N-苄基-2-(2-硝基苯基)乙胺 | 5339-07-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-苄基-2-(2-硝基苯基)乙胺
• 英文名称: 2-(ortho-nitrophenyl)-N-benzylethylamine
• 英文别名: N-2-(2-nitrophenyl)ethylbenzylamine；N-benzyl-2-(2-nitrophenyl)ethan-1-amine；benzyl-(2-nitro-phenethyl)-amine；Benzyl-(2-nitro-phenaethyl)-amin；n-Benzyl-2-(2-nitrophenyl)ethanamine
• CAS: 5339-07-1
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: DJEFWEWOFVLRPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-苄基-2-(2-硝基苯基)乙胺 在 palladium on activated charcoal 盐酸 、 氢气 、 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 反应 9.0h， 生成 ethyl N-<2-(2-aminophenyl)ethyl>glycinate
  参考文献：
  名称：

  Cylic guanidines. VIII. Synthesis of imidazo-1,3- and -2,4-benzodiazepine derivatives as blood platelet aggregation inhibitors.

  摘要：

  咪唑并[2,1-b][1,3]和-[2,4]苯并二氮杂卓-2-酮衍生物（4）和（13）以及咪唑并[1,2-α][1,3]苯并二氮杂卓-2-酮衍生物（9）是一种强效的血小板聚集抑制剂，咪唑并[2,1-b]喹唑啉-2-酮衍生物（14）是环扩张类似物。化合物9表现出强效活性，但4和13分别表现出低效活性和无活性。

  DOI：

  10.1248/cpb.28.1307
• 作为产物：
  描述：

  2-(2-硝基苯基)乙胺 、 苯甲醛 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 N-苄基-2-(2-硝基苯基)乙胺
  参考文献：
  名称：

  Design and synthesis of benzoazepin-2-one analogs as allosteric binders targeting the PIF pocket of PDK1

  摘要：

  A novel series of benzoazepin-2-ones were designed and synthesized targeting the PIF pocket of AGC protein kinases, among which a series of thioether-linked benzoazepin-2-ones were discovered to bind to the PIF pocket of 3-phosphoinositide- dependent kinase-1 (PDK1), and to displace the PIF peptide with an EC(50) values in the lower micromolar range. The structure-activity relationships (SARs) of the linker region, tail region, and distal region were explored to further optimize these novel binders which target the PIF pocket of PDK1. When tested in an in vitro PDK1 enzymatic assay using a peptide substrate, the benzodiazepin-2-ones increased the activity of the enzyme in a concentration-dependent fashion, indicating these compounds act as PDK1 allosteric activators. These new compounds may be further developed as therapeutic agents for the treatment of diseases where the PDK1-mediated AGC protein kinases are dysregulated. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.05.019

文献信息

• Nucleophilic additions to polarized vinylarenes
  作者：Krishna Kumar Gnanasekaran、Junghak Yoon、Richard A. Bunce

  DOI：10.1016/j.tetlet.2016.06.033

  日期：2016.7

  substituents on the side chain double bond. The study revealed that nitro substitution gave the best results for addition of carbon and nitrogen nucleophiles. Cyano-substituted systems added carbon nucleophiles, but underwent polymerization or degradation with nitrogen nucleophiles. Ethoxycarbonyl-bearing substrates reacted primarily at the ester carbonyl. The reaction generally proceeded well with methyl

  将亲核试剂加到在邻位或对位结合了吸电子基团的苯乙烯的末端双键碳上位置已被研究。已经优化了该转化的条件，并且已经探索了对底物的结构修饰。结构变化包括芳环上活化基的变化和侧链双键上的定位取代基。研究表明，硝基取代对于碳和氮亲核试剂的添加效果最佳。氰基取代的系统添加了碳亲核试剂，但是经过了氮亲核试剂的聚合或降解。带有乙氧基羰基的底物主要在酯羰基上反应。通常，在双键的α碳上有甲基的情况下，反应进行得很好，但在β位置的甲基会使反应变慢。对于22个实例，产率从50％变化到97％。
• N-Substituted 1-Aminoindoles from ElectrogeneratedN-Substituted 2-(ortho-Nitrosophenyl)ethylamines
  作者：B. A. Frontana-Uribe、C. Moinet、L. Toupet

  DOI：10.1002/(sici)1099-0690(199902)1999:2<419::aid-ejoc419>3.0.co;2-v

  日期：1999.2
• Design and synthesis of benzoazepin-2-one analogs as allosteric binders targeting the PIF pocket of PDK1
  作者：Linyi Wei、Xiaoqi Gao、Robert Warne、Xueshi Hao、Dirksen Bussiere、Xiang-ju Gu、Tetsuo Uno、Yi Liu

  DOI：10.1016/j.bmcl.2010.05.019

  日期：2010.7

  A novel series of benzoazepin-2-ones were designed and synthesized targeting the PIF pocket of AGC protein kinases, among which a series of thioether-linked benzoazepin-2-ones were discovered to bind to the PIF pocket of 3-phosphoinositide- dependent kinase-1 (PDK1), and to displace the PIF peptide with an EC(50) values in the lower micromolar range. The structure-activity relationships (SARs) of the linker region, tail region, and distal region were explored to further optimize these novel binders which target the PIF pocket of PDK1. When tested in an in vitro PDK1 enzymatic assay using a peptide substrate, the benzodiazepin-2-ones increased the activity of the enzyme in a concentration-dependent fashion, indicating these compounds act as PDK1 allosteric activators. These new compounds may be further developed as therapeutic agents for the treatment of diseases where the PDK1-mediated AGC protein kinases are dysregulated. (c) 2010 Elsevier Ltd. All rights reserved.
• Cylic guanidines. VIII. Synthesis of imidazo-1,3- and -2,4-benzodiazepine derivatives as blood platelet aggregation inhibitors.
  作者：FUMIYOSHI ISHIKAWA、YOSHIFUMI WATANABE

  DOI：10.1248/cpb.28.1307

  日期：——

  The imidazo [2, 1-b] [1, 3]- and -[2, 4] benzodiazepin-2-one derivatives (4) and (13), and imidazo [1, 2-α] [1, 3] benzodiazepin-2-one derivative (9), of a potent blood platelet aggregation inhibitor, the imidazo [2, 1-b] quinazolin-2-one derivative (14), were synthesized as ring expansion analogs. Compound 9 showed potent activity but 4 and 13 showed poor activity and no activity, respectively.

  咪唑并[2,1-b][1,3]和-[2,4]苯并二氮杂卓-2-酮衍生物（4）和（13）以及咪唑并[1,2-α][1,3]苯并二氮杂卓-2-酮衍生物（9）是一种强效的血小板聚集抑制剂，咪唑并[2,1-b]喹唑啉-2-酮衍生物（14）是环扩张类似物。化合物9表现出强效活性，但4和13分别表现出低效活性和无活性。