4-benzylidene-2-methyl-2-(3-phenylpropyl)oxetan-3-one | 1396787-34-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 4-benzylidene-2-methyl-2-(3-phenylpropyl)oxetan-3-one
• 英文别名: (4Z)-4-benzylidene-2-methyl-2-(3-phenylpropyl)oxetan-3-one
• CAS: 1396787-34-0
• 化学式: C₂₀H₂₀O₂
• 分子量: 292.378
• InChiKey: VEVVQRHOFXEPSZ-SDXDJHTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl 2-(methoxymethoxy)-2-methyl-5-phenylpentanoate 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 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 4-benzylidene-2-methyl-2-(3-phenylpropyl)oxetan-3-one 、 4-benzylidene-2-methyl-2-(3-phenylpropyl)oxetan-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

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.