(1R,4S,7S,1'R,2'R,5'R)-7-<<2'-<1''-<(benzyloxy)methyl>ethenyl>-5'-methylcyclopentyl>methyl>-7-(methoxymethyl)bicyclo<2.2.1>hept-5-en-2-one | 133349-42-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,4S,7S,1'R,2'R,5'R)-7-<<2'-<1''-<(benzyloxy)methyl>ethenyl>-5'-methylcyclopentyl>methyl>-7-(methoxymethyl)bicyclo<2.2.1>hept-5-en-2-one
• CAS: 133349-42-5
• 化学式: C₂₆H₃₄O₃
• 分子量: 394.554
• InChiKey: ZIOCPFUDKMRAHL-KDYSXGEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  29.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,4S,7S,1'R,2'R,5'R)-7-<<2'-<1''-<(benzyloxy)methyl>ethenyl>-5'-methylcyclopentyl>methyl>-7-(methoxymethyl)bicyclo<2.2.1>hept-5-en-2-one 在 正丁基锂 、 韦德伊斯试剂 、 二异丙胺 作用下， 生成 (1R,3S,4S,7S,1'R,2'R,5'R)-7-<<2'-<1''-<(benzyloxy)methyl>ethenyl>-5'-methylcyclopentyl>methyl>-3-hydroxy-7-(methoxymethyl)bicyclo<2.2.1>hept-5-en-2-one 、 (1R,3R,4S,7S,1'R,2'R,5'R)-7-<<2'-<1''-<(benzyloxy)methyl>ethenyl>-5'-methylcyclopentyl>methyl>-3-hydroxy-7-(methoxymethyl)bicyclo<2.2.1>hept-5-en-2-one
  参考文献：
  名称：

  Studies on the synthesis of the diterpenoid mold metabolite sordaricin. Exploration of a prospective biogenetic intramolecular [4 + 2] cycloaddition

  摘要：

  In a model study directed toward the synthesis of the diterpenoid sordaricin 3, the main carbon skeleton was established via intramolecular [4 + 2] cycloadditions of the 5,5-cyclopentadienyl derivatives 24 and 30. These intermediates were prepared by two similar routes, beginning with the alkylation of either the norbornenyl ester 14 or its enantiomer with iodide 16. The oxygenated two-carbon bridge in each of the resulting adducts was then cut away by a sequence of oxidative processes to form the diene component for the cycloadditions. For 24 this began with the Bayer-Villiger oxidation (21 --> 22) and for 30, Vedejs alpha-hydroxylation of 27, followed by periodate cleavage. In the latter case, the benzyloxy group was introduced into the dienophile moiety by selective epoxidation of the isopropenyl group followed by amide-initiated elimination.

  DOI：

  10.1021/jo00011a027
• 作为产物：
  描述：

  (1R,2R,5R)-(2-isopropenyl-5-methylcyclopentyl)methanol 在 吡啶 、 C₆H₁₁N(i-Pr)Li 、 sodium hydride 、 碳酸氢钠 、 溶剂黄146 、 间氯过氧苯甲酸 、 红铝 、 lithium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 107.67h， 生成 (1R,4S,7S,1'R,2'R,5'R)-7-<<2'-<1''-<(benzyloxy)methyl>ethenyl>-5'-methylcyclopentyl>methyl>-7-(methoxymethyl)bicyclo<2.2.1>hept-5-en-2-one
  参考文献：
  名称：

  Studies on the synthesis of the diterpenoid mold metabolite sordaricin. Exploration of a prospective biogenetic intramolecular [4 + 2] cycloaddition

  摘要：

  In a model study directed toward the synthesis of the diterpenoid sordaricin 3, the main carbon skeleton was established via intramolecular [4 + 2] cycloadditions of the 5,5-cyclopentadienyl derivatives 24 and 30. These intermediates were prepared by two similar routes, beginning with the alkylation of either the norbornenyl ester 14 or its enantiomer with iodide 16. The oxygenated two-carbon bridge in each of the resulting adducts was then cut away by a sequence of oxidative processes to form the diene component for the cycloadditions. For 24 this began with the Bayer-Villiger oxidation (21 --> 22) and for 30, Vedejs alpha-hydroxylation of 27, followed by periodate cleavage. In the latter case, the benzyloxy group was introduced into the dienophile moiety by selective epoxidation of the isopropenyl group followed by amide-initiated elimination.

  DOI：

  10.1021/jo00011a027