1-iodo-3,8,12,16-tetramethyl-3(E),7(E),11(E),15-heptadecatetraene | 140176-44-9

• 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: 1-iodo-3,8,12,16-tetramethyl-3(E),7(E),11(E),15-heptadecatetraene
• 英文别名: (6E,10E,14E)-17-iodo-2,6,10,15-tetramethylheptadeca-2,6,10,14-tetraene
• CAS: 140176-44-9
• 化学式: C₂₁H₃₅I
• 分子量: 414.413
• InChiKey: SMJHTOWXUVTKFV-USQNFQSVSA-N

物化性质

• 沸点：
  423.7±34.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.96
• 重原子数：
  22.0
• 可旋转键数：
  11.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  1-iodo-3,8,12,16-tetramethyl-3(E),7(E),11(E),15-heptadecatetraene 在 水 、 sodium chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 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
• 作为产物：
  描述：

  3,8,12,16-tetramethyl-3(E),7(E),11(E),15-heptadecatetraen-1-ol 在 吡啶 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 14.0h， 生成 1-iodo-3,8,12,16-tetramethyl-3(E),7(E),11(E),15-heptadecatetraene
  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

文献信息

• Efficient route to the synthesis of C-2, C-3 substituted 4-piperidones
  作者：Dharmpal S. Dodd、Allan C. Oehlschlager

  DOI：10.1016/s0040-4039(00)79755-3

  日期：1991.7

  6-dihydro-4-pyridone ((1) has proven to be exceptionally receptive in the conjugate addition of organocuprates to give C-2 substituted piperidones having the C-3 position activated toward alkylation. Enone (1) was used as the key synthon in the synthesis of C-1, C-2 and C-3 substituted 4-piperidinol (8).

  1-Carbobenzoxy-3-carbomethoxy-5,6-dihydro-4-pyridone（（1））已被证明在共轭添加有机铜酸盐时产生了C-3取代的C-2取代的哌啶酮，C-3位置朝着烷基化方向活化。烯酮（1）被用作合成C-1，C-2和C-3取代的4-哌啶醇的关键合成子（8）。