methyl 5-hydrazino-2-phenyl-1,3-oxazole-4-carboxylate | 663177-19-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 5-hydrazino-2-phenyl-1,3-oxazole-4-carboxylate
• 英文别名: Methyl 5-hydrazinyl-2-phenyl-1,3-oxazole-4-carboxylate
• CAS: 663177-19-3
• 化学式: C₁₁H₁₁N₃O₃
• 分子量: 233.227
• InChiKey: IQEGWPBPROBARH-UHFFFAOYSA-N

物化性质

• 熔点：
  190-191 °C(Solv: methanol (67-56-1))
• 沸点：
  435.5±55.0 °C(Predicted)
• 密度：
  1.330±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  90.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 5-hydrazino-2-phenyl-1,3-oxazole-4-carboxylate 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 88.0h， 生成 5-anilino-2-(benzoylamino)methyl-1,3,4-thiadiazole
  参考文献：
  名称：

  A Facile Synthesis of Derivatives of (1,3,4-Thiadiazol-2-yl)glycine and Its Phosphonyl Analogue

  摘要：

  由 4-功能取代的 2-芳基-5-肼基-1,3-恶唑和芳基异硫氰酸酯形成的加合物在加热时会发生再循环，生成迄今未知的 (1,3,4-thiadiazol-2-yl)glycine 衍生物及其膦酰类似物。

  DOI：

  10.1055/s-2003-42458
• 作为产物：
  描述：

  methyl ester of 3,3-dichloro-2-benzoylaminoacrylic acid 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以85%的产率得到methyl 5-hydrazino-2-phenyl-1,3-oxazole-4-carboxylate
  参考文献：
  名称：

  A Facile Synthesis of Derivatives of (1,3,4-Thiadiazol-2-yl)glycine and Its Phosphonyl Analogue

  摘要：

  由 4-功能取代的 2-芳基-5-肼基-1,3-恶唑和芳基异硫氰酸酯形成的加合物在加热时会发生再循环，生成迄今未知的 (1,3,4-thiadiazol-2-yl)glycine 衍生物及其膦酰类似物。

  DOI：

  10.1055/s-2003-42458

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。
• Recyclization of Products Formed by Addition of 5-Hydrazino-2-phenyl-1,3-oxazoles Functionally Substituted in 4-Position to Aryl Isothiocyanates
  作者：A. V. Golovchenko、S. G. Pil'o、V. S. Brovarets、B. S. Drach

  DOI：10.1023/b:rugc.0000018668.00291.da

  日期：2003.11

  between alternative structures IV and V was based on the results of a single crystal X-ray diffraction study of the product formed by the reaction of Ia with p-tolyl isothiocyanate. This compound was unambiguously identified as the 1,3,4thiadiazole derivative. Possible applications of this recyclization, resembling formation of related 1,3,4oxadiazole derivatives [1, 3], will be considered in subsequent papers

  质子平衡 II III 很可能发生，随后的再循环 III IV 显然是由于不稳定的 5-亚氨基-2-恶唑啉衍生物很容易转化为具有明显芳香性的取代的 1,3,4-噻二唑。H NMR光谱与这种特殊反应的最终产物的建议结构一致；然而，替代结构 IV 和 V 之间的最终选择是基于对 Ia 与对甲苯基异硫氰酸酯反应形成的产物的单晶 X 射线衍射研究的结果。该化合物被明确确定为 1,3,4 噻二唑衍生物。这种再循环的可能应用，类似于形成相关的 1,3,4 恶二唑衍生物 [1, 3]，将在后续论文中考虑。
• 2-aryl-5-arylsulfanyl-1,3-oxazole-4-carboxylic acids and their derivatives
  作者：S. G. Pil’o、V. M. Prokopenko、V. S. Brovarets、B. S. Drach

  DOI：10.1134/s1070363210070212

  日期：2010.7

  A convenient preparative procedure has been developed for the synthesis of previously unknown 2-aryl- 5-arylsulfanyl-1,3-oxazole-4-carboxylic acids and their functional derivatives from accessible multicenter substrates of the general formula Cl(2)C=C(NHCOR)C(O)OMe. The products turned out to be suitable for various subsequent transformations. Some oxazole-4-carboxylic acid hydrazide derivatives containing a substituted oxazol-5-yl fragment at the N(2) atom in the hydrazine moiety underwent recyclization on heating in acetic acid; as a result, one oxazole ring was converted into 1,3,4-oxadiazole.
• A Facile Synthesis of Derivatives of (1,3,4-Thiadiazol-2-yl)glycine and Its Phosphonyl Analogue
  作者：Vladimir S. Brovarets、Aleksandr V. Golovchenko、Stepan G. Pilyo、Alexander N. Chernega、Boris S. Drach

  DOI：10.1055/s-2003-42458

  日期：——

  The adducts formed by 4-functionally-substituted 2-aryl-5-hydrazino-1,3-oxazoles and aryl isothiocyanates recyclize on heating to produce the hitherto unknown derivatives of (1,3,4-thiadiazol-2-yl)glycine and its phosphonyl analogue.

  由 4-功能取代的 2-芳基-5-肼基-1,3-恶唑和芳基异硫氰酸酯形成的加合物在加热时会发生再循环，生成迄今未知的 (1,3,4-thiadiazol-2-yl)glycine 衍生物及其膦酰类似物。
• Synthesis and transformations of derivatives of 2-aryl-5-(3,5-dimethyl-1H-pyrazol-1-yl)-1,3-oxazole-4-carboxylic acid
  作者：V. M. Prokopenko、S. G. Pil’o、A. N. Vasilenko、V. S. Brovarets

  DOI：10.1134/s1070363210110216

  日期：2010.11

  On the basis of methyl esters of 2-aryl-5-hydrazino-1,3-oxazole-4-carboxylic acids the earlier unknown methyl esters of 2-aryl-5-(3,5-dimethyl-1H-pyrazol-1-yl)-1,3-oxazole-4-carboxylic acids as well as their functional derivatives were synthesized. The latter were used for further transformations, in particular, for introducing the residues of highly basic aliphatic amines into the 5 position of oxazole, and the oxazol-2-yl moiety into the 4 position of the oxazole ring.