dimethyl pentacyclo<5.3.0.0^2,5.0^3,9.0^4,8>decane 2,5-dicarboxylate | 20440-77-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: dimethyl pentacyclo<5.3.0.0^2,5.0^3,9.0^4,8>decane 2,5-dicarboxylate
• 英文别名: Pentacyclo<5.3.0.0^2.5.0^3.9.0^4.8>decan-2,5-dicarbonsaeure-dimethylester；Dimethyl pentacyclo[5.3.0.02,5.03,9.04,8]decane-2,5-dicarboxylate
• CAS: 20440-77-1
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: YTZHXJZTWWCOIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl pentacyclo<5.3.0.0^2,5.0^3,9.0^4,8>decane 2,5-dicarboxylate 在 三甲基氯硅烷 、 potassium Sodium 、 叔丁醇 作用下， 生成 dimethyl tetracyclo<5.3.0.0^3,9.0^4,8>decane-endo-2,endo-5-dicarboxylate 、
  参考文献：
  名称：

  Thiele's ester as a reagent in organic synthesis. Preparation of pentacyclo[5.4.0.02,5.03,10.04,8]undecane-10-carboxylic acid

  摘要：

  Succinyl cleavage of the C(2)-C(5) sigma-bond in dimethyl pentacyclo[5.3.0.0(2,5).0(3,9).0(4,8)]decane-2,5-dicarboxylate, 2, afforded a tetracyclic diester, 3 (22-26%), along with two minor reaction products (4 and 5). Dieckmann condensation of 3 produced a mixture of 6a and 6b (67%). Wolff-Kishner reduction of the mixture of 6a and 6b thereby obtained afforded a mixture of products from which the title compound, 7b, could be isolated in 63% yield by fractional recrystallization. The structures of 3, 4 and 7b were established unequivocally via X-ray crystallographic methods,

  DOI：

  10.1016/s0040-4020(01)86340-7