8β-phenyl-2,7-dioxabicyclo<3.3.0>octan-6-one | 143308-07-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 8β-phenyl-2,7-dioxabicyclo<3.3.0>octan-6-one
• 英文别名: (3aR,6R,6aS)-6-phenyl-3,3a,6,6a-tetrahydro-2H-furo[3,4-b]furan-4-one
• CAS: 143308-07-0；143392-89-6
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: UQJMGCHRTYJHGP-MXWKQRLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 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 hydroxide 作用下， 以 乙腈 为溶剂， 反应 7.0h， 以40%的产率得到8β-phenyl-2,7-dioxabicyclo<3.3.0>octan-6-one
  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.