7-chloro-7-phenyl-2-oxabicyclo<3.2.0>heptan-6-one | 143308-01-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 7-chloro-7-phenyl-2-oxabicyclo<3.2.0>heptan-6-one
• 英文别名: (1S,5R,7R)-7-chloro-7-phenyl-2-oxabicyclo[3.2.0]heptan-6-one
• CAS: 143308-01-4
• 化学式: C₁₂H₁₁ClO₂
• 分子量: 222.671
• InChiKey: HXPVAVMQAWQHJK-DLOVCJGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-chloro-7-phenyl-2-oxabicyclo<3.2.0>heptan-6-one 以 甲醇 、 苯 为溶剂， 反应 7.67h， 生成 2-phenyl-4-methoxy-3-hexen-6-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
• 作为产物：
  描述：

  2,3-二氢呋喃 、 DL-2-氯-2-苯基乙酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以75%的产率得到7-chloro-7-phenyl-2-oxabicyclo<3.2.0>heptan-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.