dimethyl (3R,4aR,4bR,8R,8aR,10aS,11R,12R)-2-isopropyl-4b,8-dimethyl-11-(3-methylureido)-4,4a,4b,5,6,7,8,8a,9,10-decahydro-3H-3,10a-ethanophenanthrene-8,12-dicarboxylate | 1160170-65-9

• 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: dimethyl (3R,4aR,4bR,8R,8aR,10aS,11R,12R)-2-isopropyl-4b,8-dimethyl-11-(3-methylureido)-4,4a,4b,5,6,7,8,8a,9,10-decahydro-3H-3,10a-ethanophenanthrene-8,12-dicarboxylate
• CAS: 1160170-65-9
• 化学式: C₂₇H₄₂N₂O₅
• 分子量: 474.641
• InChiKey: ILYRSMUBSCSCJX-GBUJBJQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  34.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  93.73
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  dimethyl (3R,4aR,4bR,8R,8aR,10aS,11R,12R)-2-isopropyl-4b,8-dimethyl-11-(3-methylureido)-4,4a,4b,5,6,7,8,8a,9,10-decahydro-3H-3,10a-ethanophenanthrene-8,12-dicarboxylate 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以68%的产率得到methyl (4aS,7R,10aR,12aR)-4b,12-(13-isopropyletheno)-2,7,10a-trimethyl-1,3-dioxooctadecahydronaphtho[1,2-h]quinazoline-7-carboxylate
  参考文献：
  名称：

  Synthetic transformations of higher terpenoids: XX. Synthesis and transformations of diterpene ureido esters

  摘要：

  Lossen rearrangement of N-hydroxymaleopimaric acid amide p-toluenesulfonate in the presence of amines in methanol led to the formation of the corresponding diterpene ureido esters with high regio- and stereoselectivity. Treatment of the resulting ureides with phosphoryl chloride gave cyclic amidines via intramolecular ring closure. Substituted hydantoins were obtained by reactions of the ureido esters with glyoxal in acid medium, and their treatment with sodium ethoxide in ethanol afforded compounds of the naphtho[1,2-h]-quinazoline series.

  DOI：

  10.1134/s1070428010080051
• 作为产物：
  描述：

  甲醇 、 methyl (3aR,6R,9aR,11aR)-3b,11-(12-isopropyletheno)-6,9a-dimethyl-2-(4-methylphenylsulfonyloxy)-1,3-dioxohexadecahydro-1H-naphtho[2,1-e]isoindole-6-carboxylate 、 甲胺 反应 1.0h， 生成 methyl (3aR,6R,9aR,11aR)-2-hydroxy-3b,11-(12-isopropyletheno)-6,9a-dimethyl-1,3-dioxohexadecahydro-1H-naphtho[2,1-e]isoindole-6-carboxylate 、 dimethyl (3R,4aR,4bR,8R,8aR,10aS,11R,12R)-2-isopropyl-4b,8-dimethyl-11-(3-methylureido)-4,4a,4b,5,6,7,8,8a,9,10-decahydro-3H-3,10a-ethanophenanthrene-8,12-dicarboxylate
  参考文献：
  名称：

  Synthetic transformations of higher terpenoids: XX. Synthesis and transformations of diterpene ureido esters

  摘要：

  Lossen rearrangement of N-hydroxymaleopimaric acid amide p-toluenesulfonate in the presence of amines in methanol led to the formation of the corresponding diterpene ureido esters with high regio- and stereoselectivity. Treatment of the resulting ureides with phosphoryl chloride gave cyclic amidines via intramolecular ring closure. Substituted hydantoins were obtained by reactions of the ureido esters with glyoxal in acid medium, and their treatment with sodium ethoxide in ethanol afforded compounds of the naphtho[1,2-h]-quinazoline series.

  DOI：

  10.1134/s1070428010080051