2-methylene-2,3-dihydrofuran | 82357-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 2-methylene-2,3-dihydrofuran
• 英文别名: 2-Methylen-2,3-dihydro-furan；Furan, 2,3-dihydro-2-methylene-；2-methylidene-3H-furan
• CAS: 82357-65-1
• 化学式: C₅H₆O
• 分子量: 82.102
• InChiKey: IRGVRURTPPUEDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-methylene-2,3-dihydrofuran 、 癸醛 在 2-甲基呋喃 、 zinc(II) chloride 作用下， 以 乙醚 为溶剂， 反应 0.5h， 以78%的产率得到1-(2-furyl)undecan-2-ol
  参考文献：
  名称：

  Kishner's Reduction of 2-Furylhydrazone Gives 2-Methylene-2,3-dihydrofuran, a Highly Reactive Ene in the Ene Reaction

  摘要：

  The Kishner reduction of 2-furylhydrazone gives 2-methylene-2,3-dihydrofuran as the major abnormal reduction product. 2-Methylene-2,3-dihydrofuran is an excellent ene in the carbonyl-ene reaction, reacting with a variety of aldehydes. Most notable was the asymmetric carbonyl-ene reaction of 2-methylene-2,3-dihydrofuran and decanal using Ti(OCH(CH3)(2))(4)/(S)-BINOL to give the corresponding alcohol in 66% yield and 94% ee. The reaction of 2-methylene-2,3-dihydrofuran with 2 equiv of 1,4-benzoquinone unexpectedly gave a monoalkylated 1,4-hydroquinone/1,4-benzoquinone electron donor-acceptor complex.

  DOI：

  10.1021/jo0479112
• 作为产物：
  描述：

  2-呋喃甲酰肼 在 potter's clay 、 铂 氢氧化钾 作用下， 生成 2-甲基呋喃 、 2-methylene-2,3-dihydrofuran
  参考文献：
  名称：

  Kishner's Reduction of 2-Furylhydrazone Gives 2-Methylene-2,3-dihydrofuran, a Highly Reactive Ene in the Ene Reaction

  摘要：

  The Kishner reduction of 2-furylhydrazone gives 2-methylene-2,3-dihydrofuran as the major abnormal reduction product. 2-Methylene-2,3-dihydrofuran is an excellent ene in the carbonyl-ene reaction, reacting with a variety of aldehydes. Most notable was the asymmetric carbonyl-ene reaction of 2-methylene-2,3-dihydrofuran and decanal using Ti(OCH(CH3)(2))(4)/(S)-BINOL to give the corresponding alcohol in 66% yield and 94% ee. The reaction of 2-methylene-2,3-dihydrofuran with 2 equiv of 1,4-benzoquinone unexpectedly gave a monoalkylated 1,4-hydroquinone/1,4-benzoquinone electron donor-acceptor complex.

  DOI：

  10.1021/jo0479112

文献信息

• Kishner, Zhurnal Obshchei Khimii, 1931, vol. 1, p. 1212,1216
  作者：Kishner

  DOI：——

  日期：——
• The Structure of Methylenedihydrofuran
  作者：Harold L. Rice

  DOI：10.1021/ja01132a529

  日期：1952.6
• Kishner's Reduction of 2-Furylhydrazone Gives 2-Methylene-2,3-dihydrofuran, a Highly Reactive Ene in the Ene Reaction
  作者：William H. Miles、Elizabeth A. Dethoff、Hannah H. Tuson、Gözde Ulas

  DOI：10.1021/jo0479112

  日期：2005.4.1

  The Kishner reduction of 2-furylhydrazone gives 2-methylene-2,3-dihydrofuran as the major abnormal reduction product. 2-Methylene-2,3-dihydrofuran is an excellent ene in the carbonyl-ene reaction, reacting with a variety of aldehydes. Most notable was the asymmetric carbonyl-ene reaction of 2-methylene-2,3-dihydrofuran and decanal using Ti(OCH(CH3)(2))(4)/(S)-BINOL to give the corresponding alcohol in 66% yield and 94% ee. The reaction of 2-methylene-2,3-dihydrofuran with 2 equiv of 1,4-benzoquinone unexpectedly gave a monoalkylated 1,4-hydroquinone/1,4-benzoquinone electron donor-acceptor complex.