4-Methyl-benzylcyanamid | 98952-71-7

• 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: 4-Methyl-benzylcyanamid
• 英文别名: (4-Methylbenzyl)cyanamide；(4-methylphenyl)methylcyanamide
• CAS: 98952-71-7
• 化学式: C₉H₁₀N₂
• mdl: MFCD16767999
• 分子量: 146.192
• InChiKey: AORXOALXSRJQEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  4-Methyl-benzylcyanamid 在 羟胺 作用下， 以 甲醇 为溶剂， 生成 1-Hydroxy-2-[(4-methylphenyl)methyl]guanidine
  参考文献：
  名称：

  Electrochemical and peroxidase oxidation study of N′-Hydroxyguanidine derivatives as NO donors

  摘要：

  The electrochemical properties of a series of N-substituted-N-hydroxyguanidines were studied. Two oxidation potentials of each compound were obtained by cyclic voltammetry. The E-ox1 values were from 0.51 to 0.62V, while the E-ox2 Values were from 1.14 to 1.81V in acetonitrile solution. Next, their enzymatic controlled NO release abilities were evaluated. All N'-hydroxyguanidines exhibited efficient NO release abilities under the oxidation by horseradish peroxidase in the presence Of H2O2. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00185-3
• 作为产物：
  描述：

  溴化氰 、 4-甲基苄胺 以 乙醚 为溶剂， 生成 4-Methyl-benzylcyanamid
  参考文献：
  名称：

  Electrochemical and peroxidase oxidation study of N′-Hydroxyguanidine derivatives as NO donors

  摘要：

  The electrochemical properties of a series of N-substituted-N-hydroxyguanidines were studied. Two oxidation potentials of each compound were obtained by cyclic voltammetry. The E-ox1 values were from 0.51 to 0.62V, while the E-ox2 Values were from 1.14 to 1.81V in acetonitrile solution. Next, their enzymatic controlled NO release abilities were evaluated. All N'-hydroxyguanidines exhibited efficient NO release abilities under the oxidation by horseradish peroxidase in the presence Of H2O2. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00185-3

文献信息

• Nano Cerium Oxide as a Recyclable Catalyst for the Synthesis of <i>N</i>-Monosubstituted Ureas with the Aid of Acetaldoxime as an effective Water Surrogate
  作者：S. Mohammad Sajadi、Mehdi Maham

  DOI：10.3184/174751913x13787959859461

  日期：2013.10

  A new method for the synthesis of N-monosubstituted ureas has been developed by the reaction of cyanamides with acetaldoxime in the presence of nano cerium oxide as an efficient and recyclable catalyst.

  在纳米氧化铈作为一种高效且可回收的催化剂存在下，通过氰胺与乙醛肟的反应，开发了一种合成 N-单取代脲的新方法。
• Copper and In Situ-Generated Triflic Acid Relay-Promoted Four-Component Cascade Reaction for the Construction of Polysubstituted Cycloguanidines
  作者：Yiming Zhao、Run Yang、Canming Wu、Shihan Wang、Xinghua Liu、Jihui Li、Shuying Xu

  DOI：10.1021/acs.joc.3c00415

  日期：2023.7.7

  An unprecedented copper and in situ-generated triflic acid relay-promoted four-component cascade reaction of cyanamides, diaryliodonium triflates, propargylic amines, and H2O was established for rapid and concise construction of diverse five-membered cycloguanidines. Copper-catalyzed guanidination/intramolecular hydroamination and in situ-generated HOTf-accelerated hydration proceeded sequentially

  建立了前所未有的铜和原位生成的三氟甲磺酸中继促进的氰胺、二芳基碘鎓三氟甲磺酸盐、炔丙胺和H 2 O的四组分级联反应，用于快速、简洁地构建多种五元环胍。铜催化的胍基化/分子内氢胺化和原位生成的HOTf加速水合顺序进行，具有高水平的化学选择性和区域选择性，并且以高产率同时构建了6个新键。因此，二芳基碘鎓三氟甲磺酸盐不仅用作芳基化试剂，而且还用作内部酸促进剂，为高效利用二芳基碘鎓三氟甲磺酸盐建立了替代策略。
• Novel substrates for nitric oxide synthases
  作者：Ming Xian、Noriko Fujiwara、Zhong Wen、Tingwei Cai、Satoshi Kazuma、Adam J Janczuk、Xiaoping Tang、Vladislav V Telyatnikov、Yingxin Zhang、Xinchao Chen、Yasuhide Miyamoto、Naoyuki Taniguchi、Peng George Wang

  DOI：10.1016/s0968-0896(02)00155-4

  日期：2002.9

  Enzymatic generation of nitric oxide (NO) by nitric oxide synthase (NOS) consists of two oxidation steps. The first step converts L-arginine to N-G-hydroxy-L-arginine (NOHA), a key intermediate, and the second step converts NOHA to NO and L-citrulline. To fully probe the substrate specificity of the second enzymatic step, an extensive structural screening was carried out using a series of N-alkyl (and N-aryl) substituted-N'-hydrosyguanidines (1-14). Among the eleven N-alkyl-N'-hydroxyguanidines evaluated, N-n-propyl (2). N-iso-propyl (3). N-n-butyl (4). N-s-butyl (5). N-iso-butyl (6), N-pentyl (8) and N-iso-pentyl (9) derivatives were efficiently oxidized by the three isoenzymes of NOS (nNOS, iNOS and eNOS) to generate NO. N-Butyl-N'-hydroxyguanidine (4) was the best substrate for iNOS (K-m = 33 muM) and N-iso-propyl-N'-hydroxyguanidine (3) was the best substrate for nNOS (K-m = 56 muM). When the alkyl substituents were too small (such as ethyl 1) or too large (such as hexyl 10 and cyclohexyl 11) the activity decreased significantly. This suggests that the van der Waals interaction between the alkyl group and the hydrophobic cavity in the NOS active site contributes significantly to the relative reactivity of compounds 3-11. Moreover, five N-aryl-N'-hydroxyguanidines were found to be good substrates for iNOS. but not substrates for eNOS and nNOS. N-phenyl-N'-hydroxy- guanidine was the best substrate among them (K-m = 243 muM). This work demonstrates that N-alkyl substituted hydroxyguanidine compounds are novel NOS substrates which 'short-circuit' the first oxidation step of NOS, and N-aryl substituted hydroxyguanidine compounds are isoform selective NOS substrate. (C) 2002 Published by Elsevier Science Ltd.