3-(phenyliminomethyl)phenol | 13206-60-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-(phenyliminomethyl)phenol
• 英文别名: N-(m-hydroxybenzylidene)aniline；m-hydroxybenzylideneaniline
• CAS: 13206-60-5；41097-59-0
• 化学式: C₁₃H₁₁NO
• 分子量: 197.236
• InChiKey: QTLFYSBCTXDWKE-GXDHUFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.59
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-(phenyliminomethyl)phenol 在 二氢吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以86%的产率得到3-(苯胺并甲基)苯酚
  参考文献：
  名称：

  Thiourea-Catalyzed Transfer Hydrogenation of Aldimines

  摘要：

  本信报告了以 1,4-二氢吡啶为氢源，通过氢键活化硫脲催化亚胺的转移加氢反应。在无酸和无金属的反应条件下，各种芳香族和脂肪族醛亚胺都能被还原生成相应的胺。

  DOI：

  10.1055/s-2007-980349
• 作为产物：
  描述：

  N-phenyl-α-(3-hydroxyphenyl)nitrone 、 劳森试剂 以39%的产率得到
  参考文献：
  名称：

  JORGENSEN K. A.; SHABANA R.; SCHEIBYE S.; LAWESSON S.-O., BULL. SOC. CHIM. BELG., 1980, 89, NO 3, 247-253

  摘要：

  DOI：

文献信息

• The evaluation of the role of C–H⋯F hydrogen bonds in crystal altering the packing modes in the presence of strong hydrogen bond
  作者：Gurpreet Kaur、Sandhya Singh、Amritha Sreekumar、Angshuman Roy Choudhury

  DOI：10.1016/j.molstruc.2015.10.105

  日期：2016.2

  found to form strong O–H⋯N hydrogen bond, but the spatial arrangement of the molecules connected by this hydrogen bond have been found to be controlled by the weak C–H⋯F and C–H⋯O hydrogen bonds, weak C–H⋯π and π⋯π interactions. This manuscript illustrates the importance of several weaker interactions in altering the packing modes in the presence of strong hydrogen bonds.

  摘要 涉及氟的相互作用是当代研究的一个领域。为了阐明强氢键存在下有机化合物中弱 C-H⋯F 氢键和 C-H⋯π 相互作用的重要性，合成了一系列同时具有羟基 (-OH) 和氟取代的 N-亚苄基苯胺，用于结构分析。这些化合物已通过实验性单晶 X 射线衍射分析和计算方法（Gaussian09 和 AIM2000）进行了研究。发现所有分子中存在的羟基形成强的 O-H⋯N 氢键，但发现由这种氢键连接的分子的空间排列受弱 C-H⋯F 和 C- H⋯O 氢键，弱 C–H⋯π 和 π⋯π 相互作用。
• [EN] NOVEL (1,3-BUTADIEN-2-YL)METHYLAMINE DERIVATIVES AND PREPARATION METHOD THEREOF<br/>[FR] NOUVEAUX DÉRIVÉS DE (1,3-BUTADIÈNE-2-YL)MÉTHYLAMINE ET PROCÉDÉ DE PRÉPARATION DE CEUX-CI
  申请人：KNU INDUSTRY COOPERATION FOUND

  公开号：WO2010035948A1

  公开（公告）日：2010-04-01

  The present invention provides a novel (1,3-butadien-2-yl)methylamine derivative and a preparation method thereof. The (1,3-butadien-2-yl)methylamine derivative having the 1,3-diene substituent at the alpha-position is an useful precursor in preparing various amine compounds having biochemical activities.

  本发明提供了一种新颖的(1,3-丁二烯-2-基)甲胺衍生物及其制备方法。具有1,3-二烯取代基位于α位的(1,3-丁二烯-2-基)甲胺衍生物是制备具有生物化学活性的各种胺类化合物的有用前体。
• Cerium(IV)-Promoted Ethylation of Schiff Bases by Triethylaluminum
  作者：Jochanan Blum、Dmitry Tsvelikhovsky、Herbert Schumann

  DOI：10.1055/s-2006-942379

  日期：2006.6

  Schiff bases Ar1CH=NAr2 that are refractory towards Et3Al are activated at room temperature by cerium(IV) compounds. The ethylation takes place selectively at the methine moiety of the imine. The process is strongly influenced by steric hindrance and depends on the electronic nature of the substrate: electron-donating substituents promote the reaction while electron-withdrawing groups cause it to slow down. Application of cerium(IV) ammonium nitrate as promoter gives the best results. In the absence of excess Et3Al it causes, however, transformation of the Schiff base to the corresponding aldehydes and amines.

  铈（IV）化合物可在室温下激活对 Et3Al 具有耐受性的希夫碱 Ar1CH=NAr2。乙化作用选择性地发生在亚胺的甲基上。这一过程受到立体阻碍的强烈影响，并取决于底物的电子性质：供电子的取代基会促进反应，而抽电子的基团则会导致反应减慢。使用硝酸铵铈（IV）作为促进剂能产生最佳效果。不过，在没有过量 Et3Al 的情况下，它会导致希夫碱转化为相应的醛和胺。
• The antioxidant effect of imine resveratrol analogues
  作者：Jing Lu、Chang Li、Yun-Feng Chai、De-Yu Yang、Cui-Rong Sun

  DOI：10.1016/j.bmcl.2012.06.026

  日期：2012.9

  Twenty five Imine resveratrol analogues (IRAs) were synthesized, replacing the C=C bond in resveratrol with C=N bond, as well as substitution modifications on aromatic rings. Radical scavenging activities against DPPH, along with singlet oxygen quenching capacities were evaluated, and further confirmed using density functional theory calculations (DFT). It was found that IRAs bearing ortho-OH on B ring have better radical scavenging activities against DPPH than resveratrol, these compounds were also found to be effective O-1(2) quenchers. Theoretical studies on the reaction mechanism of these compounds with O-1(2) suggest that the 1,3-addition to a double bond with a -OH group with the formation of allylic hydroperoxide is the most probable reaction route. (C) 2012 Elsevier Ltd. All rights reserved.
• US4153722A
  申请人：——

  公开号：US4153722A

  公开（公告）日：1979-05-08