(3aR,4aS,8aR,9aR,E)-3-(3-methyl-4-fluorobenzylidene)-8a-methyl-5-methylidenedecahydronaphtho[2,3-b]furan-2(3H)-one | 1265907-76-3

• 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: (3aR,4aS,8aR,9aR,E)-3-(3-methyl-4-fluorobenzylidene)-8a-methyl-5-methylidenedecahydronaphtho[2,3-b]furan-2(3H)-one
• 英文别名: (3Ar,4as,8ar,9ar,e)-3-(3-methyl-4-fluoro-benzylidene)-8a-methyl-5-methylidenedeca-hydronaphtho[2,3-b]-furan-2(3h)-one；(3E,3aR,4aS,8aR,9aR)-3-[(4-fluoro-3-methylphenyl)methylidene]-8a-methyl-5-methylidene-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one
• CAS: 1265907-76-3
• 化学式: C₂₂H₂₅FO₂
• 分子量: 340.438
• InChiKey: SLNDLOMACRMRSW-QELVUWCGSA-N

物化性质

• 熔点：
  188-191 °C
• 沸点：
  486.2±45.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异土木香内酯 、 2-氟-5-碘甲苯 在 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以57%的产率得到(3aR,4aS,8aR,9aR,E)-3-(3-methyl-4-fluorobenzylidene)-8a-methyl-5-methylidenedecahydronaphtho[2,3-b]furan-2(3H)-one
  参考文献：
  名称：

  Synthetic transformations of methylenelactones of eudesmanic type. Behavior of isoalantolactone under the conitions of heck reaction

  摘要：

  By Heck reaction of isoalantolactone with aryl bromides or aryl iodides (3aR,4aS,8aR,9aR,E)-3-arylmethylidene-8a-methyl-5-methylidenedecahydronaphtho[2,3-b]furan-2(3H)-ones and (4aS,8aR,9aS)-3-arylmethyl-8a-methyl-5-methylidene-4a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(4H)-ones, products of the double bond shift, were synthesized. The yields of the arylation products depend on the nature of the catalytic system and on the structure of the aryl halide. The structures of(3aR,4aS,8aR,9aR,E)-3-(3,4-dimethoxybenzylidene)-8a-methyl-5-methylidenedecahydronaphtho[2,3-b] furan-2(3H)-one and (4aS,8aR,9aS)-3-(2-methylsulfanylbenzyl)-8a-methyl-5-methylidene-4a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(4H)-one were proved by XRD analysis.

  DOI：

  10.1134/s1070428010110199