1-(carbobenzyloxy)-2-<3,8,12,16-tetramethyl-3(E),7(E),11(E),15-heptadecatetraenyl>-4-piperidone | 140176-49-4

• 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: 1-(carbobenzyloxy)-2-<3,8,12,16-tetramethyl-3(E),7(E),11(E),15-heptadecatetraenyl>-4-piperidone
• 英文别名: 1-(carbobenzyloxy)-2-(3,8,12,16-tetramethyl-3(E),7(E),11(E),15-heptadecatetraenyl)-4-piperidone；benzyl 4-oxo-2-[(3E,7E,11E)-3,8,12,16-tetramethylheptadeca-3,7,11,15-tetraenyl]piperidine-1-carboxylate
• CAS: 140176-49-4
• 化学式: C₃₄H₄₉NO₃
• 分子量: 519.768
• InChiKey: UXBGVKIAWLZWBI-UAIXEQCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.28
• 重原子数：
  38.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-(carbobenzyloxy)-2-<3,8,12,16-tetramethyl-3(E),7(E),11(E),15-heptadecatetraenyl>-4-piperidone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以82%的产率得到1-methyl-2-[(3E,7E,11E)-3,8,12,16-tetramethylheptadeca-3,7,11,15-tetraenyl]piperidin-4-ol
  参考文献：
  名称：

  Synthesis of inhibitors of 2,3-oxidosqualene-lanosterol cyclase: conjugate addition of organocuprates to N-(carbobenzyloxy)-3-carbomethoxy-5,6-dihydro-4-pyridone.

  摘要：

  Synthesis of ammonium ion analogues of the first cationic intermediate, 5, presumed to be formed during the cyclization of 2,3-oxidosqualene by 2,3-oxidosqualene-lanosterol cyclase are reported. The required 2,3-substituted-4-piperidinols are prepared by conjugate addition of higher order alkyl (2-thienyl)(cyano)cuprates to 1-(carbobenzyloxy)-3-carbomethoxy-5,6-dihydro-4-pyridone. The nitrogen protecting group (carbobenzyloxy) is key to the synthesis in that it allows the conjugate addition to proceed in high yield and is easily converted to the required N-methyl group in the final products. The key terpenoid side chain appended to C-2 of the piperidinols was constructed from homofarnesyl bromide and 1,5-difunctionalized homoisopentenyl derivatives prepared by zirconium-catalyzed carboalumination of protected 1-butyn-4-ol.

  DOI：

  10.1021/jo00036a008
• 作为产物：
  描述：

  4-氧代-1,3-哌啶二羧酸 3-甲基 1-(苯基甲基)酯 在 水 、 双氧水 、 sodium hydride 、 sodium chloride 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 反应 9.75h， 生成 1-(carbobenzyloxy)-2-<3,8,12,16-tetramethyl-3(E),7(E),11(E),15-heptadecatetraenyl>-4-piperidone
  参考文献：
  名称：

  Synthesis of inhibitors of 2,3-oxidosqualene-lanosterol cyclase: conjugate addition of organocuprates to N-(carbobenzyloxy)-3-carbomethoxy-5,6-dihydro-4-pyridone.

  摘要：

  Synthesis of ammonium ion analogues of the first cationic intermediate, 5, presumed to be formed during the cyclization of 2,3-oxidosqualene by 2,3-oxidosqualene-lanosterol cyclase are reported. The required 2,3-substituted-4-piperidinols are prepared by conjugate addition of higher order alkyl (2-thienyl)(cyano)cuprates to 1-(carbobenzyloxy)-3-carbomethoxy-5,6-dihydro-4-pyridone. The nitrogen protecting group (carbobenzyloxy) is key to the synthesis in that it allows the conjugate addition to proceed in high yield and is easily converted to the required N-methyl group in the final products. The key terpenoid side chain appended to C-2 of the piperidinols was constructed from homofarnesyl bromide and 1,5-difunctionalized homoisopentenyl derivatives prepared by zirconium-catalyzed carboalumination of protected 1-butyn-4-ol.

  DOI：

  10.1021/jo00036a008