(E)-2-Methyl-1-(phenyldimethylsilyl)-4-<(p-toluenesulfonyl)oxy>-1-butene | 168132-13-6

• 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: (E)-2-Methyl-1-(phenyldimethylsilyl)-4-<(p-toluenesulfonyl)oxy>-1-butene
• 英文别名: [(E)-4-[dimethyl(phenyl)silyl]-3-methylbut-3-enyl] 4-methylbenzenesulfonate
• CAS: 168132-13-6
• 化学式: C₂₀H₂₆O₃SSi
• 分子量: 374.576
• InChiKey: MFBZOVSLFSMPTI-FBMGVBCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-Methyl-1-(phenyldimethylsilyl)-4-<(p-toluenesulfonyl)oxy>-1-butene 在 铜 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 丙酮 为溶剂， 反应 19.83h， 生成 (1E,7E/Z)-5-Acetyl-2,8-dimethyl-1-(phenyldimethylsilyl)-1,7,9-decatriene
  参考文献：
  名称：

  Phenyldimethylsilyl as an Alcohol Surrogate in Intramolecular Diels-Alder Cycloaddition: Synthesis of .alpha.-Dictyopterol

  摘要：

  alpha-Dictyopterol (1a), a sesquiterpene isolated from the essential oil of Dicytopteris divaricata, has been synthesized from bicyclic ketone 2, obtained by thermal cyclization of triene intermediate 11. The key observation is that the phenyldimethylsilyl group, a surrogate for hydroxyl, does not interfere with the internal Diels-Alder cycloaddition.

  DOI：

  10.1021/jo00122a038
• 作为产物：
  描述：

  (E)-2-Methyl-1-(phenyldimethylsilyl)-4-(tetrahydropyranyloxy)-1-butene 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 (E)-2-Methyl-1-(phenyldimethylsilyl)-4-<(p-toluenesulfonyl)oxy>-1-butene
  参考文献：
  名称：

  Phenyldimethylsilyl as an Alcohol Surrogate in Intramolecular Diels-Alder Cycloaddition: Synthesis of .alpha.-Dictyopterol

  摘要：

  alpha-Dictyopterol (1a), a sesquiterpene isolated from the essential oil of Dicytopteris divaricata, has been synthesized from bicyclic ketone 2, obtained by thermal cyclization of triene intermediate 11. The key observation is that the phenyldimethylsilyl group, a surrogate for hydroxyl, does not interfere with the internal Diels-Alder cycloaddition.

  DOI：

  10.1021/jo00122a038

文献信息

• Phenyldimethylsilyl as an Alcohol Surrogate in Intramolecular Diels-Alder Cycloaddition: Synthesis of .alpha.-Dictyopterol
  作者：Douglass F. Taber、Rama S. Bhamidipati、Larry Yet

  DOI：10.1021/jo00122a038

  日期：1995.9

  alpha-Dictyopterol (1a), a sesquiterpene isolated from the essential oil of Dicytopteris divaricata, has been synthesized from bicyclic ketone 2, obtained by thermal cyclization of triene intermediate 11. The key observation is that the phenyldimethylsilyl group, a surrogate for hydroxyl, does not interfere with the internal Diels-Alder cycloaddition.