(3aS,6aS,1'R,2'R,5'R)-4-<<2'-(1''-methylethenyl)-5'-methylcyclopentyl>methyl>-4-(methoxymethyl)-2,3,3a,4-tetrahydro-6aH-cyclopentafuran-2-one | 133349-36-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3aS,6aS,1'R,2'R,5'R)-4-<<2'-(1''-methylethenyl)-5'-methylcyclopentyl>methyl>-4-(methoxymethyl)-2,3,3a,4-tetrahydro-6aH-cyclopentafuran-2-one
• 英文别名: (3aS,4S,6aR)-4-(methoxymethyl)-4-[[(1R,2R,5R)-2-methyl-5-prop-1-en-2-ylcyclopentyl]methyl]-3a,6a-dihydro-3H-cyclopenta[b]furan-2-one
• CAS: 133349-36-7
• 化学式: C₁₉H₂₈O₃
• 分子量: 304.43
• InChiKey: ZYFVFLRMVBXJCI-QCQTWIRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aS,6aS,1'R,2'R,5'R)-4-<<2'-(1''-methylethenyl)-5'-methylcyclopentyl>methyl>-4-(methoxymethyl)-2,3,3a,4-tetrahydro-6aH-cyclopentafuran-2-one 在 sodium periodate 、 lithium aluminium tetrahydride 、 正丁基锂 、 韦德伊斯试剂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 乙醚 、 水 、 甲苯 、 苯 为溶剂， 反应 39.17h， 生成 19-methoxy-14,15,16-trisnorsordaric-1-en-18-al
  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 、 sodium hydroxide 、 三氟化硼乙醚 、 双氧水 、 sodium hydride 、 溶剂黄146 、 红铝 、 lithium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 170.17h， 生成 (3aS,6aS,1'R,2'R,5'R)-4-<<2'-(1''-methylethenyl)-5'-methylcyclopentyl>methyl>-4-(methoxymethyl)-2,3,3a,4-tetrahydro-6aH-cyclopentafuran-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

• MANDER, LEWIS N.;ROBINSON, RALPH P., J. ORG. CHEM., 56,(1991) N1, C. 3595-3601
  作者：MANDER, LEWIS N.、ROBINSON, RALPH P.

  DOI：——

  日期：——