(3Z,3aR,4aS,8aR,9aR)-3-[(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)methylidene]-8a-methyl-5-methylidenedodecahydronaphtho-[2,3-b]furan-2-one | 1523436-81-8

• 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: (3Z,3aR,4aS,8aR,9aR)-3-[(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)methylidene]-8a-methyl-5-methylidenedodecahydronaphtho-[2,3-b]furan-2-one
• 英文别名: (3z,3Ar,4as,8ar,9ar)-3-[(1,3-dimethyl-2,4-di-oxo-1,2,3,4-tetrahydropyrimidin-5-yl)methylidene]-8a-methyl-5-methylidenedodecahydronaphtho-[2,3-b]furan-2-one；5-[(Z)-[(3aR,4aS,8aR,9aR)-8a-methyl-5-methylidene-2-oxo-3a,4,4a,6,7,8,9,9a-octahydrobenzo[f][1]benzofuran-3-ylidene]methyl]-1,3-dimethylpyrimidine-2,4-dione
• CAS: 1523436-81-8
• 化学式: C₂₁H₂₆N₂O₄
• 分子量: 370.448
• InChiKey: AFCWJFKSBFWUJZ-CTNLLNHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  66.9
• 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 、 5-碘-1,3-的甲基尿嘧啶 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58%的产率得到(3E,3aR,4aS,8aR,9aR)-3-[(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)methylidene]-8a-methyl-5-methylidenedodecahydronaphtho-[2,3-b]furan-2-one
  参考文献：
  名称：

  Synthetic transformations of sesquiterpene lactones: VII. Palladium-catalyzed cross-coupling of isoalantolactone with 5-halouracils

  摘要：

  Palladium-catalyzed cross-coupling of isoalantolactone with 1,3-disubstituted or 1-substituted 5-bromo(iodo)uracils afforded mainly (13E)-13-(2,4-dioxotetrahydropyrimidin-5-yl)eudesma-4(15),11(13)-dien-8 beta,12-olides whose yields depended on the composition of the catalytic system, base, and additive. The structure of (13E)-13-[3-(2-cyanoethyl)-2,4-dioxotetrahydropyrimidin-5-yl]eudesma-4(15),11(13)-dien-8 beta,12-olide was proved by X-ray analysis.

  DOI：

  10.1134/s1070428013120130

文献信息

• Synthetic transformations of sesquiterpene lactones: VII. Palladium-catalyzed cross-coupling of isoalantolactone with 5-halouracils
  作者：S. S. Patrushev、M. M. Shakirov、T. V. Rybalova、E. E. Shul’ts

  DOI：10.1134/s1070428013120130

  日期：2013.12

  Palladium-catalyzed cross-coupling of isoalantolactone with 1,3-disubstituted or 1-substituted 5-bromo(iodo)uracils afforded mainly (13E)-13-(2,4-dioxotetrahydropyrimidin-5-yl)eudesma-4(15),11(13)-dien-8 beta,12-olides whose yields depended on the composition of the catalytic system, base, and additive. The structure of (13E)-13-[3-(2-cyanoethyl)-2,4-dioxotetrahydropyrimidin-5-yl]eudesma-4(15),11(13)-dien-8 beta,12-olide was proved by X-ray analysis.