rite sequential oxidation-1,2-elimination in good yield. Di-exo-methylenecyclobutane is also successfully applied to construct a bicyclo[5.2.0]nonenone skeleton by the reaction with 2-oxyallyl cation.

  DOI：

  10.1016/s0040-4039(00)61469-7
• 作为产物：
  描述：

  碘甲基三甲基硅烷 、 1-甲硫基-1-丙炔 在 lithium diisopropyl amide 作用下， 以96%的产率得到3-methylthio-4-trimethylsilyl-1,2-butadiene
  参考文献：
  名称：

  New access to Di-exo-methylenecyclobutanes via [2 + 2] cycloaddition of 3-methylthio-4-trimethylsilyl-1,2-butadiene with alkenes mediated by a Lewis acid

  摘要：

  Methylthio-substituted allenylmethylsilane, a kind of allylsilane, undergoes only [2 + 2] cycloaddition reaction with alkenes mediated by a Lewis acid to afford the corresponding methylenecyclobutanes which are readily converted to di-exo-methylenecyclobutanes by rite sequential oxidation-1,2-elimination in good yield. Di-exo-methylenecyclobutane is also successfully applied to construct a bicyclo[5.2.0]nonenone skeleton by the reaction with 2-oxyallyl cation.

  DOI：

  10.1016/s0040-4039(00)61469-7

文献信息

• Ene preference in the reaction of allenylmethylsilanes with hetero-double bonds mediated by a Lewis acid
  作者：Makoto Hojo、Chikara Murakami、Hidenori Aihara、Kyoji Tomita、Katsukiyo Miura、Akira Hosomi

  DOI：10.1016/0022-328x(95)00306-b

  日期：1995.9

  Methylthio- and methoxy-substituted allenylmethylsilanes, a kind of allylsilanes, undergo the ene-type reaction, not the usual allylsilane-type reaction accompanying by desilylation, with carbonyl and azo compounds mediated by a Lewis acid. The corresponding 1-silyl-substituted functionalized 1,3-dienes are obtained in good yields.

  甲硫基和甲氧基取代的烯丙基甲基硅烷是一种烯丙基硅烷，它与路易斯酸介导的羰基和偶氮化合物进行烯类反应，而不是伴随甲硅烷基化反应的通常的烯丙基硅烷类反应。以良好的产率获得相应的1-甲硅烷基取代的官能化的1，3-二烯。