5-(8,9,10,11-Tetrahydro-8-oxobenzonaphtho<1,2-d>furan-11a(7aH)-yl)-2-pentenoic Acid Ethyl Ester | 135525-38-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(8,9,10,11-Tetrahydro-8-oxobenzonaphtho<1,2-d>furan-11a(7aH)-yl)-2-pentenoic Acid Ethyl Ester
• 英文别名: ethyl (E)-5-[(7aR,11aR)-8-oxo-7a,9,10,11-tetrahydronaphtho[2,1-b][1]benzofuran-11a-yl]pent-2-enoate
• CAS: 135525-38-1
• 化学式: C₂₃H₂₄O₄
• 分子量: 364.441
• InChiKey: HAZHPTQOHVCEKH-FCYCGOIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (E)-5-<2-(2-Naphthalenyloxy)-3-oxo-1-cyclohexen-1-yl>-2-pentenoic Acid Ethyl Ester 以 甲醇 、 甲苯 为溶剂， 反应 5.0h， 以45%的产率得到8,9,10,11-Tetrahydro-8-oxo-7a,11a-propanobenzonaphtho<1,2-d>furan-14-acetic Acid Ethyl Ester
  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

文献信息

• Tandem photocyclization-intramolecular addition reactions of aryl vinyl sulfides. Observation of a novel [2 + 2] cycloaddition-allylic sulfide rearrangement
  作者：James P. Dittami、Xiao Yi Nie、Hong Nie、H. Ramanathan、C. Buntel、S. Rigatti、Jon Bordner、Debra L. Decosta、Paul Williard

  DOI：10.1021/jo00030a022

  日期：1992.2

  Photocyclization of aryl vinyl sulfides reportedly proceeds via thiocarbonyl ylide intermediates. The photochemical behavior of several aryl vinyl sulfides, which incorporate a pendant alkene side chain, was explored. In general, naphthyl and phenyl vinyl thioethers provided products which are consistent with photocyclization to a thiocarbonyl ylide intermediate followed by either intramolecular hydrogen shift or subsequent intramolecular ylide-alkene addition. Product distribution is influenced by solvent and temperature effects. Novel secondary photoprocesses were also observed during some reactions. Thus, irradiation of naphthyl vinyl sulfide 20 gave dihydrothiophene 22 which underwent subsequent intramolecular [2 + 2] cycloaddition to provide 24. Upon prolonged irradiation 24 undergoes a novel allylic sulfide rearrangement to provide 25.