5-甲氧基-3-甲基-1-苯基吡唑 | 27349-35-5

• 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-甲氧基-3-甲基-1-苯基吡唑
• 英文名称: 5-methoxy-3-methyl-1-phenyl-1H-pyrazole
• 英文别名: 5-Methoxy-3-methyl-1-phenyl-pyrazol；5-methoxy-3-methyl-1-phenylpyrazole；5-methoxy-3-methyl-1-phenyl-1H-pyrazole；5-Methoxy-3-methyl-1-phenyl-1H-pyrazol；1-Phenyl-3-methyl-5-methoxypyrazol；5-Methoxy-3-methyl-1-phenylpyrazol
• CAS: 27349-35-5
• 化学式: C₁₁H₁₂N₂O
• 分子量: 188.229
• InChiKey: MTLFMNFAALESGJ-UHFFFAOYSA-N

物化性质

• 沸点：
  95-100 °C(Press: 0.1 Torr)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-甲氧基-3-甲基-1-苯基吡唑 生成 安替比林
  参考文献：
  名称：

  Stolz, Journal fur praktische Chemie (Leipzig 1954), 1897, vol. <2> 55, p. 154

  摘要：

  DOI：
• 作为产物：
  描述：

  依达拉奉 以58%的产率得到
  参考文献：
  名称：

  Dehmlow Eckehard V., Klauck Robert, J. Chem. Res. Synop, (1994) N 11, S 448-449

  摘要：

  DOI：

文献信息

• A regioselective synthesis of 5-pyrazolones and pyrazoles from phosphazenes derived from hydrazines and acetylenic esters
  作者：Francisco Palacios、Ana M.Ochoa de Retana、Jaione Pagalday

  DOI：10.1016/s0040-4020(99)00890-x

  日期：1999.12

  Efficient and regioselective syntheses of 1-phenyl-5-pyrazolones substituted with a phosphoranylidene group in the 3-position and of 3-alkoxycarbonyl-5-methoxy-1-phenyl pyrazoles are described. The key step is the formation of functionalized hydrazones by [2+2] cycloaddition reaction of phosphazenes derived from hydrazines with acetylenic esters. Subsequent cyclization of these compounds with butyl

  描述了在3-位被磷亚烷基取代的1-苯基-5-吡唑啉酮和3-烷氧基羰基-5-甲氧基-1-苯基吡唑的高效和区域选择性合成。关键步骤是通过衍生自肼的磷腈与炔属酯的[2 + 2]环加成反应形成官能化的。随后用丁基锂将这些化合物环化，得到取代的5-吡唑啉酮，同时将它们与乙腈一起加热可形成区域选择性的3-烷氧基羰基-5-甲氧基-1-苯基吡唑。
• Rh(III)-Catalyzed C–H Amidation of Arenes with <i>N</i>-Methoxyamide as an Amidating Reagent
  作者：Guodong Ju、Guobao Li、Guanwen Qian、Jingyu Zhang、Yingsheng Zhao

  DOI：10.1021/acs.orglett.9b02625

  日期：2019.9.20

  The Rh(III)-catalyzed amidation of C(sp2)-H bonds has been reported by employing the N-methoxyamide as a novel amino source. An excellent level of functional group tolerance can be achieved when N-methoxyamide derivatives are used as the amidating reagents. Importantly, several known bioactive compounds such as Aminalon, Pregabalin, Gabapentin, and Probenecid can be transformed to effective amidating

  通过使用N-甲氧基酰胺作为新型氨基源，已经报道了Rh（III）催化的C（sp2）-H键的酰胺化反应。当使用N-甲氧基酰胺衍生物作为酰胺化试剂时，可以达到极好的官能团耐受性。重要的是，可以将几种已知的生物活性化合物（例如阿米那隆，普瑞巴林，加巴喷丁和丙磺舒）转化为有效的酰胺化试剂，以利于开发新的生物活性分子。
• Correlation of spectroscopically determined ligand donor strength and nucleophilicity of substituted pyrazoles
  作者：Jan Christopher Bernhammer、Han Vinh Huynh

  DOI：10.1039/c2dt30526g

  日期：——

  The relative ligand donor strengths of 10 pyrazole-derived ligands has been determined with great accuracy, making use of the interdependence between the donor strength of the co-ligand and the 13C NMR chemical shift of the iPr2-bimy carbene signal in trans-[PdBr2(iPr2-bimy)L] complexes (iPr2-bimy = 1,3-diisopropylbenzimidazolin-2-ylidene; L = pyrazole-derived ligand). Even subtle variations in the substitution pattern of the pyrazole backbone up to three bonds away from the coordinating nitrogen could be detected reliably using this methodology. Alkylation experiments conducted on the pyrazoles using electrophiles of varied reactivity (ethyl bromide, ethyl iodide, and trimethyloxonium tetrafluoroborate) served as a benchmark to rank the pyrazoles in three groups of gradually increasing nucleophilicity, which correlated well with their determined donor strength.

  通过利用协同配体中给体强度与反式-[PdBr2(iPr2-bimy)L]配合物中iPr2-bimy卡宾信号的13C NMR化学位移之间的相互依赖性，已精确测定了10种吡唑衍生的配体的相对供体强度（iPr2-bimy = 1,3-二异丙基苯并咪唑啉-2-亚基；L = 吡唑衍生配体）。即使吡唑骨架上与配位氮原子相隔三个键的取代模式的微妙变化，也能可靠地使用这种方法检测到。通过使用不同反应活性的亲电试剂（溴乙烷、碘乙烷和四氟硼酸三甲氧基甲基）对吡唑进行烷基化实验，将吡唑分为逐渐增强的亲核性的三个组，这与它们确定的供体强度高度相关。
• Synthesis, molecular properties prediction and anticancer, antioxidant evaluation of new edaravone derivatives
  作者：Naveen Polkam、Venkat Ragavan Ramaswamy、Parsharamulu Rayam、Tejeswara Rao Allaka、Hasitha Shilpa Anantaraju、Sriram Dharmarajan、Yogeeswari Perumal、Durgaiah Gandamalla、Narsimha Reddy Yellu、Sridhar Balasubramanian、Jaya Shree Anireddy

  DOI：10.1016/j.bmcl.2016.03.024

  日期：2016.5

  7c demonstrated good antioxidant activity with MIC values of 18.60, 16.27, 16.07 μg/mL respectively. Further the reported analogues were also tested on normal HEK293T cells and displayed low to good safer profiles. Derivatives 5l and 7c have come out to be safer potent anticancer, antioxidant agents. Additionally, the target products were subjected to their molecular properties prediction and drug likeness

  一系列新依达拉奉衍生物的3 - 7已被合成，其特征在于使用各种光谱技术和筛选它们体外抗癌，抗氧化活性。通过单晶X射线衍射进一步证实了5d的结构。在测试中，5l对PC3癌细胞表现出明显的活性。化合物5i，5l，7c显示出针对A549癌细胞的有效活性。产品5K，6，7C表现出良好的抗氧化活性，MIC值分别为18.60、16.27和16.07μg/ mL。此外，还对报道的类似物在正常的HEK293T细胞上进行了测试，并显示出从低到良好的安全特性。衍生物5l和7c已经成为更安全有效的抗癌剂，抗氧化剂。此外，通过使用Molinspiration和Osiris属性浏览器工具包，对目标产品进行了分子特性预测和药物相似性预测。他们都没有违反Lipinski的界限，将标题化合物归类为潜在的抗癌剂和抗氧化剂。
• Alkylation of Pyrazolones via the Mitsunobu Reaction
  作者：Wolfgang Holzer、Brigitte Plagens、Karin Lorenz

  DOI：10.3987/com-96-7657

  日期：——

  The reaction of 3-methyl-1-phenyl-2-pyrazolin-5-one and 4-acyl derivatives thereof (R-4 = COPh, 2-thienoyl, COCH2CH2Ph, COCH=CHPh) with various alcohols under 'Mitsunobu'-conditions was studied. In many cases selective O-alkylation could be achieved.