2-(4-methoxyphenyl)-2,4,6-cycloheptatrienone | 40394-02-3

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: 2-(4-methoxyphenyl)-2,4,6-cycloheptatrienone
• 英文别名: 2-(4-methoxyphenyl)tropone；2-(p-methoxyphenyl)tropone；2-(4-methoxy-phenyl)-cycloheptatrienone；2-(4-Methoxy-phenyl)-cycloheptatrienon；2-(4-methoxy-phenyl)-2,4,6-cycloheptatrienone；2-(4-Methoxyphenyl)cyclohepta-2,4,6-trien-1-one
• CAS: 40394-02-3
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: NTNCJCQMAQWMPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  2-(4-methoxyphenyl)-2,4,6-cycloheptatrienone 在 氢氧化钾 作用下， 生成 2-联苯-(4-甲氧基)羧酸
  参考文献：
  名称：

  Nozoe et al., Sci. Rep. Tohoku Univ., Ser. 1: Phys., Chem., Astron., 1954, vol. 38, p. 141,142

  摘要：

  DOI：
• 作为产物：
  描述：

  环庚三烯酚酮甲苯磺酸盐 、 三丁基(4-甲氧基苯基)锡 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 2,6-二叔丁基-4-甲基苯酚 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 以67%的产率得到2-(4-methoxyphenyl)-2,4,6-cycloheptatrienone
  参考文献：
  名称：

  Regio- and Diastereoselective Stepwise [8 + 3]-Cycloaddition Reaction between Tropone Derivatives and Donor–Acceptor Cyclopropanes

  摘要：

  A novel SnCl4-catalyzed [8 + 3]-cycloaddition reaction between tropone derivatives and donor-acceptor aminocyclopropanes Is described. The process leads to the formation of amino-substituted tetrahydrocyclohepta[b]pyrans with complete regio- and diastereoselectivity. Density functional theory calculations suggest that the cycloaddition occurs stepwise through an aromatic zwitterionic intermediate.

  DOI：

  10.1021/ol4020656

文献信息

• Unique Condensation Reactions of Tropones with Bis(benzoylthio)trithiafulvene Leading to 10a<i>H</i>-Cyclohepta[<i>c</i>]-1,3-dithiolo[<i>e</i>][1,2]dithiin-2-thione
  作者：Katsuhiro Saito、Kazuaki Ito、Chizuko Kabuto、Kensuke Takahashi

  DOI：10.1246/bcsj.64.2383

  日期：1991.8

  Reactions of tropone derivatives with 4,5-bis(benzoylthio)-1,3-dithiole-2-thione (2,3,6-trithiafulvene derivative) afforded 1,3,5-cycloheptatriene derivatives doubly substituted by trithiafulvene and S–S groups (10aH-cyclohepta[c]-1,3-dithiolo[e][1,2]dithiin-2-thione). The structure of the 1,3,5-cycloheptatriene derivative and its crystal structure were investigated by single crystal X-ray analysis to show the existence of a unique three-dimensional network of the molecules through S···S contacts.

  与4,5-双(苯甲酰硫)-1,3-二硫噻唑-2-硫酮（2,3,6-三硫富烯衍生物）反应的脱氢莰烯衍生物得到双重取代的1,3,5-环庚三烯衍生物，取代基为三硫富烯和S–S基团（10aH-环庚[c]-1,3-二硫噻唑[e][1,2]二硫烯-2-硫酮）。通过单晶X射线分析对1,3,5-环庚三烯衍生物的结构及其晶体结构进行了研究，显示了通过S···S接触存在独特的三维分子网络。
• Diels–Alder Reaction of Tropones with Arynes: Synthesis of Functionalized Benzobicyclo[3.2.2]nonatrienones
  作者：Manikandan Thangaraj、Sachin Suresh Bhojgude、Rajesh H. Bisht、Rajesh G. Gonnade、Akkattu T. Biju

  DOI：10.1021/jo500819w

  日期：2014.5.16

  A new procedure for the mild, practical, and scalable Diels–Alder reaction of tropones with arynes is reported. Differently substituted tropones undergo selective [4 + 2] cycloaddition with arynes generated in situ by the fluoride-induced 1,2-elimination of 2-(trimethylsilyl)aryl triflates, allowing the formation of functionalized benzobicyclo[3.2.2]nonatrienone derivatives in moderate to good yields

  据报道，一种新的程序可以使托克酮与芳烃发生温和，实用和可扩展的狄尔斯-阿尔德反应。通过氟诱导的2-（三甲基甲硅烷基）芳基三氟甲磺酸酯的1,2-消除，原位生成的芳烃经历不同取代的对苯二酚的选择性[4 + 2]环加成反应，从而适度形成官能化的苯并双环[3.2.2]壬三烯酮衍生物高产。此外，还介绍了环加合物的光物理性质。
• Stereoselective(2.PI.+4.PI.)-Type Addition Reactions of Benzocyclobutadiene with 2-Substituted Tropones and 8,8-Dicyanoheptafulvene.
  作者：Katsuhiro SAITO、Hiroyuki WATANABE、Kensuke TAKAHASHI

  DOI：10.1248/cpb.40.2831

  日期：——

  Thermal addition reactions of 2-substituted tropones and 8, 8-dicyanoheptafulvene with benzocyclobutadiene proceeded stereoselectively to produce endo-[2π+4π]-type cyclo adducts, where the troponoid compounds acted as 4π components. Molecular orbital calculations were employed to explain the selectivity.

  2-取代的特罗庞和8,8-二氰基七氟烯与苯环丁二烯的热加成反应以立体选择性进行，生成内端-[2π+4π]型环加成物，其中特罗庞类化合物作为4π成分。采用分子轨道计算来解释选择性。
• Palladium-catalyzed carbonylative coupling of aryl triflates with organostannanes
  作者：Antonio M. Echavarren、J. K. Stille

  DOI：10.1021/ja00213a032

  日期：1988.3
• The reaction of troponoid with ylide VI A novel synthesis of unsymmetric biphenyl
  作者：Yukio Sugimura、Kimio Iino、Isao Kawamoto、Yukichi Kishida

  DOI：10.1016/s0040-4039(01)85149-2

  日期：1972.1