(3aR,4aS,8aR,9aR,E)-3-(3,4-dimethoxybenzylidene)-8a-methyl-5-methylidenedecahydronaphtho[2,3-b]furan-2(3H)-one | 1192803-30-7

• 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-(3,4-dimethoxybenzylidene)-8a-methyl-5-methylidenedecahydronaphtho[2,3-b]furan-2(3H)-one
• 英文别名: (3aR,4aS,8aR,9aR,E)-3-(4-dimethoxybenzylidene)-8a-methyl-5-methylenedecahydronaphtho[2,3-b]furan-2(3H)-one；(3E,3aR,4aS,8aR,9aR)-3-[(3,4-dimethoxyphenyl)methylidene]-8a-methyl-5-methylidene-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-2-one
• CAS: 1192803-30-7
• 化学式: C₂₃H₂₈O₄
• 分子量: 368.473
• InChiKey: DRDBBCMUVJQNBA-IDMHRFPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  异土木香内酯 、 4-碘藜芦醚 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， 反应 8.0h， 以81%的产率得到(3aR,4aS,8aR,9aR,E)-3-(3,4-dimethoxybenzylidene)-8a-methyl-5-methylidenedecahydronaphtho[2,3-b]furan-2(3H)-one
  参考文献：
  名称：

  Sesquiterpene metylenelactones in a palladium-catalyzed cross-coupling reaction

  摘要：

  DOI：

  10.1134/s001250080906007x

文献信息

• Synthetic transformations of sesquiterpene lactones 6. Alantolactone and isoalantolactone derivatives in the Heck reaction
  作者：E. E. Shul’ts、A. V. Belovodskii、M. M. Shakirov、G. A. Tolstikov

  DOI：10.1007/s11172-012-0274-4

  日期：2012.10

  the eudesman-type methylidenelactones (alantolactone, alloalantolactone, and 4,15-epoxyisoalantolactone) with haloarenes afforded the corresponding (E)-13-aryleudesma-4(15),11(13)-dien-8β,12-olides and 11-arylmethyl-13-noreudesma-4(15),7(11)-dien-8α,12-olides. The yields and the ratios of the arylation products depended on the reaction conditions and the structure of lactone. Certain side processes were

  eudesman 型亚甲基内酯（alantolactone、alloalantolactone 和 4,15-epoxyisoalantolactone）与卤代芳烃的 Heck 反应得到相应的 (E)-13-aryleudesma-4(15),11(13)-dien-8β,12- olides 和 11-arylmethyl-13-noreudesma-4(15),7(11)-dien-8α,12-olides。芳基化产物的产率和比例取决于反应条件和内酯的结构。发现发生了某些副过程。
• Synthetic transformations of methylenelactones of eudesmanic type. Behavior of isoalantolactone under the conitions of heck reaction
  作者：A. V. Belovodskii、E. E. Shults、M. M. Shakirov、I. Yu. Bagryanskaya、Yu. V. Gatilov、G. A. Tolstikov

  DOI：10.1134/s1070428010110199

  日期：2010.11

  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.