1-benzyl-3-phenylguanidine | 56497-11-1

• 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: 1-benzyl-3-phenylguanidine
• 英文别名: N-benzyl-N'-phenyl-guanidine；N-Benzyl-N'-phenyl-guanidin；2-Benzyl-1-phenylguanidine
• CAS: 56497-11-1
• 化学式: C₁₄H₁₅N₃
• mdl: MFCD17964693
• 分子量: 225.293
• InChiKey: QCKAIBFKGRYYAX-UHFFFAOYSA-N

物化性质

• 熔点：
  122-123 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  351.3±35.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-phenylguanidine 以 苯 为溶剂， 反应 2.0h， 生成 (4-Benzylamino-2-p-tolylamino-thiazol-5-yl)-phenyl-methanone
  参考文献：
  名称：

  Rajasekharan, K. N.; Sulekha, A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 7, p. 549 - 551

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(苄基氨基甲酰基)氨基甲酸乙酯 在 三甲基溴硅烷 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 三乙胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 1-benzyl-3-phenylguanidine
  参考文献：
  名称：

  A highly efficient method for the synthesis of guanidinium derivatives

  摘要：

  A high yielding synthesis of guanidiniums with the use of the ethyl carbamate protecting group is presented. This strategy eliminates many steric hindrance and electronic problems. The deprotection of the products by Me3SiBr is also demonstrated. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)02165-7

文献信息

• Novel linker for the solid-phase synthesis of guanidines
  作者：John A Josey、Catherine A Tarlton、Courtney E Payne

  DOI：10.1016/s0040-4039(98)01242-8

  日期：1998.8

  A novel linker for the generation of alkyl-, acyl- and arylguanidines as an attachment point in solid phase synthesis has been developed. Introduction of a suitably functionalized thiourea to Wang resin via a carbamate linkage, followed by displacement of sulfur with a 1° or 2° amine affords resin bound guanidines suitably protected for further manipulation. Activation of the thiourea with Mukaiyama's

  已经开发了用于生成烷基，酰基和芳基胍作为固相合成中的连接点的新型连接子。通过氨基甲酸酯键将适当官能化的硫脲引入到Wang树脂中，然后用1°或2°胺置换硫，从而得到树脂结合的胍，该胍被适当保护以用于进一步操作。用Mukaiyama试剂活化硫脲可生成芳基胍。温和的酸处理可使其脱保护并从树脂中释放出来，从而以高收率和高纯度提供胍。
• Copper(I) Iodide-Catalyzed Synthesis of N,N′-Disubstituted Guanidines from N-Substituted Cyanamides
  作者：Cian-Jhe Zeng、Chia-Jung Chen、Chih-Wei Chang、Hui-Ting Chen、Tun-Cheng Chien

  DOI：10.1071/ch14197

  日期：——

  A facile and effective synthesis of N-alkyl-N′-arylguanidines was accomplished by the reaction of N-arylcyanamides with various primary and secondary alkylamines, under the catalysis of copper(i) iodide and Xantphos in DMF. This methodology provides a direct access to versatile N,N′-disubstituted guanidine derivatives from N-arylcyanamides that can be readily prepared from the corresponding nitriles

  N-烷基-N'-芳基胍的简便有效合成是通过在DMF中碘化铜（i）和Xantphos的催化下，使N-芳基氰酰胺与各种伯和仲烷基胺反应来完成的。该方法提供了从N-芳基氰酰胺直接获得通用的N，N'-二取代胍衍生物的途径，这些衍生物可以通过Tiemann重排容易地由相应的腈制备。
• o-Iodoxybenzoic acid mediated oxidative condensation: synthesis of guanidines using 1,-3-disubstituted thiourea precursors
  作者：Prasad S. Dangate、Krishnacharya G. Akamanchi

  DOI：10.1016/j.tetlet.2012.09.130

  日期：2012.12

  An efficient and mild oxidative condensation procedure using o-iodoxybenzoic acid and triethylamine or ammonia as base has been developed for the synthesis of guanidines starting from easily synthesizable 1,3-disubstituted thioureas and amines or ammonia. (C) 2012 Elsevier Ltd. All rights reserved.
• Direct Guanidinylation of Aryl and Heteroaryl Halides via Copper-Catalyzed Cross-Coupling Reaction
  作者：Hassan Hammoud、Martine Schmitt、Frédéric Bihel、Cyril Antheaume、Jean-Jacques Bourguignon

  DOI：10.1021/jo202018w

  日期：2012.1.6

  A modified Ullmann reaction using p-methoxybenzyl (PMB) guanidine as guanidinylation agent yielded various aryl and heteroaryl guanidines in good yields.
• Partridge; Turner, Journal of Pharmacy and Pharmacology, 1953, vol. 5, p. 103,105
  作者：Partridge、Turner

  DOI：——

  日期：——