5,5-Diethyl-4-phenyl-dihydro-furan-2-one | 188646-70-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 5,5-Diethyl-4-phenyl-dihydro-furan-2-one
• 英文别名: 2(3H)-Furanone, 5,5-diethyldihydro-4-phenyl-；5,5-diethyl-4-phenyloxolan-2-one
• CAS: 188646-70-0
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: LIMVIMKOVVLRDR-UHFFFAOYSA-N

物化性质

• 沸点：
  352.5±31.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  5,5-Diethyl-4-phenyl-tetrahydro-furan-2-ol 在 silver carbonate 作用下， 以 甲苯 为溶剂， 以78%的产率得到5,5-Diethyl-4-phenyl-dihydro-furan-2-one
  参考文献：
  名称：

  Diastereoselective Synthesis of Highly Substituted Five-Membered-Ring Oxygen Heterocycles by Zirconocene-Mediated C-C Coupling Reactions

  摘要：

  As homoenolate equivalents, zirconocene-1-aza-1,3-diene complexes were used for the first time in stereoselective synthesis. By insertion of an unsymmetrical ketone in the Zr-C σ bond, sterically demanding trisubstituted dihydro- and tetrahydrofuran derivatives were prepared in good overall yields and with high diastereoselectivities (see below).

  DOI：

  10.1002/(sici)1521-3773(19980703)37:12<1673::aid-anie1673>3.0.co;2-a

文献信息

• Direct generation of lithium homoenolates from 3-aryl α,β-unsaturated ketones or esters by an arene-catalysed lithiation: Synthesis of substituted tetrahydrofurans and γ-butyrolactones
  作者：Emma Alonso、Diego J. Ramón、Miguel Yus

  DOI：10.1016/s0040-4020(96)01155-6

  日期：1997.2

  The reaction of α,β-unsaturated ketones 1 with an excess of lithium powder, a catalytic amount of naphthalene (4 %) and different carbonyl compounds in the presence of boron trifluoride in THF at −78 – 0°C yields, after treatament with silyl nucleophile and final hydrolysis, the expected substituted tetrahydrofurans 5. Similar methodology applied to β-aryl acrylic esters 6, but without using boron trifluoride

  α-β-不饱和酮1与过量的锂粉，催化量的萘（4％）和不同的羰基化合物在三氟化硼存在下于THF中在-78 – 0°C下反应，用•甲硅烷基亲核试剂和最终水解，预期取代的四氢呋喃5。将类似的方法应用于β-芳基丙烯酸酯6，但不使用三氟化硼或甲硅烷基试剂，则可得到相应的内酯7。
• Diastereoselective Synthesis of Highly Substituted Five-Membered-Ring Oxygen Heterocycles by Zirconocene-Mediated C-C Coupling Reactions
  作者：Dieter Enders、Manfred Kroll、Gerhard Raabe、Jan Runsink

  DOI：10.1002/(sici)1521-3773(19980703)37:12<1673::aid-anie1673>3.0.co;2-a

  日期：1998.7.3

  As homoenolate equivalents, zirconocene-1-aza-1,3-diene complexes were used for the first time in stereoselective synthesis. By insertion of an unsymmetrical ketone in the Zr-C σ bond, sterically demanding trisubstituted dihydro- and tetrahydrofuran derivatives were prepared in good overall yields and with high diastereoselectivities (see below).