2-(3,4-dimethoxyphenyl)-2,3-dihydrofuran | 124266-47-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3,4-dimethoxyphenyl)-2,3-dihydrofuran
• CAS: 124266-47-3
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: NOYHIEFOUGNVLM-UHFFFAOYSA-N

物化性质

• 沸点：
  299.0±40.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3,4-dimethoxyphenyl)-2,3-dihydrofuran 、 2-碘萘 以93%的产率得到
  参考文献：
  名称：

  LAROCK, RICHARD C.;GONG, WILLIAM H., J. ORG. CHEM., 55,(1990) N, C. 407-408

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(3,4-dimethoxy-phenyl)-but-3-yn-1-ol 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 tris(3,5-difluorophenyl)phosphine 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以74%的产率得到2-(3,4-dimethoxyphenyl)-2,3-dihydrofuran
  参考文献：
  名称：

  A Rh(I)-Catalyzed Cycloisomerization of Homo- and Bis-homopropargylic Alcohols

  摘要：

  The ability to form rhodium-vinylidene complexes in situ from terminal alkynes has led to the development of a catalytic process, the cycloisomerization of homopropargylic and bis-homopropargylic alcohols to dihydrofurans and dihydropyrans. Among the transition metals that perform similar reactions, rhodium catalysts demonstrate the best chemoselectivity and turnover numbers to date. Both secondary and tertiary alcohols participate equally well. The presence of proparylic oxygen and nitrogen functionality, which potentially can be induced to ionize via formation of allenylidene metal complexes, is compatible with this catalyst. The formation of a 5-amino-dihydropyran which is not compatible with some of the previous catalysts proceeds in good yield with the rhodium catalysts. A substrate bearing a benzylic hydroxyl group adjacent to an electron-rich aromatic ring also participates without complications of ionization. The method provides access to useful aminosugars. A mechanism to account for the different selectivity of this catalyst as compared to others is proposed.

  DOI：

  10.1021/ja0344258

文献信息

• Kinetic resolution of 2-substituted-2,3-dihydrofurans by a palladium-catalyzed asymmetric Heck reaction
  作者：Hao Li、Shi-Li Wan、Chang-Hua Ding、Bin Xu、Xue-Long Hou

  DOI：10.1039/c5ra17374d

  日期：——

  The kinetic resolution of 2-substituted-dihydrofurans via a Pd-catalyzed asymmetric Heck reaction was realized for the first time.

  通过Pd催化的不对称Heck反应，首次实现了对2-取代二氢呋喃的动力学分辨。
• Palladium-catalyzed synthesis of trans-2,5-diaryltetrahydrofurans, potent platelet-activating factor antagonists
  作者：Richard C. Larock、William H. Gong

  DOI：10.1021/jo00289a002

  日期：1990.1