4-((2-chlorophenyl)ethynyl)-N,N-dimethylaniline | 1445990-50-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-((2-chlorophenyl)ethynyl)-N,N-dimethylaniline
• 英文别名: 4-[2-(2-chlorophenyl)ethynyl]-N,N-dimethylaniline
• CAS: 1445990-50-0
• 化学式: C₁₆H₁₄ClN
• 分子量: 255.747
• InChiKey: INOUEKQTMWVXDO-UHFFFAOYSA-N

物化性质

• 沸点：
  394.0±27.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-((2-chlorophenyl)ethynyl)-N,N-dimethylaniline 、 二苯基乙炔 在 三叔丁基膦 、 palladium diacetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 cesium pivalate 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以74%的产率得到N,N-dimethyl-4-(10-phenylindeno[2,1-a]inden-5-yl)aniline
  参考文献：
  名称：

  Pd-Catalyzed Cascade Crossover Annulation of o-Alkynylarylhalides and Diarylacetylenes Leading to Dibenzo[a,e]pentalenes

  摘要：

  A novel and selective Pd-catalyzed cascade crossover-annulation of o-alkynylarylhalides and diarylacetylenes for the synthesis of dibenzo[a,e]pentalenes has been reported. Various arylacetylenes with a wide range of functional groups were tolerated, producing the corresponding multisubstituted dibenzopentalenes with the different substituents on the aromatic rings in good to high yields under the optimized reaction conditions. The reaction proceeds through a Pd-catalyzed cascade carbopalladation and C-H activation. The use of the combined DBU and CsOPiv bases is crucial for the successful implementation of the present cross-annulation.

  DOI：

  10.1021/ja403382d
• 作为产物：
  描述：

  1-氯-2-碘苯 、 4-二甲基氨基苯乙炔 在 copper(l) iodide 、 四(三苯基膦)钯 、 N,N-二异丙基乙胺 作用下， 以 水 为溶剂， 以56%的产率得到4-((2-chlorophenyl)ethynyl)-N,N-dimethylaniline
  参考文献：
  名称：

  Halogenated diarylacetylenes repress c-myc expression in cancer cells

  摘要：

  Halogenated diarylacetylenes that possess fluorine or chlorine substituents in one aryl ring and N-methylamino or N,N-dimethylamino in the other aryl ring inhibit the proliferation of LS174T colon cancer cells through the repression of c-myc expression and induction of the cyclin-dependent kinase inhibitor-1 (i.e., p21(Wif1/Cip1)) and represent potentially useful antineoplastic agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.04.113

文献信息

• HALOGENATED DIARYLACETYLENES AND METHODS OF TREATING CANCER
  申请人：UNIVERSITY OF KENTUCKY RESEARCH FOUNDATION

  公开号：US20150272908A1

  公开（公告）日：2015-10-01

  Halogenated diarylacetylenes, e.g., diarylacetylenes having at least one halo substituent in one aryl ring and an amine in the opposing aryl ring, can inhibit the proliferation of LS174T colon cancer cells through the inhibition of c-myc and induction of the cyclin-dependent kinase inhibitor-1 (i.e., p21(Wif1/Cip1)). Such compounds are useful as antineoplastic agents.

  卤代二芳基乙炔，例如，在一个芳基环中至少有一个卤素取代物，在另一个芳基环中有一种胺基，可以通过抑制c-myc并诱导细胞周期依赖性激酶抑制剂-1（即p21（Wif1 / Cip1））来抑制LS174T结肠癌细胞的增殖。这些化合物可用作抗肿瘤剂。
• US9895324B2
  申请人：——

  公开号：US9895324B2

  公开（公告）日：2018-02-20