1,2,3,4-Tetrahydro-4-oxo-4a,9b-propanodibenzothiophene-12-acetic acid, ethyl ester | 138874-81-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: 1,2,3,4-Tetrahydro-4-oxo-4a,9b-propanodibenzothiophene-12-acetic acid, ethyl ester
• 英文别名: ethyl 2-(10-oxo-8-thiatetracyclo[7.4.3.01,9.02,7]hexadeca-2,4,6-trien-16-yl)acetate
• CAS: 138874-81-4
• 化学式: C₁₉H₂₂O₃S
• 分子量: 330.448
• InChiKey: WZDWEQGIYCNVQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(Phenylthio)-3-oxo-1-cyclohexene-1-propanal 在 sodium hydride 、 二甲基亚砜 作用下， 以 甲苯 为溶剂， 反应 4.08h， 生成 1,2,3,4-Tetrahydro-4-oxo-4a,9b-propanodibenzothiophene-12-acetic acid, ethyl ester
  参考文献：
  名称：

  Tandem photocyclization-intramolecular addition reactions of aryl vinyl sulfides. Observation of a novel [2 + 2] cycloaddition-allylic sulfide rearrangement

  摘要：

  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.

  DOI：

  10.1021/jo00030a022

文献信息

• Photoinitiated intramolecular ylide-alkene cycloaddition reactions
  作者：James P. Dittami、Nie Xiao-Yi、Christopher J. Buntel、Steven Rigatti

  DOI：10.1016/s0040-4039(00)97478-1

  日期：1990.1

  The intramolecular olefin addition reactions of phototransient species were investigated. Photolysis of aryl vinyl sulfides which incorporate the ethyl butenoate functional group provide ene-like products and or (3+2) adducts. Product formation is governed by both structural features and reaction conditions.

  研究了光瞬态物质的分子内烯烃加成反应。掺入丁烯酸乙酯官能团的芳基乙烯基硫醚的光解提供了类似烯的产物和/或（3 + 2）加合物。产物的形成受结构特征和反应条件的支配。
• Intramolecular addition reactions of carbonyl ylides formed during photocyclization of aryl vinyl ethers
  作者：James P. Dittami、Xiao Yi Nie、Hong Nie、H. Ramanathan、Scott Breining、Jon Bordner、Debra L. Decosta、Jeffrey Kiplinger、Philip Reiche、Richard Ware

  DOI：10.1021/jo00019a020

  日期：1991.9

  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.