N³-benzyl-1-phenyl-1H-1,2,4-triazole-3,5-diamine | 541500-17-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N³-benzyl-1-phenyl-1H-1,2,4-triazole-3,5-diamine
• 英文别名: 5-amino-3-benzylamino-1-phenyl-1,2,4-triazole；N3-benzyl-1-phenyl-1H-[1,2,4]triazole-3,5-diamine；3-N-benzyl-1-phenyl-1,2,4-triazole-3,5-diamine
• CAS: 541500-17-8
• 化学式: C₁₅H₁₅N₅
• mdl: MFCD04217186
• 分子量: 265.318
• InChiKey: QZNLCEJBJFUGTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  68.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对甲苯磺酰氯 、 N³-benzyl-1-phenyl-1H-1,2,4-triazole-3,5-diamine 在 吡啶 作用下， 以 乙腈 为溶剂， 以84%的产率得到5-amino-3-(N-benzyl-N-p-toluenesulfonyl)amino-1-phenyl-1,2,4-triazole
  参考文献：
  名称：

  Acyl and Sulfonyl Derivatives of 3,5-Diamino-1-R-1,2,4-triazoles

  摘要：

  DOI：

  10.1007/s10593-005-0293-2
• 作为产物：
  描述：

  5-amino-3-benzylideneamino-1-phenyl-1,2,4-triazole 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以70%的产率得到N³-benzyl-1-phenyl-1H-1,2,4-triazole-3,5-diamine
  参考文献：
  名称：

  Acyl and Sulfonyl Derivatives of 3,5-Diamino-1-R-1,2,4-triazoles

  摘要：

  DOI：

  10.1007/s10593-005-0293-2

文献信息

• Reactivity of<i>C</i>-Amino-1,2,4-triazoles toward Electrophiles: A Combined Computational and Experimental Study of Alkylation by Halogen Alkanes
  作者：Victor M. Chernyshev、Anna G. Vlasova、Alexander V. Astakhov、Svitlana V. Shishkina、Oleg V. Shishkin

  DOI：10.1021/jo502405q

  日期：2015.1.2

  3-amino- than for the 5-amino-1H-1,2,4-triazoles. Increasing electrophile hardness should increase the probability of attack at the N-4 atom of the triazole ring, whereas increasing softness should enhance the probability of attack at the N-2 atom and 3-NH2 group. Calculated transition state energies of model SN2 reactions and experimental studies showed that quaternization of 1-substituted 3-amino- and

  计算和实验方法的组合用于检查C-氨基-1 H -1,2,4-三唑与亲电试剂反应的结构-反应关系。预测3-氨基-和3,5-二氨基-1 H -1,2,4-三唑的整体亲核性高于5-氨基-1 H -1,2,4-三唑的整体亲核性。Fukui函数和分子静电势表明，与5-氨基-1 H -1,2,4-三唑相比，3-氨基-涉及氨基的反应更容易发生。亲电子硬度的增加应增加在三唑环的N-4原子处发生进攻的可能性，而柔软性的增加应在N-2原子和3-NH处发生进攻的可能性2组。计算的模型S N 2反应的过渡态能和实验研究表明，许多烷基卤化物对1-取代的3-氨基-和3,5-二氨基-1 H -1,2,4-三唑进行季铵化反应的选择性低，且可以涉及N-2和N-4原子以及3-NH 2基团作为反应中心。一种基于容易获得的1-取代的3-乙酰氨基-1,2,4-季铵化的选择性合成1,4-二取代的3-氨基-和3,5-二氨基-1,2,4
• A novel one-pot synthesis of 1,2,4-triazole-3,5-diamine derivatives from isothiocyanates and mono-substituted hydrazines
  作者：Chunjian Liu、Edwin J. Iwanowicz

  DOI：10.1016/s0040-4039(02)02871-x

  日期：2003.2

  1,2,4-Triazole-3,5-diamine derivatives were synthesized in moderate to high yields in one-pot reaction from the corresponding isothiocyanates, mono-substituted hydrazines, and sodium hydrogencyanamide, in the presence of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. Typically, two target compounds were obtained, but high regioselectivities to one isomer were observed when aromatic and

  在1-（3-二甲基氨基丙基）存在下，由一锅反应由相应的异硫氰酸酯，单取代的肼和氢氰胺钠以中等至高收率合成1,2,4-三唑-3,5-二胺衍生物）-3-乙基碳二亚胺盐酸盐。典型地，获得两种目标化合物，但是当使用芳族和空间上大体积的肼时，观察到对一种异构体的高区域选择性。给出了许多带有详细代表程序的示例。
• DIAMINOTRIAZOLES USEFUL AS INHIBITORS OF PROTEIN KINASES
  申请人：Pierce C. Albert

  公开号：US20080014189A1

  公开（公告）日：2008-01-17

  The present invention relates to inhibitors of protein kinases. The invention also provides pharmaceutical compositions comprising the compounds of the invention and methods of using the compositions in the treatment of various disorders.

  本发明涉及蛋白激酶抑制剂。该发明还提供了包含本发明化合物的药物组合物以及使用该组合物治疗各种疾病的方法。
• Alkylation of acyl and sulfonyl derivatives of 3,5-diamino-1-phenyl-1,2,4-triazole
  作者：V. M. Chernyshev、V. A. Rakitov、V. V. Blinov、V. A. Taranushich、Z. A. Starikova

  DOI：10.1007/s10593-009-0290-y

  日期：2009.4

  Alkylation of 3-acylamino-, 5-amino-1-phenyl-3-tosylamino-1,2,4-triazoles and 3,5-diacetylamino-1-phenyl-1,2,4-triazole in the presence of an equimolar amount of sodium methylate in DMSO occurs regioselectively at the amide (sulfamide) group nitrogen atom. The benzylation of 3-acetylamino-5-amino-1-phenyl-1,2,4-triazole with excess base and benzyl chloride also alkylates the amino group at position 5. Alkylamino-1-R-1,2,4-triazoles can be conveniently prepared by alkylation of the corresponding acetylamino-1,2,4-triazoles in the presence of base and subsequent acid hydrolysis of the N-acetyl-N-alkyl derivatives.
• Methods and Compositions for the Treatment of RAS Associated Disorders
  申请人：Ratner Nancy

  公开号：US20120302581A1

  公开（公告）日：2012-11-29

  The instant disclosure relates to compositions that may be useful as therapeutic agents for the treatment of disorders associated or caused by Ras deregulation or dysregulation, for example, disorders associated with alterations in the NF1 gene such as neurofibromatosis type I, fungal infections such as those caused by Candida albicans , and proliferative disorders such as glioblastoma.