N-乙基胍 | 503-69-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-乙基胍
• 中文别名: 1-乙基胍
• 英文名称: ethyl guanidine
• 英文别名: N-ethyl-guanidine；N-Ethylguanidine；2-ethylguanidine
• CAS: 503-69-5
• 化学式: C₃H₉N₃
• 分子量: 87.1246
• InChiKey: KEWLVUBYGUZFKX-UHFFFAOYSA-N

物化性质

• 沸点：
  121.1±23.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 海关编码：
  2925290090

反应信息

• 作为反应物：
  描述：

  N-乙基胍 生成 N-ethyl-N',N''-dibenzoyl-guanidine
  参考文献：
  名称：

  Olin; Dains, Journal of the American Chemical Society, 1930, vol. 52, p. 3323

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氨 、 水 作用下， 生成 N-乙基胍
  参考文献：
  名称：

  Schenck; Kirchhof, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1926, vol. 154, p. 300

  摘要：

  DOI：

文献信息

• SYNTHESES OF SUBSTITUTED GUANIDINES
  作者：Paul E. Gagnon、Jean L. Boivin、Joseph Zauhar

  DOI：10.1139/v58-211

  日期：1958.10.1

  Ethyl-, propyl-, and benzyl-guanidine nitrates were prepared from amine nitrates and calcium cyanamide or dicyandiamide. Carboxyalkylguanidines were made by condensing the corresponding amino acids with guanidine carbonate in aqueous medium. All the guanidine nitrates, except the benzyl derivative, were converted into the corresponding nitroguanidines by treatment with concentrated sulphuric acid. Esters and metal salts of 1-(α-carboxyalkyl)-2-nitroguanidines were also prepared.

  乙基、丙基和苄基胍硝酸盐是由胺硝酸盐和氰胺钙或二氰胺制备而成的。羧基胍胺是通过在水介质中将相应的氨基酸与碳酸胍胺缩合而成的。除苄基衍生物外，所有的胍硝酸盐都经过浓硫酸处理转化为相应的硝基胍。还制备了1-(α-羧基烷基)-2-硝基胍的酯和金属盐。
• Visible Light-Induced Aerobic Epoxidation of α,β-Unsaturated Ketones Mediated by Amidines
  作者：Yufeng Wu、Guangli Zhou、Qingwei Meng、Xiaofei Tang、Guangzhi Liu、Hang Yin、Jingnan Zhao、Fan Yang、Zongyi Yu、Yi Luo

  DOI：10.1021/acs.joc.8b01710

  日期：2018.11.2

  photoepoxidation of α,β-unsaturated ketones driven by visible light in the presence of tetramethylguanidine (3b), tetraphenylporphine (H2TPP), and molecular oxygen under mild conditions was revealed. The corresponding α,β-epoxy ketones were obtained in yields of up to 94% in 96 h. The reaction time was shortened to 4.6 h by flow synthesis. The mechanism related to singlet oxygen was supported by experiments

  在温和条件下，在四甲基胍（3b），四苯基卟啉（H 2 TPP）和分子氧的存在下，可见光驱动α，β-不饱和酮的有氧光环氧化。在96小时内以高达94％的产率获得了相应的α，β-环氧酮。通过流动合成将反应时间缩短至4.6小时。实验和密度泛函理论（DFT）计算支持了与单线态氧有关的机理。
• Chitosan: an efficient promoter for the synthesis of 2-aminopyrimidine-5-carbonitrile derivatives in solvent free conditions
  作者：I. R. Siddiqui、Pragati Rai、Rahila、Anushree Srivastava

  DOI：10.1039/c4nj00199k

  日期：——

  Reusable chitosan without any post-modification, with active –NH2 and –OH groups, was found to be a highly efficient and renewable heterogeneous catalyst for the rapid and convenient synthesis of 2-aminopyrimidine-5-carbonitrile derivatives from guanidines, aldehydes and cyanoketones, under mild reaction conditions at 85 °C in good yields. Undoubtedly this methodology gives a facile and straightforward pathway to construct 2-aminopyrimidine-5-carbonitrile derivatives in an eco-friendly fashion.

  未经任何后修饰的可重复使用的壳聚糖，因其含有活性-NH2和-OH基团，被发现是一种高效且可再生的非均相催化剂，能够在温和反应条件下（85°C）以良好产率快速便捷地合成2-氨基嘧啶-5-腈衍生物，所用原料为胍、醛和氰基酮。毫无疑问，这一方法为环保地构建2-氨基嘧啶-5-腈衍生物提供了一个简便直接的途径。
• One-pot NHC-assisted access to 2,3-dihydropyrimido[4,5-d]pyrimidin-4(1H)-ones
  作者：Mingxing Liu、Jiarong Li、Shu Chen、Danfei Huang、Hongxin Chai、Qi Zhang、Daxin Shi

  DOI：10.1039/c4ra05346j

  日期：——

  2-(ethoxymethylene)malononitrile, guanidines (or amidines) and ketones (or aldehydes) has been developed. This highly efficient method includes a series of conversions such as Michael addition, cyclisation, isomerization, aromatization, then nucleophilic attack and Dimroth rearrangement. And it avoids complicated reagents and multiple steps.

  由N-杂环卡宾辅助的一锅反应，由2-（乙氧基亚甲基）丙二腈，胍（或am）合成2，3-二氢嘧啶并[4,5- d ]嘧啶-4（1 H）-酮（或醛）已经开发出来。这种高效的方法包括一系列转化，例如迈克尔加成，环化，异构化，芳构化，亲核攻击和Dimroth重排。而且避免了复杂的试剂和多个步骤。
• Synthesis of novel strobilurin–pyrimidine derivatives and their antiproliferative activity against human cancer cell lines
  作者：Baoshan Chai、Shuyang Wang、Wenquan Yu、Huichao Li、Chuanjun Song、Ying Xu、Changling Liu、Junbiao Chang

  DOI：10.1016/j.bmcl.2013.04.045

  日期：2013.6

  based on the structures of our previously discovered antiproliferative compounds I and II. Biological evaluation with two human cancer cell lines (A549 and HL60) showed that most of these compounds possessed moderate to potent antiproliferative activity. Two potent candidates (8f, IC50 = 2.2 nM and 11d, IC50 = 3.4 nM) were identified with nanomolar activity against leukemia cancer cell line HL60 for

  根据我们先前发现的抗增殖化合物I和II的结构，设计并合成了一系列新的strobilurin-pyrimidine类似物。用两种人类癌细胞系（A549和HL60）进行生物学评估表明，这些化合物大多数都具有中度到强效的抗增殖活性。 鉴定出两个有效候选物（8f，IC 50  = 2.2 nM和11d，IC 50 = 3.4 nM），它们具有针对白血病癌细胞系HL60的纳摩尔活性，可用于进一步开发。与母体化合物I和II相比，该活性提高了1000到2500倍并且比化疗药物阿霉素好20到30倍。目前的工作为进一步开发这些嗜球果伞素-嘧啶类似物作为潜在的抗白血病药物提供了强有力的动力。