4-<(Trimethylsilyl)ethynyl>-1-(4-methoxyphenoxy)-7-(trimethylsilyl)-6-heptyn-2-ol | 132993-01-2

• 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-ol
• CAS: 132993-01-2
• 化学式: C₂₂H₃₄O₃Si₂
• 分子量: 402.681
• InChiKey: XDKHHTCHDRSDFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-<(Trimethylsilyl)ethynyl>-1-(4-methoxyphenoxy)-7-(trimethylsilyl)-6-heptyn-2-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 4-<(Trimethylsilyl)ethynyl>-1-(4-methoxyphenoxy)-7-(trimethylsilyl)-6-heptyn-2-one
  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：

  2,3-环氧丙基-4-甲氧基苯基醚 、 1,6-bis(trimethylsilyl)-1,5-hexadiyne 在 正丁基锂 、 四甲基乙二胺 作用下， 生成 4-<(Trimethylsilyl)ethynyl>-1-(4-methoxyphenoxy)-7-(trimethylsilyl)-6-heptyn-2-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