methyl (1S,4аR,5S,8аR)-1,4а-dimethyl-6-methylidene-5-(2-{2-[(4-methylphenylsulfonamido)methyl]furan-3-yl}ethyl)decahydronaphthalene-1-carboxylate | 1400771-42-7

• 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: methyl (1S,4аR,5S,8аR)-1,4а-dimethyl-6-methylidene-5-(2-{2-[(4-methylphenylsulfonamido)methyl]furan-3-yl}ethyl)decahydronaphthalene-1-carboxylate
• CAS: 1400771-42-7
• 化学式: C₂₉H₃₉NO₅S
• 分子量: 513.698
• InChiKey: XQJPFWLADDVQAR-MXECZNPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.95
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  85.61
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (1S,4аR,5S,8аR)-1,4а-dimethyl-6-methylidene-5-(2-{2-[(4-methylphenylsulfonamido)methyl]furan-3-yl}ethyl)decahydronaphthalene-1-carboxylate 在 gold(III) chloride 、 potassium carbonate 作用下， 以 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 48.0h， 生成 methyl (1S,4аR,5S,8аR)-5-[2-(7-hydroxy-2-tosylisoindolin-4-yl)ethyl]-1,4а-dimethyl-6-methylidenedecahydronaphthalene-1-carboxylate
  参考文献：
  名称：

  Synthetic transformations of higher terpenoids: XXIX. Gold catalyzed cycloisomerization of propargylaminomethyl substituted and propargyloxymethyl substituted furanolabdanoids

  摘要：

  16-Propargylaminomethyl substituted and 16-propargyloxymethyl substituted furanolabdanoids were synthesized, which under the action of AuCl3 in acetonitrile underwent cycloisomerization forming 7-hydroxyisoindolines or 7-hydroxydihydroisobenzofurans substituted by a terpenoid fragment.

  DOI：

  10.1134/s1070428012080088
• 作为产物：
  描述：

  (1S,4aR,5S,8aR)-methyl 5-{2-[2-(aminomethyl)furan-3-yl]ethyl}-1,4a-dimethyl-6-methylene-decahydronaphthalene-1-carboxylate 、 对甲苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以93%的产率得到methyl (1S,4аR,5S,8аR)-1,4а-dimethyl-6-methylidene-5-(2-{2-[(4-methylphenylsulfonamido)methyl]furan-3-yl}ethyl)decahydronaphthalene-1-carboxylate
  参考文献：
  名称：

  Synthetic transformations of higher terpenoids: XXIX. Gold catalyzed cycloisomerization of propargylaminomethyl substituted and propargyloxymethyl substituted furanolabdanoids

  摘要：

  16-Propargylaminomethyl substituted and 16-propargyloxymethyl substituted furanolabdanoids were synthesized, which under the action of AuCl3 in acetonitrile underwent cycloisomerization forming 7-hydroxyisoindolines or 7-hydroxydihydroisobenzofurans substituted by a terpenoid fragment.

  DOI：

  10.1134/s1070428012080088