[1,3]Dithian-2-yl-(4-methoxy-phenyl)-dimethyl-silane | 202349-09-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [1,3]Dithian-2-yl-(4-methoxy-phenyl)-dimethyl-silane
• 英文别名: 1,3-dithian-2-yl-(4-methoxyphenyl)-dimethylsilane
• CAS: 202349-09-5
• 化学式: C₁₃H₂₀OS₂Si
• 分子量: 284.519
• InChiKey: XUDDWIJWPSFAMD-UHFFFAOYSA-N

物化性质

• 沸点：
  387.5±42.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [1,3]Dithian-2-yl-(4-methoxy-phenyl)-dimethyl-silane 在 正丁基锂 、 ammonium cerium(IV) nitrate 、 偶氮二异丁腈 、 Celite 、 三正丁基氢锡 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 、 乙腈 、 苯 为溶剂， 反应 2.0h， 生成 ((1R,3S)-3-But-3-enyl-cyclohexyloxy)-(4-methoxy-phenyl)-dimethyl-silane
  参考文献：
  名称：

  The Study of the Kinetics of Intramolecular Radical Cyclizations of Acylsilanes via the Intramolecular Competition Method

  摘要：

  The kinetics of the radical cyclizations of acylsilanes is probed by the construction of an intramolecular competition system. In this system, known rate constants of olefin cyclizations are used as the internal clock. At-benzene reflux temperature (80 degrees C), the cyclization rate constants for 5-exo cyclizations of acylsilanes with primary radicals are on the order of 10(6) s(-1). The corresponding rate constants for 5-exo cyclizations with secondary radicals and 6-exo cyclizations with primary radicals lie on the order of 10(5) s(-1). The 6-exo cyclizations of acylsilanes with secondary radicals are slower and fall in the range of 10(4) s(-1). Substituents on the silicon of the acylsilanes affect the rates of cyclization. Large silyl groups reduce the rate, and this is more serious for the g-exo type of cyclizations. Electron-withdrawing groups increase the rates of cyclization.

  DOI：

  10.1021/jo982079k
• 作为产物：
  描述：

  1,3-二噻烷 、 chlorodimethyl(4-methoxyphenyl)silane 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 生成 [1,3]Dithian-2-yl-(4-methoxy-phenyl)-dimethyl-silane
  参考文献：
  名称：

  The Scope and Limitations of Intramolecular Radical Cyclizations of Acylsilanes with Alkyl, Aryl, and Vinyl Radicals

  摘要：

  5-Exo cyclizations of primary and secondary radicals with acylsilanes successfully give cyclopentyl silyl ethers. The corresponding 6-exo cyclizations are sensitive to changes of the size of silyl groups. Secondary radicals undergo 6-exo cyclizations with acylsilanes more slowly. Reaction of aryl radical with acylsilane proceeds well for 5-exo cyclization but not for 6-exo cyclization. Vinyl radicals give best results in 5-exo cyclizations with acylsilanes but give low yields (similar to 30%) in 6-exo cyclizations. Intramolecular cyclizations of vinyl radicals with acylsilanes give enol silyl ethers regiospecifically.

  DOI：

  10.1021/jo9711302