N-benzyl-N'-phenyl-p-phenylenediamine | 13556-73-5

• 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-benzyl-N'-phenyl-p-phenylenediamine
• 英文别名: N-Benzyl-N'-phenyl-p-phenylendiamin；N-phenyl-N'-benzyl-p-phenylenediamine；Phenyl-<4-benzylamino-phenyl>-amin；4-Benzylamino-diphenylamin；N-Benzyl-N'-phenyl-p-phenylenediamine；1-N-benzyl-4-N-phenylbenzene-1,4-diamine
• CAS: 13556-73-5
• 化学式: C₁₉H₁₈N₂
• 分子量: 274.365
• InChiKey: CKVFMHUYNFWPAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(氯磺酰)苯甲酸 、 N-benzyl-N'-phenyl-p-phenylenediamine 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 4-[(4-Anilinophenyl)-benzylsulfamoyl]benzoic acid
  参考文献：
  名称：

  Synthesis and pharmacological characterization of benzenesulfonamides as dual species inhibitors of human and murine mPGES-1

  摘要：

  The microsomal prostaglandin E-2 synthase 1 (mPGES-1) became a desirable target in recent years for the research of new anti-inflammatory drugs. Even though many potent inhibitors of human mPGES-1, tested in vitro assay systems, have been synthesized, they all failed in preclinical trials in rodent models of inflammation, due to the lack of activity on rodent enzyme. Within this work we want to present a new class of mPGES-1 inhibitors derived from a benzenesulfonamide scaffold with inhibitory potency on human and murine mPGES-1. Starting point with an IC50 of 13.8 mu M on human mPGES-1 was compound 1 (4-{benzyl[(4-methoxyphenyl) methyl] sulfamoyl} benzoic acid; FR4), which was discovered by a virtual screening approach. Optimization during a structure-activity relationship (SAR) process leads to compound 28 (4-[(cyclohexylmethyl)[(4-phenylphenyl) methyl] sulfamoyl] benzoic acid) with an improved IC50 of 0.8 mu M on human mPGES-1. For the most promising compounds a broad pharmacological characterization has been carried out to estimate their anti-inflammatory potential. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.006
• 作为产物：
  描述：

  对氨基二苯胺 在 乙醇 、 sodium 作用下， 生成 N-benzyl-N'-phenyl-p-phenylenediamine
  参考文献：
  名称：

  Heucke, Justus Liebigs Annalen der Chemie, 1889, vol. 255, p. 191

  摘要：

  DOI：

文献信息

• Pt-Sn/γ-Al2O3-Catalyzed Highly Efficient Direct Synthesis of Secondary and Tertiary Amines and Imines
  作者：Wei He、Liandi Wang、Chenglin Sun、Kaikai Wu、Songbo He、Jiping Chen、Ping Wu、Zhengkun Yu

  DOI：10.1002/chem.201101725

  日期：2011.11.18

  syntheses of secondary and tertiary amines by highly efficient direct N‐alkylation of primary and secondary amines with alcohols or by deaminative self‐coupling of primary amines have been successfully realized by means of a heterogeneous bimetallic Pt–Sn/γ‐Al2O3 catalyst (0.5 wt % Pt, Pt/Sn molar ratio=1:3) through a borrowing‐hydrogen strategy. In the presence of oxygen, imines were also efficiently prepared

  多功能通过高效直接伯和仲胺与醇或由deaminative自偶联的伯胺的已成功由多相双金属的Pt-Sn系来实现/γ-Al系的N-烷基化仲胺和叔胺的合成2 ö 3催化剂（0.5 wt％Pt，Pt / Sn摩尔比= 1：3）通过借位氢策略。在氧气存在下，还可以通过胺与醇或两种伯胺之间的串联反应有效地制备亚胺。所提出的机理表明，醇或胺底物最初会脱氢成醛/酮或NH-亚胺，并同时形成[PtSn]氢化物。醛/酮物种的缩合或NH-亚胺中间体与另一种胺分子的脱氨基反应形成N-取代的亚胺，然后在氮气氛下原位生成的[PtSn]氢化物将其还原为新的胺产物最终产品在氧气气氛下保持不变。将Pt-Sn系/γ-Al系2 ö 3 该催化剂可轻松回收利用，而无需进行Pt金属的浸出，并且对多种胺和醇类底物表现出非常高的催化活性，这表明其在直接生产仲胺和叔胺以及N-取代的亚胺中的应用潜力。
• Reduction and Benzylation by Means of Benzyl Alcohol. II. N-Benzylation. The Preparation of Secondary Aromatic Benzylamines
  作者：Yaër Sprinzak

  DOI：10.1021/ja01594a064

  日期：1956.7
• Stabilized polyolefin compositions
  申请人：Kumar Vijayendra

  公开号：US20070149660A1

  公开（公告）日：2007-06-28

  Disclosed are compositions comprising antioxidants and stabilizers, such as, acid scavengers or organic phosphorus stabilizers, and optionally further comprising co-stabilizers. The disclosed compositions are useful as stabilizers for polyolefins and other polymeric materials. The disclosed compositions and methods generally provide longer shelf lifes and better oxidative resistance to materials than currently available antioxidants.
• Lubricant oil compositions
  申请人：Cholli L. Ashok

  公开号：US20070161522A1

  公开（公告）日：2007-07-12

  Compositions comprise first antioxidants and first additives, such as, a surface additives, performance enhancing additives and lubricant protective additives and optionally second additives and/or second antioxidants. The compositions are useful to improve lubricants, lubricant oils and other lubricant materials. The compositions and methods generally provide longer shelf lives, increased oxidative resistance, improved quality and/or enhanced performance to lubricants or lubricant oils.
• Lubricant Oil Compositions
  申请人：Cholli Ashok L.

  公开号：US20120004150A1

  公开（公告）日：2012-01-05

  Compositions comprise first antioxidants and first additives, such as, a surface additives, performance enhancing additives and lubricant protective additives and optionally second additives and/or second antioxidants. The compositions are useful to improve lubricants, lubricant oils and other lubricant materials. The compositions and methods generally provide longer shelf lives, increased oxidative resistance, improved quality and/or enhanced performance to lubricants or lubricant oils.

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