N-tolyl-N',N'-dimethylformamidine | 56638-68-7

• 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: N-tolyl-N',N'-dimethylformamidine
• 英文别名: N,N-dimethyl-N'-(4-methylphenyl)formamidine；(E)-N,N-dimethyl-N'-p-tolylformamidine；N,N-Dimethyl-N'-4-methylphenyl-formamidin
• CAS: 56638-68-7
• 化学式: C₁₀H₁₄N₂
• 分子量: 162.235
• InChiKey: NOBRDGQOCLNSSL-DHZHZOJOSA-N

物化性质

• 熔点：
  37-38 °C
• 沸点：
  163-165 °C(Press: 29-30 Torr)
• 密度：
  0.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.22
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  15.6
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-tolyl-N',N'-dimethylformamidine 在 盐酸羟胺 作用下， 以 甲醇 为溶剂， 生成 N′-hydroxy-N-(p-tolyl)formamidamide
  参考文献：
  名称：

  Discovery of a N′-hydroxyphenylformamidine derivative HET0016 as a potent and selective 20-HETE synthase inhibitor

  摘要：

  N-(4-Butyl-2-methylphenyl)-N'-hydroxyformamidine (HET0016) was evaluated as the first potent and selective inhibitor of 20-hydroxy-5,8,11,14-eicosatetraenoic acid (20-HETE) synthase. The IC50 value of HET0016 for the production of 20-HETE from arachidonic acid (AA) by human renal microsomes was 8.9 +/- 2.7 nM, with over 200 times the selectivity of xenobiotic-metabolizing cytochrome P450 enzymes. An examination of the structure-activity relationship revealed that the unsubstituted hydroxyformamidine moiety and the substituent at the para-position of the N-hydroxyformamidine moiety are necessary for the potent activity of HET0016. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00614-x
• 作为产物：
  描述：

  乙烷,三氯氟- 、 N,N-二甲基甲酰胺二甲基缩醛 以 甲苯 为溶剂， 生成 N-tolyl-N',N'-dimethylformamidine
  参考文献：
  名称：

  Discovery of a N′-hydroxyphenylformamidine derivative HET0016 as a potent and selective 20-HETE synthase inhibitor

  摘要：

  N-(4-Butyl-2-methylphenyl)-N'-hydroxyformamidine (HET0016) was evaluated as the first potent and selective inhibitor of 20-hydroxy-5,8,11,14-eicosatetraenoic acid (20-HETE) synthase. The IC50 value of HET0016 for the production of 20-HETE from arachidonic acid (AA) by human renal microsomes was 8.9 +/- 2.7 nM, with over 200 times the selectivity of xenobiotic-metabolizing cytochrome P450 enzymes. An examination of the structure-activity relationship revealed that the unsubstituted hydroxyformamidine moiety and the substituent at the para-position of the N-hydroxyformamidine moiety are necessary for the potent activity of HET0016. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00614-x

文献信息

• Formamidines - Versatile Ligands for Zinc-Catalyzed Hydrosilylation and Iron-Catalyzed Epoxidation Reactions
  作者：Stephan Enthaler、Kristin Schröder、Shigeyoshi Inoue、Björn Eckhardt、Kathrin Junge、Matthias Beller、Matthias Drieß

  DOI：10.1002/ejoc.201000648

  日期：2010.9

  In the present study the abilities of catalysts modified by formamidine ligands have been examined in the zinc-catalyzed hydrosilylation of ketones and the iron-catalyzed epoxidation of stilbene. In case of hydrosilylation diethylzinc combined with easily accessible formamidine ligands allow for the efficient reduction of various aryl and alkyl ketones. By using a convenient in situ catalyst system

  在本研究中，研究了甲脒配体修饰的催化剂在酮的锌催化氢化硅烷化和二苯乙烯的铁催化环氧化中的能力。在氢化硅烷化的情况下，二乙基锌与易于获得的甲脒配体相结合，可以有效还原各种芳基和烷基酮。通过使用方便的原位催化剂系统，实现了高达 1.000 h -1 以上的高周转频率和广泛的官能团耐受性。此外，甲脒配体以良好的收率和化学选择性成功应用于二苯乙烯与过氧化氢的铁催化环氧化反应。
• Oxidation of Primary Aromatic Amines under Irradiation with Ultrasound and/or Microwaves
  作者：Zhilin Wu、Bernd Ondruschka、Giancarlo Cravotto、Davide Garella、Jila Asgari

  DOI：10.1080/00397910802219387

  日期：2008.7.24

  Abstract The oxidation of primary aromatic amines, p-methylaniline, p-ethylaniline and p-chloroaniline to the corresponding azo- and azoxy-compounds has been observed in ultrasound and/or microwaves systems. The individual irradiation of microwaves and its simultaneous irradiation with ultrasound obviously elevate the conversion of amines, as compared with the individual irradiation of ultrasound and

  摘要 已经在超声和/或微波系统中观察到芳香伯胺、对甲基苯胺、对乙基苯胺和对氯苯胺氧化成相应的偶氮和偶氮化合物。与单独照射超声波和在普通水浴中加热相比，单独照射微波及其同时照射超声波明显提高了胺的转化率。然而，在二甲基甲酰胺 (DMF) 存在下，甲脒的形成导致对偶氮和偶氮产物的选择性较差。
• Synthesis of functionalised cyclic nitrones via regioselective and unusual [3 + 2] cycloadditions of α-nitrosostyrenes with 1,3-diazabuta-1,3-dienes and imines
  作者：Arun K. Sharma、Sujit N. Mazumdar、Mohinder P. Mahajan

  DOI：10.1039/a702254i

  日期：——

  The α-nitrosostyrenes 2, generated in situ from α-halogeno oximes, undergo regioselective [3 + 2] cycloaddition with 1,3-diazabuta-1,3-dienes 1 and 5 leading to the cyclic nitrones 3 and 6, respectively. Similarly, the cyclic nitrones 12 are also formed in reactions of 2 with the trisubstituted amidines 11. Thermolysis of the nitrones 3 and 12d–f gives imidazole derivatives 13. The nitrones 6, on the other hand, on thermolysis under similar conditions, give the amidine derivatives 17. Interestingly, the treatment of both 3 and 6 with NaBH4 in methanol and the reactions of 2 with N-arylbenzamidines also yield the imidazole derivatives 13.

  由 α-卤代肟原位生成的 α-亚硝基苯乙烯 2，与 1,3-diazabuta-1,3-二烯 1 和 5 进行区域选择性 [3+2] 环加成，生成环状硝酮 3 和 6，分别。类似地，环状硝酮 12 也在 2 与三取代脒 11 的反应中形成。硝酮 3 和 12d-f 的热解得到咪唑衍生物 13。另一方面，硝酮 6 在类似条件下热解，得到脒衍生物 17。有趣的是，用 NaBH4 在甲醇中处理 3 和 6，以及 2 与 N-芳基苯甲脒反应也得到咪唑衍生物 13。
• Prediction of tautomeric equilibria for N-arylamidines
  作者：Ewa D. Raczyńska

  DOI：10.1039/p29860001189

  日期：——

  The influence of substitution at amidine nitrogen atom on tautomeric equilibria and basicities of N-aryl-amidines is discussed. It is shown that tautomeric equilibrium constants (as pKT) can be correlated with σ∘ substituent constants, but measured pKam values of tautomeric mixture should obey a non-linear relation with σ∘ constants. The methods of prediction of pKT value are proposed, and applied

  讨论了nitrogen氮原子上的取代对N-芳基-的互变异构平衡和碱性的影响。结果表明，互变异构体平衡常数（如p K T）可以与σ∘取代基常数相关联，但是实测互变异构体混合物的p K a m值应服从与σ∘常数的非线性关系。提出了预测p K T值的方法，并将其应用于N-芳基-甲form和乙am。
• Hexamethyldisilazane-Mediated Amidination of Sulfonamides and Amines with Formamides
  作者：Yu-Chen Chou、Wei-Han Lin、Xiu-Yi Lin、Chin-Ling Kuo、Wan-Qin Zeng、I-Chung Lu、Chien-Fu Liang

  DOI：10.1021/acs.joc.2c01902

  日期：2022.11.18

  Hexamethyldisilazane was reacted with formamides to generate N,N-disubstituent formimidamide, after which a reaction with sulfonamides was induced to form sulfonylformamidines. This protocol can be applied for arylformamidine formation in which anilines are used as substrates under optimized conditions. The advantages of this method are high efficiency, structural diversity in products with good yields

  六甲基二硅氮烷与甲酰胺反应生成N , N-二取代基甲酰亚胺，然后与磺酰胺反应生成磺酰甲脒。该协议可应用于芳基甲脒形成，其中苯胺在优化条件下用作底物。该方法的优点是效率高，产品结构多样，产率高，适用于大规模操作。