2,5-dimethylene-2,5-dihydro-furan | 13314-90-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2,5-dimethylene-2,5-dihydro-furan
• 英文别名: 2,5-Dimethylene-furan；2,5-dimethylidenefuran
• CAS: 13314-90-4
• 化学式: C₆H₆O
• 分子量: 94.113
• InChiKey: ZTFYRZFWGRCCCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  Vinyl-p-xylylen 、 2,5-dimethylene-2,5-dihydro-furan 以12%的产率得到
  参考文献：
  名称：

  HAMMOND P. S.; LONGONE D. T., TETRAHEDRON LETT. , 1978, NO 5, 415-418

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(chloromethyl)-5-methylfuran 600.0 ℃ 、2.67 Pa 条件下， 生成 2,5-dimethylene-2,5-dihydro-furan
  参考文献：
  名称：

  Detection of 2,5-dimethylene-2,5-dihydrothiophene and thiophenoradialene

  摘要：

  DOI：

  10.1016/s0040-4039(00)82314-x

文献信息

• Oligomerization of the Thiophene-Based <i>p</i>-Quinodimethanes 2,5-Dimethylene-2,5-dihydrothiophene and 2-Ethylidene-5-methylene-2,5-dihydrothiophene
  作者：Walter S. Trahanovsky、Deborah Louise Miller、Yili Wang

  DOI：10.1021/jo961528i

  日期：1997.12.1

  Flash vacuum pyrolysis (FVP) of (5-methyl-2-thiophene-yl)methyl benzoate (8) produces in ca. 75% yield 2,5-dimethylene-2,3-dihydrothiophene, S-monomer (3). S-Monomer 3 is relatively stable dissolved in carbon disulfide-chloroform at -78 degrees C. The structure of 3 is confirmed by its spectral properties. When a 0.17 M solution of S-monomer 3 was allowed to warm to room temperature, SS-dimer 5 ([2,2](2,5)thiophenophane, 14.7%), SSS-trimer 7 ([2,2,2](2,5)thiophenophane, 44.3%), and polymer were produced. A small amount (<1%) of an SSSS-tetramer was detected by GC/MS. The mechanism proposed for the formation of these oligomers involves the combination of two molecules of 3 to give an intermediate diradical (11) that can close to form dimer 5 or react with additional molecules of 3 to form the higher oligomers. Evidence for the trapping of diradical 11 by 2,5-dimethylene-2,5-dihydrofuran (O-monomer 2) was obtained. Co-oligomerization of S-monomer 3 and O-monomer 2 gave four compounds containing the thiophene moiety: OS-dimer 16, SS-dimer 5, OSS-trimer 17, and SSS-trimer 7. Some OO-dimer 4 was produced but no 000-trimer 6 was observed and only a trace of OOS-trimer 18 was detected. Additional support for the diradical mechanism was obtained from the study of the oligomerization of the methyl derivatives of 3,2-ethylidene-5-methylene-2,5-dihydrothiophene (10, E and Z isomers), prepared by the FVP of (5-ethyl-2-thiophene-yl)methyl benzoate (9). Oligomerization of 10 gave several dimers and trimers including two acyclic dimers that are accounted for by intramolecular disproportionation.
• NELSON, DAVID A.;HALLEN, RICHARD T., J. ANAL. AND APPL. PYROL., 12,(1987) N 1, 11-17
  作者：NELSON, DAVID A.、HALLEN, RICHARD T.

  DOI：——

  日期：——