ethylenedihydrazine | 6068-98-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: ethylenedihydrazine
• 英文别名: ethylene bis(hydrazine)；1,2-Hydrazino-ethan；1,2-Ethylendihydrazin；1,1'-Aethylendihydrazin；N,N''-ethanediyldi-hydrazine；N,N''-Aethandiyldi-hydrazin；2-Hydrazinoethyl-hydrazin；1,2-Dihydrazino-aethan；2-hydrazinylethylhydrazine
• CAS: 6068-98-0
• 化学式: C₂H₁₀N₄
• mdl: MFCD01365839
• 分子量: 90.1282
• InChiKey: MNCTVKQVIMVWOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  6
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  76.1
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethylenedihydrazine 在 dinitraminic acid 作用下， 以 乙醚 、 乙醇 为溶剂， 以70%的产率得到
  参考文献：
  名称：

  Dinitramide and its salts

  摘要：

  The methods for preparation and the properties of dinitramide salts with ammonia, hydrazine, hydroxylamine, formamidine, their alkylated and aminated derivatives, etc. are described.

  DOI：

  10.1007/bf00696969
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 生成 ethylenedihydrazine
  参考文献：
  名称：

  杂环系列中的药用化学研究。18.沟通。关于聚亚甲基双亚砜和聚亚甲基双肼

  摘要：

  描述了N，N′-亚乙基-，N，N′-四亚甲基，N，N′-六亚甲基和C，C′-二甲基-N，N′-亚乙基-双-sydnon的合成。将获得的一些双双sydnones转化为C，C'-二卤代-N，N'-聚亚甲基双双sydnones。通过用酸分解双sydnones，获得相应的脂族双肼，其与苯甲醛和邻苯二甲醛反应。

  DOI：

  10.1002/hlca.19570400406

文献信息

• New Hydrazinium Salts of 5,5'-Azotetrazolate
  作者：Anton Hammerl、Gerhard Holl、M. Kaiser、Thomas M. Klapötke、Peter Mayer、Heinrich Nöth、Holger Piotrowski、Max Suter

  DOI：10.1515/znb-2001-0902

  日期：2001.9.1

  Salts of the 5,5′-azotetrazolate dianion with several different hydrazinium cations were pre­ pared. The compounds were characterized by elemental analysis, vibrational spectroscopy (IR, Raman) and multinuclear NMR spectroscopy (¹H, ¹³C, ¹⁴ N). The crystal structures of the di-tert-butylhydrazinium, the ethylenedihydrazinium, the diguanidinium and the bis-triamino-guanidinium azotetrazolate were determined. The thermal, shock and friction sensitivities of all compounds were investigated and their explosion products were analysed. For the 5,5′-azotetr-azolate dianion the structure was calculated with density functional theory (B3-LYP). An NBO analysis was performed for the 5,5′-azotetrazolate dianion in order to understand the charge distribution of the dianion.

  用几种不同的双肼阳离子制备了5,5′-偶氮四唑二阴离子的盐。通过元素分析、振动光谱（红外、拉曼）和多核NMR光谱（1H、13C、14N）对这些化合物进行了表征。确定了二叔丁基双肼阳离子、乙二双肼阳离子、二胍阳离子和双三氨基胍阳离子偶氮四唑的晶体结构。研究了所有化合物的热、冲击和摩擦敏感性，并分析了其爆炸产物。对5,5′-偶氮四唑二阴离子的结构进行了密度泛函理论（B3-LYP）计算。为了了解二阴离子的电荷分布，对5,5′-偶氮四唑二阴离子进行了NBO分析。

• Synthesis and Biological Activity of Aminoguanidine and Diaminoguanidine Analogues of the Antidiabetic/Antiobesity Agent 3-Guanidinopropionic Acid
  作者：Valerie A. Vaillancourt、Scott D. Larsen、Steven P. Tanis、Jeffery E. Burr、Mark A. Connell、Michele M. Cudahy、Bruce R. Evans、Peter V. Fisher、Paul D. May、Martin D. Meglasson、Deborah D. Robinson、F. Craig Stevens、John A. Tucker、Thomas J. Vidmar、Jen H. Yu

  DOI：10.1021/jm000094n

  日期：2001.4.1

  3-Guanidinopropionic acid (1) has been demonstrated both to improve insulin sensitivity and to promote weight loss selectively from adipose tissue in animal models of non-insulin-dependent diabetes mellitus (NIDDM). However, 1 has also been shown to be a substrate for both the creatine transporter and creatine kinase, leading to marked accumulation in muscle tissue as the corresponding N-phosphate. The corresponding aminoguanidine analogue 2 was recently discovered to retain the antidiabetic activity of 1 while being markedly less susceptible to creatine-like metabolism, suggesting that it should have less potential to accumulate in muscle. Further structural modification of 2 was undertaken to investigate whether the antidiabetic potency could be augmented while maintaining resistance to creatine-like metabolism. Modifications such as a-alkylation, homologation, and bioisosteric replacement of the aminoguanidine all were detrimental to antidiabetic activity. However, the simple regioisomeric aminoguanidinoacetic acid 9 and diaminoguanidinoacetic acid-analogue 7 were found to be equipotent to 2, leading eventually to the discovery of the significantly more potent diaminoguanidinoacetic acid regioisomers 52 and 53. Further attempts to modify the more active template represented by 52 led only to reductions in; antidiabetic activity. Each of the new active analogues displayed the same resistance to creatine-like metabolism as 2. Further testing of 7, 9, and 53 in obese diabetic ob;lob mice confirmed that weight loss is induced selectively from adipose tissue, similar to the lead 1. Administration of 53 to insulin-resistant rhesus monkeys led to reductions in both fasting and post-prandial plasma glucose levels with concomitant reductions in plasma insulin levels, suggesting that the compound improved the action of endogenous insulin. Compounds 7 and 53 were selected for further preclinical development.
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