(Z)-2-(4-bromophenyl)-3-(4-methoxyphenyl) acrylonitrile | 133132-70-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (Z)-2-(4-bromophenyl)-3-(4-methoxyphenyl) acrylonitrile
• 英文别名: (z)-2-(4-Bromophenyl)-3-(4-methoxyphenyl)acrylonitrile；(Z)-2-(4-bromophenyl)-3-(4-methoxyphenyl)prop-2-enenitrile
• CAS: 133132-70-4
• 化学式: C₁₆H₁₂BrNO
• 分子量: 314.181
• InChiKey: CRCZMXPHIXPEHL-GXDHUFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-2-(4-bromophenyl)-3-(4-methoxyphenyl) acrylonitrile 、 二苯胺 在 三叔丁基膦 、 palladium diacetate 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以84.5%的产率得到(Z)-2-(4-(diphenylamino)phenyl)-3-(4-methoxyphenyl)-acrylonitrile
  参考文献：
  名称：

  Mechanochromic and thermochromic fluorescent properties of cyanostilbene derivatives

  摘要：

  Two isomers (TPA-CNa and TPA-CNb) consisting of twisted triphenylamine and cyanostilbene were synthetized by Knoevenagel condensation and C-N coupling reaction. The fluorescent colours of two isomers in crystalline state were sky-blue for TPA-CNa and green for TPA-CNb with quantum yields (Phi(f)) of 44.9% and 7.7%, respectively. The single crystal X-ray diffractometry revealed the fully different molecular conformations and packing modes of TPA-CNa (planar) and TPA-CNb (twisting), which might be the reason for different Phi(f). The reversible mechanochromic and thermochromic fluorescence switching was observed in crystalline TPA-CNa powders. The sky-blue crystals were changed into the green-emissive solids after grinding, and they recovered their original state upon heating at 60 degrees C over 2 min. The reversible conversion of fluorescence colour was also realized by a pure thermal process. Powder X-ray diffractometry clearly demonstrated that the mechanochromic and thermochromic behaviour could be attributed to the crystal-to-amorphisation phase transition. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.03.017
• 作为产物：
  描述：

  对溴苯乙腈 、 4-甲氧基苯甲醛 生成 (Z)-2-(4-bromophenyl)-3-(4-methoxyphenyl) acrylonitrile
  参考文献：
  名称：

  Heating and mechanical force-induced “turn on” fluorescence of cyanostilbene derivative with H-type stacking

  摘要：

  研究人员获得了一种具有聚集诱导发光特性的氰芪基衍生物，它在外部刺激下表现出多种发光强度。制备的所需染料晶体显示出相当微弱的荧光。加热后，其荧光可以开启，量子产率为 13.3%。熔化和凝固粉末的量子产率进一步提高到 28.6%。应用粉末 X 射线衍射仪、荧光光谱、荧光寿命实验和单晶 XRD 分析研究了分子堆积模式的变化。这种荧光 "暗""亮 "的转变很容易用肉眼分辨，与相变有关。具有 H 型填料和多种可变相互作用的平面氰二苯乙烯可能是多种发光强度特性的关键因素。

  DOI：

  10.1039/c3ce41221k

文献信息

• Direct C-S Bond Functionalization of Benzyl Mercaptan
  作者：Khokan Choudhuri、Milan Pramanik、Prasenjit Mal

  DOI：10.1002/ejoc.202000521

  日期：2020.7.7

  Using 1,10‐phenanthroline as organocatalyst and t BuOK as base, cascaded activation of three different bonds: C(sp3)–H, benzylic C–S, and aryl–halide could be achievable in one pot.

  以1,10-菲咯啉为有机催化剂，以t BuOK为碱，可以在一锅中实现三个不同键的级联活化：C（sp 3）–H，苄基C–S和芳基–卤化物。
• Buu-Hoi; Xuong, Bulletin de la Societe Chimique de France, 1957, p. 650,652
  作者：Buu-Hoi、Xuong

  DOI：——

  日期：——
• Frost, Justus Liebigs Annalen der Chemie, 1889, vol. 250, p. 162
  作者：Frost

  DOI：——

  日期：——
• Long, Huan-Yuan; Zhang, Jin; Li, Zi-Wei, Journal of the Chemical Society of Pakistan, 2019, vol. 41, # 5, p. 868 - 873
  作者：Long, Huan-Yuan、Zhang, Jin、Li, Zi-Wei、Zhou, Peng、Peng, Tian-Ying、He, Guo-Wen

  DOI：——

  日期：——
• Mechanochromic and thermochromic fluorescent properties of cyanostilbene derivatives
  作者：Yujian Zhang、Guilin Zhuang、Mi Ouyang、Bin Hu、Qingbao Song、Jingwei Sun、Cheng Zhang、Cheng Gu、Yuanxiang Xu、Yuguang Ma

  DOI：10.1016/j.dyepig.2013.03.017

  日期：2013.9

  Two isomers (TPA-CNa and TPA-CNb) consisting of twisted triphenylamine and cyanostilbene were synthetized by Knoevenagel condensation and C-N coupling reaction. The fluorescent colours of two isomers in crystalline state were sky-blue for TPA-CNa and green for TPA-CNb with quantum yields (Phi(f)) of 44.9% and 7.7%, respectively. The single crystal X-ray diffractometry revealed the fully different molecular conformations and packing modes of TPA-CNa (planar) and TPA-CNb (twisting), which might be the reason for different Phi(f). The reversible mechanochromic and thermochromic fluorescence switching was observed in crystalline TPA-CNa powders. The sky-blue crystals were changed into the green-emissive solids after grinding, and they recovered their original state upon heating at 60 degrees C over 2 min. The reversible conversion of fluorescence colour was also realized by a pure thermal process. Powder X-ray diffractometry clearly demonstrated that the mechanochromic and thermochromic behaviour could be attributed to the crystal-to-amorphisation phase transition. (C) 2013 Elsevier Ltd. All rights reserved.