3-fluoro-N-(4-methylbenzylidene)aniline | 1363406-41-0

• 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: 3-fluoro-N-(4-methylbenzylidene)aniline
• 英文别名: N-(3-fluorophenyl)-1-(4-methylphenyl)methanimine
• CAS: 1363406-41-0
• 化学式: C₁₄H₁₂FN
• 分子量: 213.254
• InChiKey: LSGHNQGXTPQOBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  3-fluoro-N-(4-methylbenzylidene)aniline 、 苯乙炔 、 3-methoxy-N-(4-methylbenzylidene)aniline 在 三氟甲磺酸 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以10%的产率得到2-p-tolyl-4-phenyl-7-fluoroquinoline
  参考文献：
  名称：

  Silver-Mediated C–H Activation: Oxidative Coupling/Cyclization of N-Arylimines and Alkynes for the Synthesis of Quinolines

  摘要：

  A silver-mediated tandem protocol for the synthesis of quinolines involving the oxidative coupling/cyclization of N-arylimines and alkynes has been developed. We demonstrated that scenario-dependent metalation could occur either at the ortho C-H bond of an N-arylimine through protonation-driven enhancement of acidity or at the terminal C-H bond of an alkyne by virtue of the carbophilic pi-acidity of silver. The diverse set of mechanistic manifolds implemented with a single type of experimental protocol points toward the importance of stringent reactivity analysis of each individual potentially reactive molecular site. Importantly, the direct arene C H bond activation provides a unique and distinct mechanistic handle for the expansion of reactivity paradigms for silver. As expected, the protocol allows for the incorporation of both internal and terminal alkynes into the products, and in addition, both electron-withdrawing and -donating groups are tolerated on N-arylimines, thus enabling the vast expansion of substituent architectures on quinoline framework. Further, an intriguing phenomenon of structural isomerization and chemical bond cleavage has been observed for aliphatic internal alkynes.

  DOI：

  10.1021/jo202087j
• 作为产物：
  描述：

  3-氟苯胺 、 对甲基苯甲醛 以 neat (no solvent) 为溶剂， 反应 0.25h， 生成 3-fluoro-N-(4-methylbenzylidene)aniline
  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

• 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
• An attempt of molecular design and synthesis of 3,4′/4,3′-disubstituted benzylideneanilines with specified UV-Vis absorption maximum wavelength
  作者：Linyan Wang、Chaotun Cao、Chenzhong Cao

  DOI：10.1002/poc.3341

  日期：2014.10

  Thirty‐one samples of 3,4′/4,3′‐disubstituted benzylideneanilines (XBAY) with specified UV–Vis absorption maximum wavelength (λmax) were designed and synthesized by applying the equation (Eqn 1) which was abstracted from the UV–Vis absorption maximum wavelength energy (νmax = 1/λmax) of 4,4′‐disubstituted benzylideneanilines. Then, the UV–Vis data (λmax) of the designed compounds were measured in anhydrous

  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.
• Silver-Mediated C–H Activation: Oxidative Coupling/Cyclization of <i>N</i>-Arylimines and Alkynes for the Synthesis of Quinolines
  作者：Xu Zhang、Baoqing Liu、Xin Shu、Yang Gao、Haipeng Lv、Jin Zhu

  DOI：10.1021/jo202087j

  日期：2012.1.6

  A silver-mediated tandem protocol for the synthesis of quinolines involving the oxidative coupling/cyclization of N-arylimines and alkynes has been developed. We demonstrated that scenario-dependent metalation could occur either at the ortho C-H bond of an N-arylimine through protonation-driven enhancement of acidity or at the terminal C-H bond of an alkyne by virtue of the carbophilic pi-acidity of silver. The diverse set of mechanistic manifolds implemented with a single type of experimental protocol points toward the importance of stringent reactivity analysis of each individual potentially reactive molecular site. Importantly, the direct arene C H bond activation provides a unique and distinct mechanistic handle for the expansion of reactivity paradigms for silver. As expected, the protocol allows for the incorporation of both internal and terminal alkynes into the products, and in addition, both electron-withdrawing and -donating groups are tolerated on N-arylimines, thus enabling the vast expansion of substituent architectures on quinoline framework. Further, an intriguing phenomenon of structural isomerization and chemical bond cleavage has been observed for aliphatic internal alkynes.
• 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。