N-(3-bromobenzylidene)-4-fluoroaniline | 1841-48-1

• 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: N-(3-bromobenzylidene)-4-fluoroaniline
• 英文别名: N-[(3-Bromophenyl)methylene]-4-fluorobenzenamine；1-(3-bromophenyl)-N-(4-fluorophenyl)methanimine
• CAS: 1841-48-1
• 化学式: C₁₃H₉BrFN
• 分子量: 278.124
• InChiKey: VEZKWRIWVWSWED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 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：
  12.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(3-bromobenzylidene)-4-fluoroaniline 在 甲醇 、 sodium tetrahydroborate 作用下， 生成 N-[(3-bromophenyl)methyl]-4-fluoroaniline
  参考文献：
  名称：

  Synthesis of N-benzyl-N-phenylthiophene-2-carboxamide analogues as a novel class of enterovirus 71 inhibitors

  摘要：

  一系列N-苄基-N-苯基噻吩-2-羧酰胺类似物被确定为新型人类肠道病毒71抑制剂，EC50值高达1.42μM。

  DOI：

  10.1039/c5ra07286g
• 作为产物：
  描述：

  间溴苯甲醛 、 4-氟苯胺 以 neat (no solvent) 为溶剂， 反应 0.25h， 生成 N-(3-bromobenzylidene)-4-fluoroaniline
  参考文献：
  名称：

  具有指定UV-Vis吸收最大波长的3,4'/ 4,3'-二取代的亚苄基苯胺的分子设计和合成尝试

  摘要：

  使用从紫外线中提取的方程式（方程1）设计并合成了31个具有指定的UV-Vis吸收最大波长（λmax）的3,4'/ 4,3'-二取代的亚苄基苯胺（XBAY）样品–4,4'-二取代的亚苄基苯胺的最大吸收波长能量（νmax  = 1 / λmax）。然后，在无水乙醇中测量设计化合物的UV-Vis数据（λmax）。设计化合物的预测UV-Vis数据与实验数据一致，其中平均绝对误差为2.9 nm。结果表明，方程1可用于预测UV-Vis吸收λmax4,4'-二取代的亚苄基苯胺和3,4'/ 4,3'-二取代的亚苄基苯胺的总值。对于同一对基团（X和Y），至少可以得到四种具有不同λmax值的二取代的亚苄基苯胺化合物。它可能提供了一种方便的方法来设计用于亚苄基苯胺化合物的光学材料。版权所有©2014 John Wiley＆Sons，Ltd.

  DOI：

  10.1002/poc.3341

文献信息

• Povarov Reaction of Cycloiminium Formed in Situ via Hydroamination Cycloisomerization of Homopropargylic Amines with Electron-Rich Olefins
  作者：Qiangqiang Liu、Chan Wang、Qiang Li、Yajie Hou、Ye Wu、Lingyan Liu、Weixing Chang、Jing Li

  DOI：10.1021/acs.joc.6b02496

  日期：2017.1.20

  A new, one-pot cascade reaction of homopropargylic amines with electron-rich olefins is developed in the presence of Cu(OTf)2 and affords a series of octahydrofuro[3,2-c]pyrrolo[1,2-a]quinoline derivatives in yields of 38–80%. This reaction proceeds through an intramolecular hydroamination cyclization of homopropargylic amine to generate a highly reactive cycloenamine intermediate in situ that subsequently

  在Cu（OTf）2存在下开发了一种新的单炔胺与富电子烯烃的级联反应，并提供了一系列八氢呋喃[3,2- c ]吡咯并[1,2- a ]喹啉衍生物收率为38–80％。该反应通过高炔丙基胺的分子内加氢胺化反应进行，以生成高反应性的环烯胺中间体，该中间体随后异构化成环亚胺阳离子，然后与二氢呋喃，二氢吡喃或二氢吡咯进行Povarov型反应。值得注意的是，Al 2 O 3添加剂在有效抑制高炔丙基胺竞争性二聚方面起着关键作用。
• Substituent effects on the stretching vibration of C═N in multi‐substituted benzylideneanilines
  作者：Linyan Wang、Chaotun Cao、Chenzhong Cao

  DOI：10.1002/poc.3969

  日期：2019.9

  synthesized, and their infrared absorption spectra were recorded in this paper. On the basis of the stretching vibration frequencies νC═N of C═N bridging bond of 158 samples of substituted XBAYs (including 57 samples of 4,4′‐disubstituted XBAYs from reference and 101 samples of substituted XBAYs synthesized in this paper), an extensional research of substituent effects on the νC═N values from 4,4′‐disubstituted

  合成了39个3,4'/ 4,3'/ 3,3'-二取代的亚苄基苯胺（XBAYs）样品和52个多取代的XBAYs样品，并记录了它们的红外吸收光谱。根据158个取代的XBAY样品（包括参考文献中的57个4,4'-双取代的XBAY样品和101个合成的取代的XBAY样品）的C═N桥键的拉伸振动频率νC═N，进行了取代基对从4,4'-双取代XBAY到多取代XBAYs的νC═N值的扩展研究。用于量化νC═N的修正方程获得了多取代XBAY的值（如公式（3）所示）。公式（3）表明，对于多取代XBAYs的νC═N值进行定量回归分析，不能忽略Y的激发态取代基常数以及X和X之间的取代基特定的交叉相互作用效应。与等式（1）相比，等式（3）在量化替代XBAY的νC═N值方面具有更广泛的应用和更高的准确性。
• The Diverse Reactivity of Homopropargylic Amines as “Masked” 1C Synthons for the Aza-Friedel-Crafts Alkylation of Indoles
  作者：Hao Chen、Min Ni、Xiaofeng Bao、Chan Wang、Lingyan Liu、Weixing Chang、Jing Li

  DOI：10.1002/ejoc.201701523

  日期：2018.1.31

  A novel type of “masked” 1C synthon was developed through the hydroamination cyclization‐protonation of homopropargylic amines to act as aza‐Friedel–Crafts alkylation reagents to react with indoles. A variety of 3‐(2‐pyrrolidinyl)indoles were generated in good to high yields.

  新型的“掩蔽” 1C合成子是通过加氢胺化丙炔基胺的质子化作用来充当氮杂-Friedel-Crafts烷基化试剂与吲哚反应的。产生了各种3-（2-吡咯烷基）吲哚，产率高到高。
• Comparison of the substituent effects on the¹³C NMR with the¹H NMR chemical shifts of CHN in substituted benzylideneanilines
  作者：Linyan Wang、Chaotun Cao、Chenzhong Cao

  DOI：10.1002/mrc.4248

  日期：2015.7

  Fifty-two samples of substituted benzylideneanilines XPhCH=NPhYs (XBAYs) were synthesized, and their NMR spectra were determined in this paper. Together with the NMR data of other 77 samples of XBAYs quoted from literatures, the (1) H NMR chemical shifts (deltaH (CH=N)) and (13) C NMR chemical shifts (deltaC (CH=N)) of the CH=N bridging group were investigated for total of 129 samples of XBAYs. The

  合成了52个取代的亚苄基苯胺XPhCH = NPhYs（XBAYs）样品，并确定了其NMR光谱。连同文献中引用的其他77个XBAY样品的NMR数据一起，CH的（1）H NMR化学位移（deltaH（CH = N））和（13）C NMR化学位移（deltaC（CH = N）） = N桥接组共研究了129个XBAY样本。结果表明deltaH（CH = N）和deltaC（CH = N）没有明显的线性关系，这与理论上认为deltaH（CH = N）值将随着deltaC（CH = N）增大的理论思想相反。 ）值增加。通过深入的分析，我们发现X / Y组的sigmaF和sigmaR对deltaH（CH = N）和deltaC（CH = N）的影响是相反的。X和Y（Deltasigma（2））之间的取代基特定交叉相互作用对deltaH（CH = N）和deltaC（CH = N）的影响是不同的; 分别在deltaH（CH
• Design and Optimization of Novel Hydroxamate-Based Histone Deacetylase Inhibitors of Bis-Substituted Aromatic Amides Bearing Potent Activities against Tumor Growth and Metastasis
  作者：Feifei Yang、Tao Zhang、Haigang Wu、Yang Yang、Ning Liu、Ang Chen、Qiang Li、Jingjie Li、Liwen Qin、Beier Jiang、Xin Wang、Xiufeng Pang、Zhengfang Yi、Mingyao Liu、Yihua Chen

  DOI：10.1021/jm5012148

  日期：2014.11.26

  Histone deacetylases (HDACs) are one of the most promising drug targets for cancer therapy, and since more than 90% of all cancer-related deaths are associated with tumor metastasis, developing strategies to inhibit tumor metastasis while retaining anti-tumor growth activity are of great interest. Herein we demonstrated the design and identification of a series of novel hydroxamate-based HDAC inhibitors bearing potent activities against tumor growth and metastasis. Optimization of the initial hit resulted in the discovery of new HDAC inhibitors through studying the structureactivity relationship. Among them, compound 11b, one of the most potent leads, exhibited nanomolar IC50 values toward inhibition of class I and IIb HDACs as well as sub-micromolar activity against proliferation and migration of breast cancer cells in vitro. More importantly, it also significantly suppressed tumor growth in a breast tumor xenograft mouse model and dose-dependently blocked in vivo tumor metastasis in a mouse pulmonary metastasis model.