(1R,4S,7S,1'R,2'R,5'R)-7-<<2'-<1''-(hydroxymethyl)ethenyl>-5'-methylcyclopentyl>methyl>-7-(methoxymethyl)bicyclo<2.2.1>hept-5-en-2-one | 133349-41-4

• 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: (1R,4S,7S,1'R,2'R,5'R)-7-<<2'-<1''-(hydroxymethyl)ethenyl>-5'-methylcyclopentyl>methyl>-7-(methoxymethyl)bicyclo<2.2.1>hept-5-en-2-one
• CAS: 133349-41-4
• 化学式: C₁₉H₂₈O₃
• 分子量: 304.43
• InChiKey: HNNJQSOJEHVNET-FPUJPIJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 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''-(hydroxymethyl)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 、 sodium hydride 、 二异丙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 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
  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 102.67h， 生成 (1R,4S,7S,1'R,2'R,5'R)-7-<<2'-<1''-(hydroxymethyl)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

文献信息

• Studies on the synthesis of the diterpenoid mold metabolite sordaricin. Exploration of a prospective biogenetic intramolecular [4 + 2] cycloaddition
  作者：Lewis N. Mander、Ralph P. Robinson

  DOI：10.1021/jo00011a027

  日期：1991.5

  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.