Methyl 2,2-dimethyltridec-12-enoate | 231629-10-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Methyl 2,2-dimethyltridec-12-enoate
• CAS: 231629-10-0
• 化学式: C₁₆H₃₀O₂
• 分子量: 254.413
• InChiKey: AIKNFQNOJJPPMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Methyl 2,2-dimethyltridec-12-enoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以55%的产率得到2,2-dimethyl-12-tridecen-1-ol
  参考文献：
  名称：

  Synthesis of Sterically Hindered Long-Chain Alkenols via Organolithium Compounds.

  摘要：

  The synthesis of sterically hindered primary, secondary and tertiary alcohols is reported. An unusual monoalkylation/reduction occurs on treatment of a fully alpha-substituted methyl carboxylate with t-BuLi. A mechanism not involving a ketone intermediate but a beta-H abstraction from t-BuLi prior to or after alkylation is proposed.

  DOI：

  10.3891/acta.chem.scand.53-0352
• 作为产物：
  描述：

  异丁酸甲酯 、 11-溴-1-十一烯 在 lithium diisopropyl amide 作用下， 以80%的产率得到Methyl 2,2-dimethyltridec-12-enoate
  参考文献：
  名称：

  Synthesis of Sterically Hindered Long-Chain Alkenols via Organolithium Compounds.

  摘要：

  The synthesis of sterically hindered primary, secondary and tertiary alcohols is reported. An unusual monoalkylation/reduction occurs on treatment of a fully alpha-substituted methyl carboxylate with t-BuLi. A mechanism not involving a ketone intermediate but a beta-H abstraction from t-BuLi prior to or after alkylation is proposed.

  DOI：

  10.3891/acta.chem.scand.53-0352

文献信息

• Synthesis of Sterically Hindered Long-Chain Alkenols via Organolithium Compounds.
  作者：T. Tuulamari Helaja、Barbro Löfgren、Tapio Hase、Lars Skattebøl、Eirik Sundby、Carsten Christophersen、Hong-Gen Wang、Xin-Kan Yao、Hong-Gen Wang、J. -P. Tuchagues、Mattias Ögren

  DOI：10.3891/acta.chem.scand.53-0352

  日期：——

  The synthesis of sterically hindered primary, secondary and tertiary alcohols is reported. An unusual monoalkylation/reduction occurs on treatment of a fully alpha-substituted methyl carboxylate with t-BuLi. A mechanism not involving a ketone intermediate but a beta-H abstraction from t-BuLi prior to or after alkylation is proposed.