ethyl (1R,3S,8S,12S)-4-oxo-2-oxahexacyclo[9.9.1.01,12.03,8.08,12.013,18]henicosa-13,15,17,19-tetraene-21-carboxylate | 135525-39-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (1R,3S,8S,12S)-4-oxo-2-oxahexacyclo[9.9.1.01,12.03,8.08,12.013,18]henicosa-13,15,17,19-tetraene-21-carboxylate
• CAS: 135525-39-2
• 化学式: C₂₃H₂₄O₄
• 分子量: 364.441
• InChiKey: DGHQLPDNLGFGJM-JZMDZJMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-(8,9,10,11-Tetrahydro-8-oxobenzonaphtho<1,2-d>furan-11a(7aH)-yl)-2-pentenoic Acid Ethyl Ester 反应 4.5h， 生成 ethyl (1R,3S,8S,12S)-4-oxo-2-oxahexacyclo[9.9.1.01,12.03,8.08,12.013,18]henicosa-13,15,17,19-tetraene-21-carboxylate
  参考文献：
  名称：

  Intramolecular addition reactions of carbonyl ylides formed during photocyclization of aryl vinyl ethers

  摘要：

  Photocyclization of aryl vinyl ethers reportedly proceeds via carbonyl ylide intermediates. The photochemical behavior of several aryl vinyl ethers, which incorporate a pendant alkene side chain, was explored. Naphthyl vinyl ethers 1c and 1d provided products that are consistent with photocyclization and subsequent intramolecular ylide-alkene addition. Product distribution is influenced by solvent and temperature effects. Thus, irradiation of 1c in toluene provides 9a in 87% yield. However, irradiation of 1c in methanol/toluene (1:1) provides 3c (45%), 11 (24%), and 12 (23%). Product 12 results from photoinitiated intramolecular [2 + 2] cycloaddition of the butenoate ester side chain to the naphthalene system.

  DOI：

  10.1021/jo00019a020