4-fluoro-N-(3-phenylallylidene)aniline | 3382-76-1

• 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: 4-fluoro-N-(3-phenylallylidene)aniline
• 英文别名: 1-(4-fluorophenyl)-4-phenyl-1-azabuta-1,3-diene；cinnamal-4-fluoroaniline；Cinnamyliden-p-fluoranilin；1-(p-fluorophenyl)-4-phenyl-1-azabutadiene；N-(4-fluorophenyl)-3-phenylprop-2-en-1-imine
• CAS: 3382-76-1
• 化学式: C₁₅H₁₂FN
• 分子量: 225.265
• InChiKey: OPKYZHOEFJCYAD-UHFFFAOYSA-N

物化性质

• 沸点：
  357.4±42.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  3
• 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

安全信息

• 海关编码：
  2925290090

反应信息

• 作为反应物：
  描述：

  4-fluoro-N-(3-phenylallylidene)aniline 在 potassium carbonate 、 三乙胺 、 对甲苯磺酰氯 、 三苯基膦 作用下， 以 甲醇 、 氯仿 、 丙酮 为溶剂， 生成
  参考文献：
  名称：

  β-Lactam-synthon-interceded diastereoselective synthesis of novel thioxo-imidazolines: a convenient access to functionally decorated 4,5-dihydro-imidazoles

  摘要：

  The manuscript describes a facile synthesis of an equimolar diastereomeric mixture of 2-thioxo-imidazolines via beta-lactam synthon approach using racemic N-aryl beta-lactams. The diastereoselectivity in the reaction has been introduced by initially synthesizing 3-isothiocyanato-beta-lactams with methoxide assisted amidolysis and intramolecular cyclization. The synthesized diastereoselective trans-2-thioxo-imidazolines were easily converted into diversely functionalized 4,5-dihydro-imidazoles through usual synthetic transformations without the aid of any protic or Lewis acid conditions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.089
• 作为产物：
  描述：

  苯甲醛 在 magnesium sulfate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 17.0h， 生成 4-fluoro-N-(3-phenylallylidene)aniline
  参考文献：
  名称：

  α，β-不饱和醛的甲硅烷基化还原胺化反应：合成β-甲硅烷基化仲胺的简便方法

  摘要：

  这里描述的是路易斯酸性硼烷催化剂介导的α，β-不饱和醛的还原胺化/氢化硅烷化级联。本反应系统提供了一种单罐合成路线，可通往其他先前催化无法达到的β-甲硅烷基化仲胺。对亚胺的甲硅烷基化还原进行的比较1 H NMR研究表明，伯胺反应物的空间体积极大地影响了催化效率和区域选择性。该策略适用于广泛的底物，并适用于一锅克级合成。此外，还发现非对映选择性地引入β-甲硅烷基是可行的（dr高达71:29）。

  DOI：

  10.1002/chem.201800958

文献信息

• Development of Chiral Spiro Phosphoramidites for Rhodium‐Catalyzed Enantioselective Reactions
  作者：Zhiyao Zheng、Yuxi Cao、Dongsheng Zhu、Zheng Wang、Kuiling Ding

  DOI：10.1002/chem.201900486

  日期：2019.7.17

  monophosphoramidite ligands 6 a–m were synthesized, which demonstrated excellent enantioselectivity in RhI‐catalyzed asymmetric hydrogenation of a dehydro amino acid methyl ester. Ligands 6 a–m were also successfully applied in the RhI‐catalyzed enantioselective [4+2] cycloaddition of α,β‐unsaturated imines with isocyanates, which afforded the corresponding pyrimidinones in good yields (60–92 %) with high enantioselectivities

  合成了一系列带有2,2'-二甲基，环戊基或环己基稠合环的1,1'-螺代双茚满-7,7'-二醇（SPINOL）类似物，并通过X阐明了它们的独特结构特征射线晶体学。在这些支架的基础上，合成了手性单亚磷酰胺配体6 a – m，在Rh I催化的脱氢氨基酸甲酯的不对称氢化反应中表现出优异的对映选择性。配体6 a – m也成功应用于Rh Iα，β-不饱和亚胺与异氰酸酯的催化对映选择性[4 + 2]环加成反应，可提供相对应的嘧啶酮，收率高（60-92％），对映选择性高（75-92％ee）。
• Synthesis of β-Phosphinolactams from Phosphenes and Imines
  作者：Xingyang Fu、Xinyao Li、Jiaxi Xu

  DOI：10.1021/acs.orglett.1c03182

  日期：2021.11.19

  Various cis-β-phosphinolactams are synthesized stereoselectively for the first time from imines and diazo(aryl)methyl(diaryl)phosphine oxides under microwave irradiation. Diazo(aryl)methyl(diaryl)phosphine oxides first undergo the Wolf rearrangement to generate phosphenes. Imines nucleophilically attack the phosphenes followed by an intramolecular nucleophilic addition via less steric transition states

  在微波辐射下，首次从亚胺和重氮（芳基）甲基（二芳基）氧化膦立体选择性地合成了各种顺式-β-膦内酰胺。重氮（芳基）甲基（二芳基）氧化膦首先经历沃尔夫重排以生成膦。亚胺亲核攻击膦，然后通过较少的空间过渡态进行分子内亲核加成，得到最终的顺式-β-膦内酰胺。C-苯乙烯亚胺通常以比C-芳基亚胺更高的产率产生 β-膦内酰胺。通过 DFT 理论计算对立体选择性和提出的机制进行了合理化。
• Azide–alkynecycloadditionen route towards 1H-1,2,3-triazole-tethered β-lactam–ferrocene and β-lactam–ferrocenylchalcone conjugates: synthesis and in vitro anti-tubercular evaluation
  作者：Kewal Kumar、Séverine Carrère-Kremer、Laurent Kremer、Yann Guérardel、Christophe Biot、Vipan Kumar

  DOI：10.1039/c2dt32148c

  日期：——

  A diverse range of triazoles were prepared following well established, Cu-mediated azide–alkyne cycloaddition reactions with the aim of probing the anti-tubercular structure–activity relationships (SAR) within the β-lactam–ferrocene–triazole conjugate family. The anti-tubercular evaluation studies of the synthesized conjugates revealed that none of the scaffolds exhibited any activity that restricted mycobacterial growth even at high doses. The introduction of various substituents onto the N-1 of the β-lactam ring, introducing mono- or di-ferrocenylchalcone substituents at the C-3 position as well as introducing a spacer of varying chain length failed to produce any significant enhancement in the activity profiles. The described protocol was a successful attempt on the inclusion of a ferrocene nucleus in the β-lactam family tethered via triazole linkers having metabolic stability and physicochemical favourability.

  通过铜催化的叠氮化物-炔烃环加成反应，合成了一系列多样化的三唑化合物，旨在探索β-内酰胺-二茂铁-三唑缀合物家族中的抗结核结构-活性关系（SAR）。对合成缀合物的抗结核评估研究表明，即使在较高剂量下，这些骨架均未显示出任何抑制分枝杆菌生长的活性。将各种取代基引入β-内酰胺环的N-1位，在C-3位引入单或双二茂铁查尔酮取代基，以及引入不同链长的间隔基，均未能显著增强活性。所描述的方案成功尝试了通过具有代谢稳定性和物化优势的三唑连接子将二茂铁核纳入β-内酰胺家族。
• An Ecofriendly and Efficient Approach through Sodium Oxalate Catalyst for the Synthesis of Azomethines and α-Aminonitriles Ligands Employing Aqueous Medium
  作者：Bikramjit Singh、Jatinder Singh Aulakh、Baldev Singh

  DOI：10.14233/ajchem.2022.23715

  日期：——

  An ecofriendly, efficient, inorganic salt catalyzed facile method has been developed for the synthesis of potential ligands azomethines and α-aminonitriles employing aqueous medium. This procedure involves the use of Zn(CN)2 an inexpensive, less toxic as compared to KCN, ecofriendly and readily available effective cyanide source. Cyanated products specially have been isolated in high yield on usual

  开发了一种环保、高效、无机盐催化的简便方法，用于使用水介质合成潜在配体偶氮甲碱和α-氨基腈。该过程涉及使用 Zn(CN)2，与 KCN 相比，Zn(CN)2 是一种廉价、毒性较小、环保且易于获得的有效氰化物源。特别是，氰化产物已通过常规后处理程序以高产率分离出来。在甲醇和 DMF 溶剂中，评估了所有产生的化合物对某些细菌和真菌菌株的体外抗菌活性。在测试的化合物中，b和g对枯草芽孢杆菌具有最有希望的抗菌作用。此外，发现化合物a和c是对抗白色念珠菌最有效的抗真菌剂。
• β-Lactam-Synthon-Interceded Synthesis of Isatin-Imidazolidine-2-thione Conjugates with Structural Validation using Molecular Dynamic Simulations and Cytotoxic Evaluation
  作者：Vipan Kumar、Parvesh Singh、Denver Hendricks、Krishna Bisetty

  DOI：10.1055/s-0033-1339315

  日期：——

  beta-Lactam-synthon-interceded synthesis of isatin-imidazolidine-2-thione conjugates was carried out via base-assisted intermolecular amidolysis of 3-isothiocyanato-2-azetidinones with C-5 substituted isatins. The observed enolization in the assigned structure of the conjugates was validated using molecular dynamic (MD) simulations performed under explicit solvent conditions. The synthesized scaffolds were also evaluated for their cytotoxic profiles against the oesophageal cancer cell line WHCO1.