N-乙基-N'-羟基脲 | 5710-11-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 中文名称: N-乙基-N'-羟基脲
• 英文名称: N-ethyl-N'-hydroxyurea
• 英文别名: 3-ethyl-hydroxyurea；N-ethyl-N'-hydroxy-urea；N-Aethyl-N'-hydroxy-harnstoff；Kohlensaeure-aethylamid-hydroxylamid；N-Aethyl-N'-hydroxy-harnstoff；N-Ethylcarbamoyl-hydroxylamin；1-Ethyl-3-hydroxyurea
• CAS: 5710-11-2
• 化学式: C₃H₈N₂O₂
• mdl: MFCD01676126
• 分子量: 104.109
• InChiKey: PPWNKYXWTZJASD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  61.4
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-乙基-N'-羟基脲 在 氯磺酸 、 硫酸 作用下， 生成 N-Aethyl-N'-hydroxyharnstoff-O-sulfonsaeure
  参考文献：
  名称：

  Ohme,R.; Preuschhof,H., Journal fur praktische Chemie (Leipzig 1954), 1970, vol. 312, p. 349 - 358

  摘要：

  DOI：
• 作为产物：
  描述：

  异氰酸乙酯 在 羟胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 N-乙基-N'-羟基脲
  参考文献：
  名称：

  3-羟基缩二脲的合成研究 羟胺衍生物的第 22 次通讯

  摘要：

  2mol异氰酸苯酯与1mol羟胺的反应产物证明了1,5-二苯基-3-羟基缩二脲的结构；该化合物的O-取代衍生物是首次产生。根据反应条件，羟胺与脂肪族异氰酸酯和异氰酸环己酯反应生成羟基脲、3-羟基双脲和 N, N, O-三（氨基甲酰基）-羟胺。

  DOI：

  10.1002/ardp.19652981210

文献信息

• Electrochemical acylation and alkylaminocarbonylation of amines and alcohols
  作者：Masaichiro Masui、Shigeko Alcohols

  DOI：10.1016/s0040-4039(00)88435-x

  日期：1982.1

  Electrochemical acylation and ethylaminocarbonylation of amines and alcohols are performed by anodic oxidation of the hydroxamic acids and N-ethyl-N′hydroxyurea, respectively, in acetonitrile at a glassy-carbon electrode.

  胺和醇的电化学酰化和乙基氨基羰基化反应分别通过在玻璃碳电极上的乙腈中将异羟肟酸和N-乙基-N'羟基脲进行阳极氧化来实现。
• N-Substituted Hydroxyureas as Urease Inhibitors.
  作者：Shinichi Uesato、Yuichiro Hashimoto、Masaru Nishino、Yasuo Nagaoka、Hiroshi Kuwajima

  DOI：10.1248/cpb.50.1280

  日期：——

  In order to seek a urease inhibitor more potent than hydroxyurea (1), its alkyl- or phenyl-substituted derivatives were synthesized and evaluated for their effect on the jack bean urease. Of 16 compounds tested, m-methyl- (10) and m-methoxy-phenyl substituted hydroxyurea (13) showed the most potent inhibitory activities against the enzyme.

  为了寻找比羟基脲（1）更有效的脲酶抑制剂，我们合成了其烷基或苯基取代衍生物，并评估了它们对胡豆脲酶的影响。在测试的 16 种化合物中，间甲基（10）和间甲氧基苯基取代的羟基脲（13）对该酶的抑制活性最强。
• Oxidation of hydroxylamine derivatives. Part 5. Anodic oxidation of N-hydroxy- and N-alkoxy-ureas
  作者：Shigeko Ozaki、Masaichiro Masui

  DOI：10.1039/p29800001022

  日期：——

  The anodic oxidation of the ureas EtNH·CO·NR1OR2(1)–(5) has been studied by cyclic voltammetry and controlled potential electrolysis in acetonitrile at a glassy carbon electrode. The products of oxidation suggest that (1)–(3) result in cleavage between the carbon of the ethylaminocarbonyl group and the nitrogen of the hydroxyamino-group. Part of the intermediate radical of (3) undergoes disproportionation

  尿素EtNH·CO·NR 1 OR 2（1）–（5）的阳极氧化已通过循环伏安法和在玻璃碳电极上乙腈中受控电势电解的方法进行了研究。氧化产物表明（1）–（3）导致乙基氨基羰基碳与羟基氨基氮之间的裂解。（3）的部分中间自由基发生歧化而不是碳氮键断裂。在（4）和（5）的情况下，在（1）-（3）中观察到的碳-氮键的裂解是主要的反应途径，但是中间体发生N-N偶联并随后发生分子内反应的可能性重排不能忽略。氧化在分裂和未分裂的细胞中进行。
• N-substituted N'-hydroxythioureas
  作者：Gil Clifton、Sarah R. Bryant、Charles G. Skinner

  DOI：10.1021/jm00297a009

  日期：1970.5
• Synthesis of 9-(2-β-C-methyl-β-d-ribofuranosyl)-6-substituted purine derivatives as inhibitors of HCV RNA replication
  作者：Yili Ding、Jean-Luc Girardet、Zhi Hong、Vicky C.H. Lai、Haoyun An、Yung-hyo Koh、Stephanie Z. Shaw、Weidong Zhong

  DOI：10.1016/j.bmcl.2004.11.020

  日期：2005.2

  A series of 9-(2'-beta-C-methyl-p-D-ribofuranosyl)-6-substituted purine derivatives were synthesized as potential inhibitors of HCV RNA replication. Their inhibitory activities in a cell based HCV replicon assay were reported. A prodrug approach was used to further improve the potency of these compounds by increasing the intracellular levels of 5'-monophosphate metabolites. These nucleotide prodrugs showed much improved inhibitory activities of HCV RNA replication. (C) 2004 Elsevier Ltd. All rights reserved.