5-肼基-2-苯基-1,3-恶唑-4-甲腈 | 314748-14-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5-肼基-2-苯基-1,3-恶唑-4-甲腈
• 英文名称: 5-hydrazino-2-phenyl-1,3-oxazole-4-carbonitrile
• 英文别名: 2-phenyl-4-cyano-5-hydrazino-1,3-oxazole；2-phenyl-4-cyano-5-hydrazinooxazole；5-Hydrazinyl-2-phenyl-1,3-oxazole-4-carbonitrile
• CAS: 314748-14-6
• 化学式: C₁₀H₈N₄O
• mdl: MFCD01409298
• 分子量: 200.2
• InChiKey: QIRKRPUTAYTVGW-UHFFFAOYSA-N

物化性质

• 沸点：
  450.5±55.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.9
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-肼基-2-苯基-1,3-恶唑-4-甲腈 在 三氟乙酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.42h， 生成 N-(5-(5-amino-2-phenyloxazol-4-yl)-1,3,4-thiadiazol-2-yl)acetamide
  参考文献：
  名称：

  Reaction of 2-aryl(methyl)-4-cyano-5-hydrazino-1,3-oxazoles with aryl Isothiocyanates

  摘要：

  Accessible 2-aryl(methyl)-4-cyano-5-hydrazino-1,3-oxazoles add to aryl isothiocyanates. The resulting products undergo recyclization to form new 1,3,4-thiadiazole derivatives hearing an acylamino group on C-2 and an (acylamino)(cyano)methyl group on C-5. The structure of the new compounds was proved by their IR and H-1 NMR spectra, as well as by conversion in other 1,3,4-thiadiazole derivatives.

  DOI：

  10.1134/s1070363207050209
• 作为产物：
  描述：

  2-benzoylamino-3,3-dichloroacrylonitrile 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 5-肼基-2-苯基-1,3-恶唑-4-甲腈
  参考文献：
  名称：

  从 2-酰基氨基-3,3-二氯丙烯腈开始合成新的 1,3,4-噻二唑衍生物

  摘要：

  可用的 2-acylamino-3,3-dichloroacrylonitriles，当用肼水合物处理时，可提供 2-烷基-或 2-芳基-5-肼基-1,3-恶唑-4-腈，可轻松添加烷基或芳基异硫氰酸酯和加合物形成循环加热。最后，合成产生 5-烷基（芳基）氨基-1,3,4-噻二唑-2-基（酰基氨基）乙腈或其进一步环化的产物，2-(5-氨基-1,3-恶唑- 2-基)-1,3,4-噻二唑衍生物。新型取代的 1,3,4-噻二唑的结构通过光谱和 X 射线衍射方法得到证实。© 2004 Wiley Periodicals, Inc. 杂原子化学 15:454–458, 2004; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20041

  DOI：

  10.1002/hc.20041

文献信息

• Transformations of Acylation Products of Functionally 4-Substituted 2-Alkyl(aryl)-5-hydrazino-1,3-oxazoles into 1,3,4-Oxadiazole Derivatives
  作者：A. V. Golovchenko、S. G. Pil’o、V. S. Brovarets、A. N. Chernega、B. S. Drach

  DOI：10.1007/s11176-005-0244-8

  日期：2005.3

  Acylation products of 2-aryl-5-hydrazino-4-X-1,3-oxazoles [X = C(O)OAlk, P(O)(OAlk)2], when heated in acetic acid or ethanol, undergo recyclization and transform into the derivatives of 1,3,4-oxadiazol-2-ylglycine or its phosphonyl analog. A similar rearrangement also occurs in the reactions of 2-alkyl(aryl)-5-hydrazino-1,3-oxazole-4-carbonitriles with carboxylic acid chlorides in pyridine, but it is accompanied by additional cyclization involving the amide residue and nitrile group, yielding 2-(5-amino-1,3-oxazol-4-yl)-1,3,4-oxadiazole derivatives.

  2-芳基-5-肼基-4-X-1,3-噁唑的酰化产物 [X = C(O)OAlk, P(O)(OAlk)2] 在加热于醋酸或乙醇时，发生重环化，转化为 1,3,4-噁二唑-2-基甘氨酸或其磷酸酯类似物的衍生物。在与吡啶中的羧酸氯化物反应时，2-烷基（芳基）-5-肼基-1,3-噁唑-4-腈也发生类似的重排，但伴随有额外的环化，涉及酰胺残基和腈基，生成 2-(5-氨基-1,3-噁唑-4-基)-1,3,4-噁二唑衍生物。
• Peculiar reaction of N2-acyl derivatives of 2-aryl-5-hydrazino-1,3-oxazole-4-carbonitriles with the lawesson reagent
  作者：Oleg V. Shablykin、Vladimir S. Brovarets、Eduard B. Rusanov、Boris S. Drach

  DOI：10.1002/hc.20413

  日期：2007.11

  Easily accessible N2-acyl derivatives of 2-aryl-5-hydrazino-1,3-oxazole-4-carbonitriles react peculiarly with the Lawesson reagent. In addition to thionation, the reaction involves a recyclization to afford new substituted 2-(5-amino-1,3-thiazol-4-yl)-1,3,4-thiadiazoles. Their structure is corroborated spectroscopically and by the X-ray diffraction method. © 2007 Wiley Periodicals, Inc. Heteroatom

  2-aryl-5-hydrazino-1,3-oxazole-4-carbonitriles 的容易获得的 N2-酰基衍生物与 Lawesson 试剂发生特殊反应。除了硫化作用外，该反应还包括再循环以提供新的取代的 2-(5-amino-1,3-thiazol-4-yl)-1,3,4-thiadiazoles。它们的结构通过光谱和 X 射线衍射方法得到证实。© 2007 Wiley Periodicals, Inc. 杂原子化学 18:782–785, 2007; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20413
• New transformations of 5-Hydrazino-2-phenyl-1,3-oxazole-4-carbonitrile
  作者：O. V. Shablykin、V. S. Brovarets、B. S. Drach

  DOI：10.1134/s1070363207050210

  日期：2007.5

  Treatment of 5-hydrazino-2-phenyl-1,3-oxazole-4-carbonitrile with acetylacetone lead to the formation of a substituted pyrazole residue on C-5, which enhanced the electrophilicity of the cyano group in position 4 so that it became capable of reacting with hydrogen sulfide, sodium azide, and hydroxylamine. As a result, the corresponding azole fragments were introduced into position 4 of the 5-(1H-pyrazol-1-yl)-1,3-oxazole system.
• Transformation of 2-acylamino-3,3-dichloroacrylonitriles into substituted 4-amino[1,3]oxazolo[4,5-e]pyrazolo-[1,5-a]pyrimidines
  作者：O. V. Shablykin、V. S. Brovarets

  DOI：10.1134/s1070363207080361

  日期：2007.8
• ——
  作者：S. G. Pil'o、V. S. Brovarets、T. K. Vinogradova、A. N. Chernega、B. S. Drach

  DOI：10.1023/a:1012315925344

  日期：——

  The available 2-benzoylamino-3,3-dichloroacrylonitrile and its analogs when treated with excess hydrazine hydrate convert to 2-aryl-4-cyano-5-hydrazinooxazoles. The products are fairly stable in usual conditions but undergo recyclization on heating in acetic acid to give previously unknown derivatives of 2-methyl-1,3,4-oxadiazole with a 5-acylamino(carbamoyl)methyl substituent, whose structure was established by spectroscopy and X-ray diffraction. An important role in this complex transformation is probably played by prototropic forms of 4-cyano-5-hydrazinooxazoles, viz. hydrazones of substituted 2-oxazolin-5-ones which are not aromatic and thus can be cleaved with acetic acid and then recyclize.