methyl (Z)-(1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-{2-[2-(5-oxo-2-phenyl-4,5-dihydro-1,3-oxazol-4-ylidenemethyl)furan-3-yl]ethyl}decahydronaphthalene-1-carboxylate | 1027345-89-6

• 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: methyl (Z)-(1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-{2-[2-(5-oxo-2-phenyl-4,5-dihydro-1,3-oxazol-4-ylidenemethyl)furan-3-yl]ethyl}decahydronaphthalene-1-carboxylate
• 英文别名: methyl 15,16-epoxy-16-[(4Z)-5-oxo-2-phenyl-4,5-dihydro-1,3-oxazol-4-ylidenemethyl]labda-8(20),13(16),14-trien-19-oate
• CAS: 1027345-89-6
• 化学式: C₃₁H₃₅NO₅
• 分子量: 501.623
• InChiKey: CHEBQFOCFIPVRY-YGNXJXFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.51
• 重原子数：
  37.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  78.1
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl (Z)-(1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-{2-[2-(5-oxo-2-phenyl-4,5-dihydro-1,3-oxazol-4-ylidenemethyl)furan-3-yl]ethyl}decahydronaphthalene-1-carboxylate 在 ammonium hydroxide 、 sodium carbonate 作用下， 反应 14.0h， 以56%的产率得到methyl (1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-(2-{2-[(Z)-5-oxo-2-phenyl-4,5-dihydro-1H-imidazol-4-ylidenemethyl]furan-3-yl}ethyl)decahydronaphthalene-1-carboxylate
  参考文献：
  名称：

  Synthetic transformations of higher terpenoids: XV. Transformations of azlactone derived from 16-formyllambertianic acid methyl ester

  摘要：

  Condensation of 16-formyllambertianic acid methyl ester with hippuric acid gave methyl 15,16-epoxy-16-[(4Z)-5-oxo-2-phenyl-4,5-dihydrooxazol-4-ylidenemethyl]labda-8(20),13(16),14-trien-19-oate which underwent ready transformation into 2-benzoylamino-3-(2-furyl)acrylic acid of the labdanoid series. Reactions of the diterpenoid azlactone with amines and alpha-amino acid esters led to the formation of the corresponding carbamoylvinylbenzamides and N-(2-benzoylaminoacryloyl) amino acid esters, and furylacrylic acid hydrazides were formed in reactions with hydrazines. Cyclization of the N'-phenylhydrazide by the action of 1 M aqueous sodium hydroxide gave the corresponding 1,2,4-triazin-6-one. By treatment of the azlactone with aqueous ammonia on heating, 4-substituted 2-phenyl-4,5-dihydroimidazol-5-one was obtained.

  DOI：

  10.1134/s1070428007060073
• 作为产物：
  描述：

  马尿酸 、 methyl 16-formyllambertianate 在 potassium carbonate 作用下， 以 乙酸酐 为溶剂， 反应 5.0h， 以76%的产率得到methyl (Z)-(1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-{2-[2-(5-oxo-2-phenyl-4,5-dihydro-1,3-oxazol-4-ylidenemethyl)furan-3-yl]ethyl}decahydronaphthalene-1-carboxylate
  参考文献：
  名称：

  Synthetic transformations of higher terpenoids: XV. Transformations of azlactone derived from 16-formyllambertianic acid methyl ester

  摘要：

  Condensation of 16-formyllambertianic acid methyl ester with hippuric acid gave methyl 15,16-epoxy-16-[(4Z)-5-oxo-2-phenyl-4,5-dihydrooxazol-4-ylidenemethyl]labda-8(20),13(16),14-trien-19-oate which underwent ready transformation into 2-benzoylamino-3-(2-furyl)acrylic acid of the labdanoid series. Reactions of the diterpenoid azlactone with amines and alpha-amino acid esters led to the formation of the corresponding carbamoylvinylbenzamides and N-(2-benzoylaminoacryloyl) amino acid esters, and furylacrylic acid hydrazides were formed in reactions with hydrazines. Cyclization of the N'-phenylhydrazide by the action of 1 M aqueous sodium hydroxide gave the corresponding 1,2,4-triazin-6-one. By treatment of the azlactone with aqueous ammonia on heating, 4-substituted 2-phenyl-4,5-dihydroimidazol-5-one was obtained.

  DOI：

  10.1134/s1070428007060073