2,3-Dihydrooxepin | 3422-09-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环化合物
• 英文名称: 2,3-Dihydrooxepin
• 英文别名: 2,3-dihydro-oxepine；2,3-Dihydro-oxepin；2.3-Dihydro-oxepin；Dihydrooxepin；2,3-dihydrooxepine
• CAS: 3422-09-1
• 化学式: C₆H₈O
• 分子量: 96.1289
• InChiKey: WLGQUBABAPAJNB-UHFFFAOYSA-N

物化性质

• 沸点：
  118-120 °C
• 密度：
  0.944±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2,3-Dihydrooxepin 、 6-lithio-3,4-dihydro-2H-pyran 以 四氢呋喃 为溶剂， 生成 1-lithio-1-oxa-heptatriene
  参考文献：
  名称：

  Investigation into the mechanism of lithiation of 2,3-dihydrooxepin

  摘要：

  The NMR characterization of the trienolate product of lithiation of 2,3-dihydrooxepin with 6-lithiodihydropyran in THF is reported. The NMR spectra also support a direct ring opening upon allylic lithiation via an E2-type mechanism rather than vinylic lithiation or stepwise allylic lithiation. We also found the structure of the trienolate product of this reaction to be the Z, Z configuration. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.07.048
• 作为产物：
  描述：

  anti-2-Oxatricyclo<4.1.0.0^3,5>heptan 生成 2,3-Dihydrooxepin
  参考文献：
  名称：

  Golz, Thomas; Hammes, Susann; Klaerner, Frank-Gerrit, Chemische Berichte, 1993, vol. 126, # 2, p. 485 - 498

  摘要：

  DOI：

文献信息

• Allylic vs. vinylic deprotonation reactions of cyclic vinyl ethers. 7-Lithio-2,3,4,5-tetrahydrooxepin: synthesis and carbon-13 NMR spectrum
  作者：Fred T. Oakes、Fu An Yang、John F. Sebastian

  DOI：10.1021/jo00137a013

  日期：1982.7
• Golz Thomas, Hammes Susann, Klaerner Frank-Gerrit, Chem. Ber., 126 (1993) N 2, S 485-498
  作者：Golz Thomas, Hammes Susann, Klaerner Frank-Gerrit

  DOI：——

  日期：——
• OAKES, F. T.;YANG, FU-AN;SEBASTIAN, J. F., J. ORG. CHEM., 1982, 47, N 16, 3094-3097
  作者：OAKES, F. T.、YANG, FU-AN、SEBASTIAN, J. F.

  DOI：——

  日期：——
• Golz, Thomas; Hammes, Susann; Klaerner, Frank-Gerrit, Chemische Berichte, 1993, vol. 126, # 2, p. 485 - 498
  作者：Golz, Thomas、Hammes, Susann、Klaerner, Frank-Gerrit

  DOI：——

  日期：——
• Investigation into the mechanism of lithiation of 2,3-dihydrooxepin
  作者：Zhiqing Yan、John F. Sebastian

  DOI：10.1016/j.tetlet.2004.07.048

  日期：2004.8

  The NMR characterization of the trienolate product of lithiation of 2,3-dihydrooxepin with 6-lithiodihydropyran in THF is reported. The NMR spectra also support a direct ring opening upon allylic lithiation via an E2-type mechanism rather than vinylic lithiation or stepwise allylic lithiation. We also found the structure of the trienolate product of this reaction to be the Z, Z configuration. (C) 2004 Elsevier Ltd. All rights reserved.

表征谱图