3-(3-Butenyl)-2-(2-naphthalenylthio)-2-cyclohexen-1-one | 121851-32-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-(3-Butenyl)-2-(2-naphthalenylthio)-2-cyclohexen-1-one
• 英文别名: 3-(But-3-en-1-yl)-2-[(naphthalen-2-yl)sulfanyl]cyclohex-2-en-1-one；3-but-3-enyl-2-naphthalen-2-ylsulfanylcyclohex-2-en-1-one
• CAS: 121851-32-9
• 化学式: C₂₀H₂₀OS
• 分子量: 308.444
• InChiKey: GPHLZSXQCSZUJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(3-Butenyl)-2-(2-naphthalenylthio)-2-cyclohexen-1-one 以 甲苯 为溶剂， 反应 3.5h， 以79%的产率得到
  参考文献：
  名称：

  杂原子定向光芳基化过程中的分子内加成反应

  摘要：

  研究了在杂原子指导的光芳基化反应中产生的光瞬态物质的分子内加成反应。对于光环化反应和分子内加成反应均观察到新的温度效应。此外，观察到的加成产物与分子间加成至光瞬态物质时获得的（3 + 2）环加合物有很大不同。

  DOI：

  10.1016/s0040-4039(01)80616-x
• 作为产物：
  描述：

  3-乙氧基-2-环己烯-1-酮 在 sodium hydroxide 、 双氧水 、 potassium hydride 、 magnesium 作用下， 以 甲醇 为溶剂， 反应 26.58h， 生成 3-(3-Butenyl)-2-(2-naphthalenylthio)-2-cyclohexen-1-one
  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

• Intramolecular addition reactions during heteroatom directed photoarylation
  作者：James P. Dittami、H. Ramanathan、S. Breining

  DOI：10.1016/s0040-4039(01)80616-x

  日期：1989.1

  The intramolecular addition reactions of phototransient species generated upon heteroatom directed photoarylation were investigated. Novel temperature effects were observed for both the photocyclization and intramolecular addition reactions. Moreover, the addition products observed differ considerably from the (3 + 2) cycloadducts which were obtained upon intermolecular addition to the phototransient

  研究了在杂原子指导的光芳基化反应中产生的光瞬态物质的分子内加成反应。对于光环化反应和分子内加成反应均观察到新的温度效应。此外，观察到的加成产物与分子间加成至光瞬态物质时获得的（3 + 2）环加合物有很大不同。
• DITTAMI, JAMES P.;RAMANATHAN, H.;BREINING, S., TETRAHEDRON LETT., 30,(1989) N, C. 795-798
  作者：DITTAMI, JAMES P.、RAMANATHAN, H.、BREINING, S.

  DOI：——

  日期：——
• DITTAMI, JAMES P.;NIE, XIAO-YI;BUNTEL, CHRISTOPHER J.;RIGATTI, STEVEN, TETRAHEDRON. LETT., 31,(1990) N7, C. 3821-3824
  作者：DITTAMI, JAMES P.、NIE, XIAO-YI、BUNTEL, CHRISTOPHER J.、RIGATTI, STEVEN

  DOI：——

  日期：——
• 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.
• Dittami, James P.; Nie, Xiao Yi, Synthetic Communications, 1990, vol. 20, # 4, p. 541 - 547
  作者：Dittami, James P.、Nie, Xiao Yi

  DOI：——

  日期：——