methyl 2-(methoxymethoxy)-2-methyldodecanoate | 1396787-78-2

• 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-(methoxymethoxy)-2-methyldodecanoate
• 英文别名: Methyl 2-(methoxymethoxy)-2-methyldodecanoate
• CAS: 1396787-78-2
• 化学式: C₁₆H₃₂O₄
• 分子量: 288.428
• InChiKey: GEYJKFRWRQNILO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-(methoxymethoxy)-2-methyldodecanoate 在 四甲基乙二胺 、 三氟甲磺酸三甲基硅酯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 2-Decyl-4-[dimethoxy(oxido)phosphaniumyl]-2-methyloxetan-3-one
  参考文献：
  名称：

  Method for the Efficient Synthesis of Highly-Substituted Oxetan- and Azetidin-, Dihydrofuran- and Pyrrolidin-3-ones and Its Application to the Synthesis of (±)-Pseudodeflectusin

  摘要：

  Highly substituted four- and five-membered heterocycles were prepared starting with O,P- and N,P-acetals by using a one-pot method involving base induced cyclization and a Horner-Wadsworth-Emmons (HWE) olefination reaction. Divergent synthesis of various heterocycles was achieved by using this method and transformations of the alkenyl group in the products of these processes were exemplified. Finally, a short and efficient synthesis of (+/-)-pseudodeflectusin based on the new methodology was achieved.

  DOI：

  10.1021/ol302096j
• 作为产物：
  描述：

  癸基溴 、 (S)-methyl 2-(methoxymethoxy)propanoate 在 正丁基锂 、 二异丙胺 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以84%的产率得到methyl 2-(methoxymethoxy)-2-methyldodecanoate
  参考文献：
  名称：

  Method for the Efficient Synthesis of Highly-Substituted Oxetan- and Azetidin-, Dihydrofuran- and Pyrrolidin-3-ones and Its Application to the Synthesis of (±)-Pseudodeflectusin

  摘要：

  Highly substituted four- and five-membered heterocycles were prepared starting with O,P- and N,P-acetals by using a one-pot method involving base induced cyclization and a Horner-Wadsworth-Emmons (HWE) olefination reaction. Divergent synthesis of various heterocycles was achieved by using this method and transformations of the alkenyl group in the products of these processes were exemplified. Finally, a short and efficient synthesis of (+/-)-pseudodeflectusin based on the new methodology was achieved.

  DOI：

  10.1021/ol302096j

文献信息

• Method for the Efficient Synthesis of Highly-Substituted Oxetan- and Azetidin-, Dihydrofuran- and Pyrrolidin-3-ones and Its Application to the Synthesis of (±)-Pseudodeflectusin
  作者：Tomohiro Maegawa、Kazuki Otake、Keiichi Hirosawa、Akihiro Goto、Hiromichi Fujioka

  DOI：10.1021/ol302096j

  日期：2012.9.21

  Highly substituted four- and five-membered heterocycles were prepared starting with O,P- and N,P-acetals by using a one-pot method involving base induced cyclization and a Horner-Wadsworth-Emmons (HWE) olefination reaction. Divergent synthesis of various heterocycles was achieved by using this method and transformations of the alkenyl group in the products of these processes were exemplified. Finally, a short and efficient synthesis of (+/-)-pseudodeflectusin based on the new methodology was achieved.