dicyanomethylene-4-chlorobenzophenone | 15517-61-0

• 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: dicyanomethylene-4-chlorobenzophenone
• 英文别名: 3-<4-Chlor-phenyl>-2-cyan-3-phenyl-acrylonitril；1,1-Dicyan-2-phenyl-2-(4-chlor-phenyl)-aethylen；3-(4-Chlor-phenyl)-2-cyan-3-phenyl-acrylonitril；Propanedinitrile, [(4-chlorophenyl)phenylmethylene]-；2-[(4-chlorophenyl)-phenylmethylidene]propanedinitrile
• CAS: 15517-61-0
• 化学式: C₁₆H₉ClN₂
• 分子量: 264.714
• InChiKey: UAOKDQHQPPEJDS-UHFFFAOYSA-N

物化性质

• 沸点：
  395.2±37.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  间溴苯甲腈 、 dicyanomethylene-4-chlorobenzophenone 在 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以89%的产率得到2-(3-bromophenyl)-3-phenyl-3-(4-chlorophenyl)-4-cyano-5-amino-3H-pyrrole
  参考文献：
  名称：

  Convenient preparations of polysubstituted 3H-pyrroles promoted by SmI2

  摘要：

  已研究了在铈(II)碘化物的诱导下，1,1-二芳基-2,2-二氰基乙烯或1,1-二芳基-2-氰基-2-乙氧基羧乙烯与芳香族腈的分子间还原偶联反应。在中性且温和的条件下，制备了产率良好至优异的多取代3H-吡咯。

  DOI：

  10.1039/b102268g
• 作为产物：
  描述：

  4-氯二苯甲酮 、 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 dicyanomethylene-4-chlorobenzophenone
  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

• Transformation of<i>gem</i>-Dicyanoethenes by Samarium: Direct Formation of Indenes or Direct Decyanation with in Situ Disilylation
  作者：Yongjun Liu、Fuqiang Zhang、Yan Qi、Yongmin Zhang、Shusheng Zhang

  DOI：10.1002/ejoc.200800258

  日期：2008.11

  Intramolecular cyclization of 1,1-diaryl-2,2-dicyanoethenes promoted by samarium metal in DMF in the presence of TMSCl allowed direct construction of the indene core, whereas 1-alkyl-1-aryl-2,2-dicyanoethenes underwent intermolecular coupling cyclization and decyanation under the same conditions. Simultaneously, disilylation occurred at the amino moiety resulting from the reduction of the cyano group

  在 TMSCl 存在下，由钐金属在 DMF 中促进的 1,1-二芳基-2,2-二氰乙烯分子内环化允许直接构建茚核，而 1-烷基-1-芳基-2,2-二氰乙烯进行分子间偶联在相同条件下进行环化和脱氰。同时，由于氰基还原，氨基部分发生二甲硅烷基化。然而，当存在微量水时，仅观察到 C=C 键的简单还原。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008）
• SYNTHESIS OF 3H-PYRROLES PROMOTED BY SAMARIUM/CAT. IODINE SYSTEM
  作者：Xiaoliang Xu、Yongmin Zhang

  DOI：10.1081/scc-120006027

  日期：2002.1

  The intermolecular reductive coupling of 1,1-diaryl-2,2-dicyanoethylenes or 1,1-diaryl-2-cyano-2-ethoxycarbonylethylenes with aromatic nitriles induced by samarium and catalytic iodine was studied. 3H-Pyrroles were prepared in moderate to good yields under neutral and mild conditions.
• 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.
• Convenient preparations of polysubstituted 3H-pyrroles promoted by SmI2
  作者：Xiaoliang Xu、Yongmin Zhang

  DOI：10.1039/b102268g

  日期：2001.11.1

  The intermolecular reductive coupling of 1,1-diaryl-2,2-dicyanoethylenes or 1,1-diaryl-2-cyano-2-ethoxycarbonylethylenes with aromatic nitriles induced by samarium(II) iodide has been studied. Polysubstituted 3H-pyrroles were prepared in good to excellent yields under neutral and mild conditions.

  已研究了在铈(II)碘化物的诱导下，1,1-二芳基-2,2-二氰基乙烯或1,1-二芳基-2-氰基-2-乙氧基羧乙烯与芳香族腈的分子间还原偶联反应。在中性且温和的条件下，制备了产率良好至优异的多取代3H-吡咯。