2-Cyan-3,3-bis-(4-methoxy-phenyl)-acrylonitril | 21453-19-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Cyan-3,3-bis-(4-methoxy-phenyl)-acrylonitril
• 英文别名: 2-(Bis(4-methoxyphenyl)methylene)malononitrile；2-[bis(4-methoxyphenyl)methylidene]propanedinitrile
• CAS: 21453-19-0
• 化学式: C₁₈H₁₄N₂O₂
• 分子量: 290.321
• InChiKey: OIGOUJJCCHQOQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-Cyan-3,3-bis-(4-methoxy-phenyl)-acrylonitril 在 samarium diiodide 、 2,2,2-三氟乙醇 作用下， 以 四氢呋喃 为溶剂， 生成 2-[Bis(4-methoxyphenyl)methyl]propanedinitrile
  参考文献：
  名称：

  使用SmI2进行还原：用于区分质子转移的两种操作模式的机械探针。

  摘要：

  在四个质子供体：H（2）O，MeOH，i-PrOH和三氟乙醇（TFE）的存在下，研究了在THF中用SmI（2）还原1,1-二芳基-2,2-二氰基乙烯的方法。在质子供体浓度低的情况下，前两个动力学顺序几乎一致，在高浓度时，动力学顺序接近四个，而对于i-PrOH和TFE，对数-对数图是线性的，斜率小于1。详细的分析显示，诸如H（2）O和MeOH的对数对数曲线表示通过与可变数量的质子供体络合的自由基阴离子和Sm（+3）的离子对内的质子化作用，表明了主要贡献分子，而线性图是从本体溶液质子化的结果。

  DOI：

  10.1039/b713014g
• 作为产物：
  描述：

  4,4'-二甲氧基二苯甲酮 、 丙二腈 在 乙酸铵 作用下， 以 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 2-Cyan-3,3-bis-(4-methoxy-phenyl)-acrylonitril
  参考文献：
  名称：

  Mass spectra of dicyanomethylene derivatives of benzophenone analogs

  摘要：

  AbstractThe dicyanomethylene derivative of a benzophenone analog significantly alters the fragmentation pattern observed during electron impact ionization of the underivatized parent compound. A double bond connecting the dicyanomethylene moiety to the parent compound is cleaved during a major fragmentation pathway for many of these compounds. A mechanism involving rearrangement of two hydrogen atoms is proposed to rationalize cleavage of this double bond. Conventional mass spectra as well as collisionally activated dissociation mass spectra of selected ions of several model compounds are reported and described in support of a proposed fragmentation mechanism.

  DOI：

  10.1002/oms.1210181102

文献信息

• Meerwein Arylation of Aryl(alkyl)idenemalononitriles and Diazonium Salts for the Synthesis of 2-(Aryl(alkyl)/arylmethylene)malononitrile Derivatives
  作者：Xiaoqing Lv、Shengjun Liu、Yu Guo、Lijiu Gao、Liming Zhao、Jinpeng Zhang、Liangce Rong

  DOI：10.1021/acs.joc.3c01161

  日期：2023.9.1

  arylation reaction from aryl(alkyl)idenemalononitriles and diazonium salts for the synthesis of 2-(aryl(alkyl)/arylmethylene)malononitrile derivatives under mild conditions was well developed. Different from the general addition reactions between alkenes and diazonium salts, this study performed the traditional coupling reaction for the formation of C(sp2)–C(sp2) bond arylation products. The radical reaction

  在温和条件下，由芳基（烷基）亚甲基丙二腈和重氮盐合成2-（芳基（烷基）/芳基亚甲基）丙二腈衍生物的无金属Meerwein芳基化反应得到了很好的发展。与一般的烯烃与重氮盐之间的加成反应不同，本研究进行了传统的偶联反应，形成C(sp 2 )–C(sp 2 )键芳基化产物。自由基反应机理在对照实验中得到了很好的验证。该方法的其他优点是底物范围广和良好的群体耐受性。此外，所得产物可以很容易地转化为高价值的不对称酮和加氢反应。
• Abdou, Sadek; Fahmy, Sherif Mahmoud; Sadek, Kamal Usef, Heterocycles, 1981, vol. 16, # 12, p. 2177 - 2180
  作者：Abdou, Sadek、Fahmy, Sherif Mahmoud、Sadek, Kamal Usef、Elnagdi, Mohamed Hilmy

  DOI：——

  日期：——
• ABDOU, SADEK;FAHMY, SHERIF, MAHMOUD;SADEK, KAMAL, USEF;ELNAGDI, MOHAMED, +, HETEROCYCLES, 1981, 16, N 12, 2177-2180
  作者：ABDOU, SADEK、FAHMY, SHERIF, MAHMOUD、SADEK, KAMAL, USEF、ELNAGDI, MOHAMED, +

  DOI：——

  日期：——
• Mass spectra of dicyanomethylene derivatives of benzophenone analogs
  作者：Ching-Bore Wang、Guor-Rong Her、J. Throck Watson

  DOI：10.1002/oms.1210181102

  日期：1983.11

  AbstractThe dicyanomethylene derivative of a benzophenone analog significantly alters the fragmentation pattern observed during electron impact ionization of the underivatized parent compound. A double bond connecting the dicyanomethylene moiety to the parent compound is cleaved during a major fragmentation pathway for many of these compounds. A mechanism involving rearrangement of two hydrogen atoms is proposed to rationalize cleavage of this double bond. Conventional mass spectra as well as collisionally activated dissociation mass spectra of selected ions of several model compounds are reported and described in support of a proposed fragmentation mechanism.
• Reductions with SmI2: mechanistic probe for distinguishing between two operational modes of proton transfer
  作者：Alexander Tarnopolsky、Shmaryahu Hoz

  DOI：10.1039/b713014g

  日期：——

  is linear with a slope smaller than one. Detailed analysis shows that a curved log-log plot such as for H(2)O and MeOH is indicative of a major contribution by protonation within an ion pair of the radical anion and Sm(+3) complexed to a variable number of proton donor molecules, whereas a linear plot is a result of protonation from the bulk solution.

  在四个质子供体：H（2）O，MeOH，i-PrOH和三氟乙醇（TFE）的存在下，研究了在THF中用SmI（2）还原1,1-二芳基-2,2-二氰基乙烯的方法。在质子供体浓度低的情况下，前两个动力学顺序几乎一致，在高浓度时，动力学顺序接近四个，而对于i-PrOH和TFE，对数-对数图是线性的，斜率小于1。详细的分析显示，诸如H（2）O和MeOH的对数对数曲线表示通过与可变数量的质子供体络合的自由基阴离子和Sm（+3）的离子对内的质子化作用，表明了主要贡献分子，而线性图是从本体溶液质子化的结果。