2-[2-(3,4-Bis-trimethylsilanyl-bicyclo[4.2.0]octa-1,3,5-trien-7-yl)-ethyl]-4-methylene-cyclopentane-1,1-dicarboxylic acid dimethyl ester | 124765-04-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-[2-(3,4-Bis-trimethylsilanyl-bicyclo[4.2.0]octa-1,3,5-trien-7-yl)-ethyl]-4-methylene-cyclopentane-1,1-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl 2-[2-[3,4-bis(trimethylsilyl)-7-bicyclo[4.2.0]octa-1,3,5-trienyl]ethyl]-4-methylidenecyclopentane-1,1-dicarboxylate
• CAS: 124765-04-4
• 化学式: C₂₆H₄₀O₄Si₂
• 分子量: 472.772
• InChiKey: UQDYBEFEIHFSEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-[2-(3,4-Bis-trimethylsilanyl-bicyclo[4.2.0]octa-1,3,5-trien-7-yl)-ethyl]-4-methylene-cyclopentane-1,1-dicarboxylic acid dimethyl ester 以 癸烷 为溶剂， 反应 10.0h， 以8%的产率得到dimethyl (1S,10R,13R)-6,7-bis(trimethylsilyl)tetracyclo[11.2.1.01,10.04,9]hexadeca-4,6,8-triene-14,14-dicarboxylate
  参考文献：
  名称：

  A stereoselective access to the basic skeleton of phyllocladane type diterpenes: [3+2], [2+2+2], and [4+2] cycloaddition

  摘要：

  DOI：

  10.1016/s0040-4039(01)80445-7
• 作为产物：
  描述：

  dimethyl 4-methylidene-2-[6-trimethylsilyl-3-(2-trimethylsilylethynyl)hex-5-ynyl]cyclopentane-1,1-dicarboxylate 在 carbon monoxide,cobalt,cyclopenta-1,3-diene potassium fluoride 作用下， 以 二甲基亚砜 为溶剂， 反应 4.5h， 生成 2-[2-(3,4-Bis-trimethylsilanyl-bicyclo[4.2.0]octa-1,3,5-trien-7-yl)-ethyl]-4-methylene-cyclopentane-1,1-dicarboxylic acid dimethyl ester
  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