2-phenacyl-2-buten-4-olide | 143308-12-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-phenacyl-2-buten-4-olide
• 英文别名: 4-phenacyl-2H-furan-5-one
• CAS: 143308-12-7
• 化学式: C₁₂H₁₀O₃
• 分子量: 202.21
• InChiKey: KSFOWKHUOUHONG-UHFFFAOYSA-N

物化性质

• 沸点：
  413.6±28.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  7-chloro-7-phenyl-2-oxabicyclo<3.2.0>heptan-6-one 在 sodium azide 、 lithium perchlorate 作用下， 以 丙酮 为溶剂， 反应 10.0h， 以25%的产率得到2-<1'-(4'-phenyl-2'-triazolyl)-2'-phenylethyl>-2-azidobutan-4-olide
  参考文献：
  名称：

  Synthetic methods. 39. Reactions and rearrangements in 2-oxa[3.2.0]bicycloheptanones

  摘要：

  The furan-fused chlorocyclobutanone 6 undergoes reaction with O, N, S, C nucleophiles at a much slower rate than its pyran homolog, which is attributed to a reluctance to enolization. Instead of substitution products, rearranged products were formed. For instance, 7-membered ring lactones 8 and 9 were derived via vinyl ketenes, while 5-membered ring lactones 12, 19, and 20 resulted from opening of the cyclobutanone and/or of the tetrahydrofuran ring. Phenylthiolate behaved exceptionally as a nucleophile, leading, presumably via electron transfer, to ipso substitution and then to a naphthofuran.

  DOI：

  10.1021/jo00045a020

文献信息

• Synthetic methods. 39. Reactions and rearrangements in 2-oxa[3.2.0]bicycloheptanones
  作者：Simha Naidorf-Meir、Alfred Hassner

  DOI：10.1021/jo00045a020

  日期：1992.9

  The furan-fused chlorocyclobutanone 6 undergoes reaction with O, N, S, C nucleophiles at a much slower rate than its pyran homolog, which is attributed to a reluctance to enolization. Instead of substitution products, rearranged products were formed. For instance, 7-membered ring lactones 8 and 9 were derived via vinyl ketenes, while 5-membered ring lactones 12, 19, and 20 resulted from opening of the cyclobutanone and/or of the tetrahydrofuran ring. Phenylthiolate behaved exceptionally as a nucleophile, leading, presumably via electron transfer, to ipso substitution and then to a naphthofuran.