4-<(Trimethylsilyl)ethynyl>-1-(4-methoxyphenoxy)-7-(trimethylsilyl)-6-heptyn-2-one ethylene acetal | 132993-03-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-<(Trimethylsilyl)ethynyl>-1-(4-methoxyphenoxy)-7-(trimethylsilyl)-6-heptyn-2-one ethylene acetal
• CAS: 132993-03-4
• 化学式: C₂₄H₃₆O₄Si₂
• 分子量: 444.718
• InChiKey: OCCQOHHATLJLOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-<(Trimethylsilyl)ethynyl>-1-(4-methoxyphenoxy)-7-(trimethylsilyl)-6-heptyn-2-one ethylene acetal 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.17h， 以85%的产率得到2-(Ethylenedioxy)-4--7-(trimethylsilyl)-6-heptyn-1-ol
  参考文献：
  名称：

  Stereoselective access to the basic skeleton of tetracyclic diterpenes via a sequence of consecutive [3 + 2], [2 + 2 + 2], and [4 + 2] cycloaddition reactions

  摘要：

  Benzocyclobutenes 9a, 9b, 23, and 24, prepared from 1,5-hexadiyne in good yields in a sequence involving [3 + 2] annelation and [2 + 2 + 2] cycloaddition reactions, underwent an intramolecular [4 + 2] reaction to afford the basic skeleton of tetracyclic diterpenes phyllocladane and kaurane. The factors governing the stereochemistry of the Diels-Alder reaction have been elucidated. A carbonyl group at C-12 favored the kaurane stereochemistry (58:42) whereas acetal or silyl ether functions at that same position led to a highly (97:3) or totally stereoselective formation of the phyllocladane ring system.

  DOI：

  10.1021/jo00068a026
• 作为产物：
  描述：

  4-<(Trimethylsilyl)ethynyl>-1-(4-methoxyphenoxy)-7-(trimethylsilyl)-6-heptyn-2-ol 在 草酰氯 、 camphor-10-sulfonic acid 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 34.25h， 生成 4-<(Trimethylsilyl)ethynyl>-1-(4-methoxyphenoxy)-7-(trimethylsilyl)-6-heptyn-2-one ethylene acetal
  参考文献：
  名称：

  Stereoselective access to the basic skeleton of tetracyclic diterpenes via a sequence of consecutive [3 + 2], [2 + 2 + 2], and [4 + 2] cycloaddition reactions

  摘要：

  Benzocyclobutenes 9a, 9b, 23, and 24, prepared from 1,5-hexadiyne in good yields in a sequence involving [3 + 2] annelation and [2 + 2 + 2] cycloaddition reactions, underwent an intramolecular [4 + 2] reaction to afford the basic skeleton of tetracyclic diterpenes phyllocladane and kaurane. The factors governing the stereochemistry of the Diels-Alder reaction have been elucidated. A carbonyl group at C-12 favored the kaurane stereochemistry (58:42) whereas acetal or silyl ether functions at that same position led to a highly (97:3) or totally stereoselective formation of the phyllocladane ring system.

  DOI：

  10.1021/jo00068a026