3-chloro-N-(1-phenylethylidene)aniline | 81512-13-2

• 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-chloro-N-(1-phenylethylidene)aniline
• 英文别名: m-Chloro-N-(α-methyl benzylidene) aniline；m-Chloro-N-(alpha-methyl benzylidene) aniline；N-(3-chlorophenyl)-1-phenylethanimine
• CAS: 81512-13-2
• 化学式: C₁₄H₁₂ClN
• 分子量: 229.709
• InChiKey: KICQGFIBESUFTC-UHFFFAOYSA-N

物化性质

• 沸点：
  325.3±34.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 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：
  1

反应信息

• 作为反应物：
  描述：

  3-chloro-N-(1-phenylethylidene)aniline 在 lithium aluminium tetrahydride 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 N-α-phenylethyl-m-chloroaniline
  参考文献：
  名称：

  Zirconium complexes stabilized by amine-bridged bis(phenolato) ligands as precatalysts for intermolecular hydroamination reactions

  摘要：

  由胺桥联的双(酚ato)配体稳定的五配位锆配合物 5 和 7 比六配位的配合物 1–4 在催化分子间氢氨化反应时更为活跃。

  DOI：

  10.1039/c5dt02643a
• 作为产物：
  描述：

  2-hydroxy-2-phenylpropionitrile 在 氢氧化钾 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 0.75h， 生成 3-chloro-N-(1-phenylethylidene)aniline
  参考文献：
  名称：

  Shukla; Astik; Thaker, Journal of the Indian Chemical Society, 1981, vol. 58, # 12, p. 1182 - 1182

  摘要：

  DOI：

文献信息

• Simple, efficient and reusable Pd–NHC catalysts for hydroamination
  作者：Qian Chen、Lanlan Lv、Meng Yu、Yanhui Shi、Yuling Li、Guangsheng Pang、Changsheng Cao

  DOI：10.1039/c3ra42990c

  日期：——

  series of chelating NHC–palladium complexes with different alkane-bridges of the type Pd[NHC–(CH2)n–NHC]X2 (X = Br or Cl, n = 2–4) were synthesized, where NHC is a triazolyl-N-heterocyclic carbene donor ligand. The bromide complexes with n = 2 and 3 were characterized by X-ray crystallography. The effects of the length of the bridge and halide ligand on the catalytic reactivity in the hydroamination reaction

  合成了一系列具有不同Pd [NHC–（CH 2）n –NHC] X 2（X = Br或Cl，n = 2–4）烷烃桥的螯合NHC-钯配合物。三唑基-N-杂环卡宾供体配体。X射线晶体学表征n = 2和3的溴化物配合物。研究了桥键和卤化物配体的长度对加氢胺化反应催化活性的影响。丙烯桥式Pd-NHC溴化物配合物2观察到最佳的催化性能。的加氢胺化苯乙炔 或者 4-甲基苯基乙炔用2催化的各种取代苯胺仅以良好的收率产生了马尔科夫尼科夫加成产物。有趣的是，这种均相催化剂可以重复使用三遍，而不会显着降低活性。
• Synthesis of novel carbohydrate-based valine-derived formamide organocatalysts by CuAAC click chemistry and their application in asymmetric reduction of imines with trichlorosilane
  作者：Xin Ge、Chao Qian、Xinzhi Chen

  DOI：10.1016/j.tetasy.2014.10.003

  日期：2014.11

  organocatalysts combining carbohydrate and N-formyl-l-valine derivatives were prepared by CuII-catalyzed diazo transfer and CuI-catalyzed azide–alkyne 1,3-dipolar cycloaddition CuAAC click chemistry. It was found that the carbohydrate-based valine-derived formamide organocatalyst had high catalytic activity for the asymmetric reduction of imines with trichlorosilane. The reduction can proceed at room

  结合碳水化合物和新颖有机催化剂Ñ甲酰基-L-缬氨酸衍生物通过制备铜II催化的重氮基转移和Cu我催化的叠氮化物-炔烃的1,3-偶极环加成CuAAC点击化学。据发现，所述碳水化合物基缬氨酸衍生的甲酰胺有机催化剂具有高的催化活性的不对称还原用三氯亚胺。还原可在室温下，在以高收率进行甲苯（高达98％）和具有优异的对映选择性（高达94％）。“CuAAC”点击化学是一个桥链路Ñ甲酰基-L-缬氨酸衍生碳水化合物有机催化剂。
• Synthesis of Group 4 Metal Complexes Stabilized by an Amine-Bridged Bis(phenolato) Ligand and Their Catalytic Behavior in Intermolecular Hydroamination Reactions
  作者：Qiu Sun、Yaorong Wang、Dan Yuan、Yingming Yao、Qi Shen

  DOI：10.1021/om401158a

  日期：2014.2.24

  bis(phenolato) ligand, have been synthesized and characterized. Although 1 and 2 were inactive in catalyzing intermolecular hydroamination reactions, cationic complexes generated in situ from treatment of 1 and 2 with borate [Ph3C][B(C6F5)4], respectively, were found to be highly active. In general, excellent yields (up to >99%) and 100% regioselectivity for a broad range of terminal alkynes and anilines

  锆和钛配合物1和2，带有胺桥连双（苯酚）配体，已经合成和表征。虽然1和2无活性在催化分子间加氢胺化反应，从治疗的原位产生的阳离子络合物1和2与硼酸[PH 3 C] [B（C 6 ˚F 5）4]分别被认为是高度活性的。一般情况下，优异的产率（高达> 99％）和为广泛末端炔烃和苯胺的100％的区域选择性分别为1个小时的反应时间内观察到。反应中度空间相互作用也导致了良好的收益率和适度的区域选择性的内部炔烃。动力学研究还进行，其提供了一些见解加氢胺化反应的机制。
• Asymmetric reduction of imines with trichlorosilane catalyzed by valine-derived formamide immobilized onto magnetic nano-Fe₃O₄
  作者：Xin Ge、Chao Qian、Xiaoming Ye、Xinzhi Chen

  DOI：10.1039/c5ra08516k

  日期：——

  were synthesized by anchoring valine-derived formamide onto the surface of Fe3O4 magnetic nanoparticles, which were applied in the asymmetric reduction of imines with trichlorosilane at room temperature in toluene. The high level of yield and enantioselectivity catalyzed by magnetic nano-Fe3O4-supported organocatalysts was obtained. In the immobilization process, CuI-catalyzed azide-alkyne 1,3-dipolar

  通过将缬氨酸衍生的甲酰胺固定在Fe 3 O 4磁性纳米颗粒的表面上，合成了磁性纳米Fe 3 O 4负载的有机催化剂，并将其应用于室温下用三氯硅烷在甲苯中不对​​称还原亚胺。获得了磁性纳米Fe 3 O 4负载的有机催化剂催化的高产率和对映选择性。在固定过程中，Cu I催化的叠氮化物-炔烃1,3-偶极环加成（CuAAC）“点击化学”用作锚定桥。磁性纳米颗粒可以简化有机催化剂的回收及其从反应体系中的分离。通过外部磁体，催化剂可以循环使用五次，而活性没有明显下降。
• Gallium Trichloride Catalyzed Hydroamination of Alkynes: Scope, Limitation, and Mechanistic Studies by DFT
  作者：Lei Li、Genping Huang、Zhou Chen、Wei Liu、Xiufang Wang、Yanmei Chen、Lijuan Yang、Wu Li、Yahong Li

  DOI：10.1002/ejoc.201200829

  日期：2012.10

  The successful application of gallium trichloride as a catalyst for the intermolecular hydroamination of alkynes with aromatic amines is reported. The reaction is effective with many aniline derivatives and shows exclusive selectivity for the Markovnikov products. The mechanism of the transformation was investigated by DFT calculations and a plausible pathway is proposed.

  报道了三氯化镓作为催化剂用于炔烃与芳胺分子间加氢胺化的成功应用。该反应对许多苯胺衍生物是有效的，并且对马尔科夫尼科夫产物显示出独特的选择性。通过 DFT 计算研究了转化的机制，并提出了一个合理的途径。