N-(3,4-dichlorophenyl)-benzenemethanamine | 51597-75-2

• 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: N-(3,4-dichlorophenyl)-benzenemethanamine
• 英文别名: N-benzyl-3,4-dichlorobenzenamine；N-benzyl-3,4-dichloroaniline
• CAS: 51597-75-2
• 化学式: C₁₃H₁₁Cl₂N
• mdl: MFCD01427001
• 分子量: 252.143
• InChiKey: PYRNSWQKFKLMLR-UHFFFAOYSA-N

物化性质

• 沸点：
  391.0±27.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：2-8°C，避光，惰性气体

反应信息

• 作为反应物：
  描述：

  N-(3,4-dichlorophenyl)-benzenemethanamine 、 氯乙酰氯 以 丙酮 为溶剂， 反应 1.5h， 生成 N-benzyl-2-chloro-N-(3,4-dichlorophenyl)acetamide
  参考文献：
  名称：

  Binding Mode Characterization and Early in Vivo Evaluation of Fragment-Like Thiols as Inhibitors of the Virulence Factor LasB from Pseudomonas aeruginosa

  摘要：

  The increasing emergence of antibiotic resistance necessitates the development of anti-infectives with novel modes of action. Targeting bacterial virulence is considered a promising approach to develop novel antibiotics with reduced selection pressure. The extracellular collagenase elastase (LasB) plays a pivotal role in the infection process of Pseudomonas aeruginosa and therefore represents an attractive antivirulence target. Mercaptoacetamide-based thiols have been reported to inhibit LasB as well as collagenases from MMPs clostridia and bacillus species. The present work provides an insight into the structure activity relationship (SAR) of these fragment-like LasB inhibitors, demonstrating an inverse activity profile compared to similar inhibitors of clostridial collagenase H (CoIH). An X-ray cocrystal structure is presented, revealing distinct binding of two compounds to the active site of LasB, which unexpectedly maintains an open conformation. We further demonstrate in vivo efficacy in a Galleria mellonella infection model and high selectivity of the LasB inhibitors toward human matrix metalloproteinases (MMPs).

  DOI：

  10.1021/acsinfecdis.8b00010
• 作为产物：
  描述：

  苯甲醛 、 3,4-二氯苯胺 在 二氢吡啶 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以94%的产率得到N-(3,4-dichlorophenyl)-benzenemethanamine
  参考文献：
  名称：

  磁性纳米粒子支撑的膦金（i）络合物：高效，可回收的催化剂，用于醛和酮的直接还原胺化†

  摘要：

  在室温下，使用磁性纳米粒子负载的膦金（I）络合物[Fe 3 O 4 @SiO 2 -P–AuCl]作为催化剂，并用乙基汉茨sch酯作为醛类，可以在二氯甲烷中实现醛和酮的直接还原胺化。氢源，可在中性条件下以优异的产率产生各种仲胺。新的多相金催化剂可以通过简单的方法由市售的试剂制备，并且可以通过施加外部磁体容易地与反应混合物分离，并循环至少10次而没有任何活性损失。

  DOI：

  10.1039/c5cy02159f

文献信息

• Pd@[nBu4][Br] as a Simple Catalytic System for N-Alkylation Reactions with Alcohols
  作者：Bastien Cacciuttolo、Oana Pascu、Cyril Aymonier、Mathieu Pucheault

  DOI：10.3390/molecules21081042

  日期：——

  Palladium nanoparticles, simply and briefly generated in commercial and cheap onium salts using supercritical carbon dioxide, have been found to be an effective catalytic system for additive free N-alkylation reaction using alcohols via cascade oxidation/condensation/reduction steps.

  使用超临界二氧化碳在商业和廉价的鎓盐中简单而简单地生成钯纳米颗粒，已被发现是使用醇通过级联氧化/缩合/还原步骤进行无添加剂 N-烷基化反应的有效催化系统。
• N-Alkylation of amines with alcohols over nanosized zeolite beta
  作者：Marri Mahender Reddy、Macharla Arun Kumar、Peraka Swamy、Mameda Naresh、Kodumuri Srujana、Lanka Satyanarayana、Akula Venugopal、Nama Narender

  DOI：10.1039/c3gc41345d

  日期：——

  Direct N-alkylation of amines with alcohols was successfully performed by using nanosized zeolite beta, which showed the highest catalytic activity among other conventional zeolites. This method has several advantages, such as eco-friendliness, moderate to high yields, and simple work-up procedure. The catalyst was successfully recovered and reused without significant loss of activity and only water is produced as co-product. In addition, imines were also efficiently prepared from the tandem reactions of amines with 2-, 3- and 4-nitrobenzyl alcohols using nanosized zeolite beta.

  使用纳米尺寸的Beta沸石成功实现了胺与醇的直接N-烷基化反应，Beta沸石在其他传统沸石中显示出最高的催化活性。该方法具有多个优点，如环保性、适中至高产率以及简便的后续处理程序。催化剂可成功回收并重复使用，活性无明显损失，副产物仅为水。此外，通过使用纳米尺寸的Beta沸石，胺与2-、3-和4-硝基苄醇的串联反应也能高效制备亚胺。
• Reinvestigating Raney nickel mediated selective alkylation of amines with alcohols via hydrogen autotransfer methodology
  作者：Astha Mehta、A. Thaker、V. Londhe、Santosh R. Nandan

  DOI：10.1016/j.apcata.2014.04.009

  日期：2014.5

  efficient, cost-effective use of Raney nickel (R-Ni) a widely used industrial catalyst for N-alkylation using alcohols is highlighted here. The work describes the scope and capability of R-Ni in hydrogen autotransfer reactions enabling its widespread use in the Chemical and Pharmaceutical industry. R-Ni of W4, T4, and W7 grades were prepared and evaluated for alkylation of amines. The best activity and

  本文重点介绍了阮内镍（R-Ni）（一种广泛使用的工业催化剂，用于使用醇进行N-烷基化）的高效，经济高效的使用。这项工作描述了R-Ni在氢自动转移反应中的范围和能力，使其能够在化学和制药工业中广泛使用。制备了W4，T4和W7级的R-Ni，并对其胺的烷基化进行了评估。使用W4 R-Ni，将胺与二甲苯中的醇以1：4摩尔的比例回流，可获得最佳的胺单烷基化活性和选择性。T4 R-Ni也显示出形成稳定亚胺的能力。所制备的R-Ni也被再循环并重新用于N-烷基化反应。优化的方法应用于活性药物成分比立地尔和美吡拉明的合成。
• Direct reductive amination of aldehydes with nitroarenes using bio-renewable formic acid as a hydrogen source
  作者：Qi Zhang、Shu-Shuang Li、Ming-Ming Zhu、Yong-Mei Liu、He-Yong He、Yong Cao

  DOI：10.1039/c5gc02583d

  日期：——

  Direct reductive amination of aldehydes with nitroarenes can be carried out efficiently in neat water in the presence of a single phase rutile titania supported gold catalyst using FA as the hydrogen donor.

  在单相金红石钛金催化剂的存在下，可以在纯净水中高效地进行醛和硝基芳烃的直接还原胺化反应，使用FA作为氢供体。
• The NMR spectra of the porphyrins. 17—Metalloporphyrins as diamagnetic shift reagents, structural and specificity studies
  作者：Raymond J. Abraham、Geoffrey R. Bedford、Brian Wright

  DOI：10.1002/mrc.1270180111

  日期：1982.1

  AbstractThe nature of the metalloporphyrin‐ligand complexes produced by zinc, magnesium and cobalt porphyrins with basic ligands has been investigated using the diamagnetic ring current shifts of the porphyrin on the ligand protons. The metal to nitrogen bond lengths in some metallo‐meso‐tetraphenylporphyrin (pyridine) complexes have been determined and compared with the data of the crystalline complexes. The geometry of the Zn meso‐tetraphenylporphyrin complexes with 2‐picoline, quinoline and isoquinoline has been investigated. Steric interactions between the ligand and the porphyrin in 2‐picoline and quinoline produce a dramatic increase in the ZnN bond length when compared to the unstrained analogues pyridine and isoquinoline. This large increase is associated with comparatively minor angle distortions in the complex. The specificity of the Zn meso‐tetraphenylporphyrin complexation shifts has been determined for a range of benzyl and butyl compounds. The complexation shift is linearly related to the basicity of the ligand for a wide range of basicities.