1,1,2,2-Tetracyano-3-(p-methoxyphenyl)cyclobutane | 61715-62-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,1,2,2-Tetracyano-3-(p-methoxyphenyl)cyclobutane
• 英文别名: 1,1,2,2-tetracyano-3-p-anisylcyclobutane；3-(p-Methoxyphenyl)-1,1,2,2-tetracyanocyclobutan；1.1.2.2-Tetracyano-3-(p-anisyl)-cyclobutan；1.1.2.2-Tetracyano-3-(p-methoxy-phenyl)-cyclobutan；3-(4-Methoxyphenyl)cyclobutane-1,1,2,2-tetracarbonitrile
• CAS: 61715-62-6
• 化学式: C₁₅H₁₀N₄O
• 分子量: 262.271
• InChiKey: WXNGOAQQICNJFF-UHFFFAOYSA-N

物化性质

• 熔点：
  182-183 °C
• 沸点：
  597.6±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,1,2,2-Tetracyano-3-(p-methoxyphenyl)cyclobutane 以 甲醇 为溶剂， 生成 1,1,2-Tricyano-4-(p-methoxy-phenyl)-1,3-butadien
  参考文献：
  名称：

  Cyanocarbon Chemistry. XX.^1,2 1,2,2-Tricyano-1,3-butadienes

  摘要：

  DOI：

  10.1021/ja00870a038
• 作为产物：
  描述：

  4-甲氧基苯乙烯 、 四氰基乙烯 以 甲苯 为溶剂， 反应 72.0h， 以21%的产率得到1,1,2,2-Tetracyano-3-(p-methoxyphenyl)cyclobutane
  参考文献：
  名称：

  某些乙烯基和乙炔基[2.2]对环环烷与一些亲二烯体的新环加成反应

  摘要：

  4-乙烯基[2.2]对环环烯（），4,12-，（），4,15-，（）和4,16-二乙烯基[2.2]对环环烯（）以及4-乙烯基-[2.2]对环环烯（）与四氰基乙烯（TCNE）进行[2 + 2]环加成反应。这些反应涉及形成电荷转移复合物作为初始步骤。含2,3-二氯-5,6-二氰基苯并醌（DDQ），溴苯腈（BRL）以及4-苯基-1,2,4-三唑啉-3,5-二酮和4-乙烯基[2.2]对环环烷（）作为二烯，发生了[2 + 4]环加成反应。4,12-，（），4,15-，（）和4,16-之间的反应受二环电子相互作用的影响。

  DOI：

  10.1016/s0040-4020(01)87210-0

文献信息

• Synthesis and crystal structure of the metallacyclopentane complex 2,2,5,5-tetracyano-3-ethoxy-1,1-bis(triphenylphosphine)-1-platinacyclopentane
  作者：Renzo Ros、Maurizio Lenarda、Nevenka Bresciani Pahor、Mario Calligaris、Paolo Delise、Lucio Randaccio、Mauro Graziani

  DOI：10.1039/dt9760001937

  日期：——

  Reaction of [Pt(PPh3)2(C2H4)] with 1,1,2,2-tetracyano-3-ethoxycyclobutane and 1,1,2,2-tetracyano-3-(p-methoxyphenyl)cyclobutane gives the platinum-cyclopentane complexes (1)[Pt(PPh3)2C4H3(CN)4OEt}] and (2)[Pt(PPh3)2C4H3(CN)4C6H4OMe}]. The crystal structure of (1) was determined from diffractometer data. Crystals are monoclinic, space group P21/c with cell parameters a= 10.586(6), b= 20.422(10), c=

  [Pt（PPh 3）2（C 2 H 4）]与1,1,2,2-四氰基-3-乙氧基环丁烷和1,1,2,2-四氰基-3-（对甲氧基苯基）环丁烷的反应产生铂-环戊烷络合物（1）[Pt（PPh 3）2 C 4 H 3（CN）4 OEt}]和（2）[Pt（PPh 3）2 C 4 H 3（CN）4 C 6 H 4 OMe}]。由衍射仪数据确定（1）的晶体结构。晶体是单斜晶体，空间群P 2 1 /c单元参数为a = 10.586（6），b = 20.422（10），c = 23.234（10）Å，β= 115.23（10）°。用重原子法求解结构，最后的最小二乘法精化得到2 636次反射的R 0.092。铂原子已插入碳-碳键中。比较了三元和四元摩托车。
• Influence of Lewis Acids on the Cycloaddition Reactions of Cyano- and Carbomethoxy-Substituted Olefins
  作者：Warunee Srisiri、Anne Buyle Padias、H. K. Hall

  DOI：10.1021/jo00097a054

  日期：1994.9

  The reactions of electrophilic olefins substituted with cyano and/or carbomethoxy groups with donor olefins are investigated. The donor olefins include, in order of decreasing donor character, phenyl vinyl sulfide, isobutyl vinyl ether, tert-butyldimethylsilyl vinyl ether, p-methoxy- and p-methylstyrene, and styrene. The reactions vary ii om [2 + 2] cycloadditions to Diels-Alder reactions to spontaneous free radical copolymerizations. The course of the reaction is determined by both the electron disparity between the two reacting olefins and by the substitution pattern on the electrophilic olefin. Lewis acids (ZnCl2 or ethereal LiClO4) are added to form complexes with the acceptor olefins, resulting in a larger electron disparity between the reactants. With the highly electrophilic olefins with gem-dicyano groups, such as tetracyanoethylene, dimethyl 1,1-dicyanoethylene-2,2-dicarboxylate, and methyl beta,beta-dicyanoacrylate, [2 + 2] cycloadditions occur at room temperature, except for the reaction of TCNE with styrene which has to be carried out in 5 M ethereal LiClO4. With olefins containing one cyano and one carbomethoxy group on the same carbon, dimethyl dicyanofumarate and dimethyl cyanofumarate, inverse electron demand Diels-Alder cycloaddition involving the ester substituent dominates in reactions with the most nucleophilic olefins. The [2 + 2] cycloadducts can be obtained in the presence of Lewis acid. With olefins with two carbomethoxy-substituents on the same carbon, dimethyl 2-cyanoethene-1,1-dicarboxylate and trimethyl ethylenetricarboxylate, the reactions are much slower, and [2 + 4] cycloaddition dominates with the most reactive donor olefins, while the [2 + 2] cycloadduct can be obtained in the presence of Lewis acid. With several acceptor olefins, free radical copolymerizations compete with the cycloadditions when reacted with the least reactive donor olefins. The reaction tendencies are discussed in light of the electron disparity between the olefins. The influence of the Lewis acid on the conformational equilibria and on the reaction course is also addressed.
• <b>Cyanocarbon Chemistry. XIX.^1,2 Tetracyanocyclobutanes from Tetracyanoethylene and Electron-rich Alkenes</b>
  作者：J. K. Williams、D. W. Wiley、B. C. McKusick

  DOI：10.1021/ja00870a037

  日期：1962.6