2,3-dihydrofuran-3-ol | 65904-34-9

• 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: 2,3-dihydrofuran-3-ol
• CAS: 65904-34-9
• 化学式: C₄H₆O₂
• 分子量: 86.0904
• InChiKey: DRNQVMIOXGNQTM-UHFFFAOYSA-N

物化性质

• 沸点：
  178.0±39.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丙酰氯 、 2,3-dihydrofuran-3-ol 在 4-二甲氨基吡啶 、 正丁基锂 、 1,10-菲罗啉 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.08h， 生成 2,3-Dihydrofuran-3-yl propanoate
  参考文献：
  名称：

  Stereochemical control in the ester enolate Claisen rearrangement. 2. Chairlike vs boatlike transition-state selection

  摘要：

  The preference for chair- and boatlike transition-state geometries in the ester enolate Claisen rearrangement of straight chain, carbocyclic, and heterocyclic propanoates was investigated. A novel stereoelectronic effect in pyranoid and furanoid glycal systems leads to a significant relative stabilization of the boatlike vs the chairlike TS double-ended-dagger. The preferred transition state in six- and five-membered carbocyclic systems is highly dependent on steric factors, as the energy difference between chair- and boatlike TS double-ended-dagger tends to be small. With straight-chain substrates, a significant contribution of the boatlike TS double-ended-dagger to the rearrangement product mixture is only expected in bis-donor substituted allylic esters.

  DOI：

  10.1021/jo00011a023

文献信息

• Notable temperature effect on the stereoselectivity in the photochemical [2+2] cycloaddition reaction (Paternò–Büchi reaction) of 2,3-dihydrofuran-3-ol derivatives with benzophenone
  作者：Manabu Abe、Midori Terazawa、Koichi Nozaki、Araki Masuyama、Takashi Hayashi

  DOI：10.1016/j.tetlet.2006.02.046

  日期：2006.4

  A notable temperature effect (nonlinear Eyring plot) on stereoselectivity, trans-configured oxetane 2 versus cis-configured oxetane 2, is reported in the photochemical [2+2] cycloaddition reaction (Paternò–Büchi reaction) of 2,3-dihydrofuran-3-ol derivatives 1 with benzophenone.

  在2,3-二氢呋喃-3的光化学[2 + 2]环加成反应（Paternò–Büchi反应）中，报道了立体选择性，反式构型的氧杂环丁烷2与顺式构型的氧杂环丁烷2的显着温度效应（非线性艾林图）-ol衍生物1与二苯甲酮。
• Stereochemical control in the ester enolate Claisen rearrangement. 2. Chairlike vs boatlike transition-state selection
  作者：Robert E. Ireland、Peter Wipf、Jia Ning Xiang

  DOI：10.1021/jo00011a023

  日期：1991.5

  The preference for chair- and boatlike transition-state geometries in the ester enolate Claisen rearrangement of straight chain, carbocyclic, and heterocyclic propanoates was investigated. A novel stereoelectronic effect in pyranoid and furanoid glycal systems leads to a significant relative stabilization of the boatlike vs the chairlike TS double-ended-dagger. The preferred transition state in six- and five-membered carbocyclic systems is highly dependent on steric factors, as the energy difference between chair- and boatlike TS double-ended-dagger tends to be small. With straight-chain substrates, a significant contribution of the boatlike TS double-ended-dagger to the rearrangement product mixture is only expected in bis-donor substituted allylic esters.