Dimethyl <2-(ethylenedioxy)-4-<(trimethylsilyl)ethynyl>-1-hydroxy-7-(trimethylsilyl)-6-heptynyl>propanedioate | 132993-06-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: Dimethyl <2-(ethylenedioxy)-4-<(trimethylsilyl)ethynyl>-1-hydroxy-7-(trimethylsilyl)-6-heptynyl>propanedioate
• CAS: 132993-06-7
• 化学式: C₂₂H₃₆O₇Si₂
• 分子量: 468.695
• InChiKey: PDVOWYQTSNUYRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  31.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  91.29
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Dimethyl <2-(ethylenedioxy)-4-<(trimethylsilyl)ethynyl>-1-hydroxy-7-(trimethylsilyl)-6-heptynyl>propanedioate 在 palladium diacetate 、 carbon monoxide,cobalt,cyclopenta-1,3-diene potassium fluoride 、 三异丙基亚磷酸酯 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 癸烷 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 5.58h， 生成
  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 哌啶 、 草酰氯 、 ammonium cerium(IV) nitrate 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 水 、 甲苯 、 乙腈 为溶剂， 反应 50.67h， 生成 Dimethyl <2-(ethylenedioxy)-4-<(trimethylsilyl)ethynyl>-1-hydroxy-7-(trimethylsilyl)-6-heptynyl>propanedioate
  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