3-(4-甲氧基苯基)丙酰肼 | 121670-33-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-(4-甲氧基苯基)丙酰肼
• 中文别名: 3-(4-甲氧苯基)丙酰肼；3-(4-甲氧苯基)丙烷肼
• 英文名称: 3-(4-methoxyphenyl)propionic acid hydrazide
• 英文别名: 3-(4-methoxyphenyl)propanoylhydrazine；3-(4-methoxyphenyl)propanehydrazide；3-(4-methoxy-phenyl)-propionic acid hydrazide；3-(4-Methoxy-phenyl)-propionsaeure-hydrazid；3-(4-Methoxyphenyl)propanohydrazide
• CAS: 121670-33-5
• 化学式: C₁₀H₁₄N₂O₂
• mdl: MFCD00463001
• 分子量: 194.233
• InChiKey: BFZQOADVWOLSQE-UHFFFAOYSA-N

物化性质

• 沸点：
  412.2±28.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  3-(4-甲氧基苯基)丙酰肼 在 三氟乙酸吡啶 、 对甲苯磺酸 作用下， 反应 0.25h， 生成 3-[2-(4-methoxyphenyl)ethyl]-4-phenyl-4H-1,2,4-triazole
  参考文献：
  名称：

  Tunable protic ionic liquids as solvent-catalysts for improved synthesis of multiply substituted 1,2,4-triazoles from oxadiazoles and organoamines

  摘要：

  More than green alternatives to traditional volatile molecular organic solvents, protic ionic liquids as dual solvent-catalysts have been successfully used to promote reactions of organoamines with oxadiazoles to afford sterically hindered 1,2,4-triazoles. Among the tested protic ionic liquids, pyridinium trifluoroacetate and acetate showed the highest efficiency for the reactions of arylamines and alkylamines, respectively, indicating that tunable catalysis could be readily effected with protic ionic liquid solvent-catalysts by simply tuning their cation and anion counterparts. A general and efficient approach has been developed for synthesis of multiply substituted 1,2,4-triazoles based on the tunable protic ionic liquid solvent-catalyst systems. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.114
• 作为产物：
  描述：

  3-(4-甲氧基苯基)丙酸 在 硫酸 、 一水合肼 作用下， 以 甲醇 为溶剂， 生成 3-(4-甲氧基苯基)丙酰肼
  参考文献：
  名称：

  某些4-氨基-5-芳基-3H-1,2,4-三唑-3-硫酮及其3,6-二取代的1,2,4-三唑[3,4]的合成，脲酶抑制，抗氧化和抗菌研究-b] 1,3,4-噻二唑衍生物

  摘要：

  通过将肼基碳二硫代钾盐在水合肼的稀水溶液中回流，合成了一系列新的带有各种甲氧基苄基和甲氧基苯乙基的4-氨基-5-芳基-3H-1,2,4-三唑-3-硫酮。这些盐是通过酰肼与二硫化碳在甲醇氢氧化钾溶液中于0-5°C反应形成的。将4-氨基-5-芳基-3H-1,2,4-三唑-3-硫酮与不同的取代芳族酸缩合，生成3,6-二取代-1,2,4-三唑[3,4-b] 1,3,4-噻二唑。合成的化合物的结构通过红外（IR），1H和13C核磁共振（NMR），元素分析和质谱（MS）研究进行了表征。筛选所有合成的化合物的脲酶抑制作用，抗氧化剂和抗菌活性。一些化合物显示出优异的脲酶抑制活性，超过了标准药物。其他人表现出强大的抗氧化活性。与标准药物相比，所有化合物均显示出显着的抗菌活性。

  DOI：

  10.1590/s0103-50532012000500010

文献信息

• Intramolecular addition of acyldiazenecarboxylates onto double bonds in the synthesis of heterocycles
  作者：José V. Prata、Dina-Telma S. Clemente、Sundaresan Prabhakar、Ana M. Lobo、Isabel Mourato (in part)、Paula S. Branco (in part)

  DOI：10.1039/b110414d

  日期：2002.2.6

  Appropriate aryl-substituted unsymmetrical azodicarbonyl compounds, generated from bishydrazides by oxidation, undergo intramolecular cyclisations to furnish a variety of useful heterocycles such as N-substituted oxindoles, carbostyrils, benzazepinones, benzazocinones, benzimidazolones, benzoxazinones and pyrazolones in varying degrees of efficiency. Methods are described to remove the N-acyl groups from the heteroaromatic compounds. Under mildly acidic conditions where equal opportunities are available for an ipso or a normal cyclisation it is the former process that occurs preferentially. Evidence is presented in favour of a C-to-C migration in the ipso product for the formation of a methoxy-substituted carbostyril derivative. One of the spiro substances is shown to participate in dienone–phenol rearrangement to provide the corresponding quinolone–phenol in high yield.

  适当的芳基取代的不对称二羧肼化合物通过氧化从双肼酰胺生成，发生分子内环化，生成各种有用的杂环化合物，如N-取代的氧杂吲哚、羧基醇、苯并氮杂哌啶、苯并氮杂呋喃、苯并咪唑酮、苯并氧杂噁唑和吡唑酮，效率各不相同。文中描述了去除杂芳香化合物中N-酰基基团的方法。在弱酸性条件下，当存在相等机会进行ipso或正常环化时，前者过程优先发生。证据支持在ipso产物中发生C到C的迁移，用于形成甲氧基取代的羧基醇衍生物。显示出某个螺旋物质参与二烯酮–酚重排，以高产率生成相应的喹啉–酚。
• Similarities and differences in the crystal packing of methoxybenzyl and methoxyphenylethyl-1,3,4-oxadiazole-2(3H)-thiones
  作者：Imtiaz Khan、Aliya Ibrar、Jim Simpson

  DOI：10.1039/c3ce42000k

  日期：——

  This work reports the crystal and molecular structures of five 1,3,4-oxadiazol-2(3H)-thiones derived from 2, 3 and 4-methoxy substituted 2-phenylacetic acid and 2- and 4-methoxy substituted 3-phenylpropanoic acid. The methoxybenzyl-1,3,4-oxadiazol-2(3H)-thiones are V-shaped while the corresponding methoxyphenylethyl-systems are close to planar, which impacts the solid state molecular packing arrangement

  这项工作报告了五种1,3,4-恶二唑-2（3 H）-硫酮的晶体和分子结构，它们分别来自2、3和4-甲氧基取代的2-苯基乙酸以及2-和4-甲氧基取代的3-苯基丙酸酸。甲氧基苄基-1,3,4-恶二唑-2（3 H）-硫酮呈V字形，而相应的甲氧基苯基乙基系统则接近平面，这会影响固态分子的排列方式。对于分子1-4，与反向相关的N–H⋯S氢键产生R 2 2（8）环占主导地位，由C–H⋯O，C–H⋯S，C–H⋯π折衷混合物支持π⋯π接触将分子堆叠到相互连接的列中。相反，在5个不对称单元中的两个独特分子中的每一个 通过一个分子的C–H⋯S接触和另一个分子的C–H⋯O接触形成的类似分子形成N–H⋯O接触，从而生成通过一系列π⋯π堆叠相互作用相互连接的平面层。
• Synthesis, crystal structure and β-glucuronidase inhibition activity of some new hydrazinecarboxamides and their 1,2,4-triazole derivatives
  作者：Muhammad Hanif、Imtiaz Khan、Nasim Hasan Rama、Shagufta Noreen、Muhammad Iqbal Choudhary、Peter G. Jones、Mazhar Iqbal

  DOI：10.1007/s00044-011-9929-1

  日期：2012.11

  compounds were screened for their β -glucuronidase inhibition activity. Compounds 5a , 5e , 5h , and 5l exhibited an excellent β -glucuronidase inhibitory activity as compared to the standard inhibitor. Graphical Abstract A new series of hydrazinecarboxamides and their 1,2,4-triazole derivatives has been reported. The synthesized compounds were evaluated for their β -glucuronidase inhibition activity

  摘要通过将相应的酰肼（ 3a - f ）与异氰酸甲氧基苯基酯（ 4a - c ）缩合，合成了 一系列带有各种甲氧基苯基和甲氧基苯乙基的肼甲酰胺 （ 5a - n ）。通过在2 N氢氧化钠水溶液中回流，将肼甲酰胺（ 5a - n ）脱氢环化， 得到相应的甲氧基苯基和甲氧基苯乙基取代的三唑（ 6a - l ）。筛选所有合成的化合物的 β -葡糖醛酸糖苷酶抑制活性。与标准抑制剂相比，化合物 5a ， 5e ， 5h 和 5l 具有出色的 β- 葡萄糖醛酸苷酶抑制活性。 图形摘要 已经报道了一系列新的肼甲酰胺及其1,2,4-三唑衍生物。评价合成的化合物的 β- 葡萄糖醛酸苷酶抑制活性。
• PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR ALPHA AGONISTS
  申请人：Cano Ivan Collado

  公开号：US20090062358A1

  公开（公告）日：2009-03-05

  The present invention is directed to compounds represented by the following structural formula, and pharmaceutically acceptable salts, solvates and hydrates thereof, R1 is a substituted or unsubstituted group selected from C 1 -C 8 alkyl, aryl-C 0-2 -alkyl, heteroaryl-C 0-2 -alkyl, C3-C6 cycloalkylaryl-C 0-2 -alkyl or phenyl. W is O or S. R2 is H or a substituted or unsubstituted group selected from C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl and heteroaryl. X is a C 2 -C 5 alkylene linker wherein one carbon atom of the linker may be replaced with O, NH or S. Y is C, O, S, NH or a single bond. Furthermore, E is (CH 2 ) n COOH, wherein n is 0, 1, 2 or 3, or C(R3)(R4)A, wherein A is an acidic functional group such as carboxyl, carboxamide substituted or unsubstituted sulfonamide, or substituted or unsubstituted tetrazole. R3 is H, saturated or unsaturated C 1 -C 5 alkyl, C 1 -C 5 alkoxy. Additionally, R4 is H, halo, a substituted or unsubstituted group selected from C 1 -C 5 alkyl, C 1 -C 5 alkoxy, C 3 -C 6 cycloalkyl, arylC 0 -C 4 alkyl and phenyl, or R3 and R4 are combined to form a C 3 -C 4 cycloalkyl.

  本发明涉及以下结构式所代表的化合物，以及其药学上可接受的盐、溶剂合物和水合物，其中，R1是C1-C8烷基、芳基-C0-2-烷基、杂芳基-C0-2-烷基、C3-C6环烷基芳基-C0-2-烷基或苯基的取代或未取代基团。W为O或S。R2为H或C1-C6烷基、C3-C6环烷基和杂芳基的取代或未取代基团。X为C2-C5烷基链，在链中的一个碳原子可以被O、NH或S取代。Y为C、O、S、NH或单键。此外，E为(CH2)nCOOH，其中n为0、1、2或3，或C(R3)(R4)A，其中A为酸性功能基团，如羧基、羧酰基取代或未取代的磺酰胺基、取代或未取代的四唑基。R3为H、饱和或不饱和的C1-C5烷基、C1-C5烷氧基。此外，R4为H、卤素、C1-C5烷基、C1-C5烷氧基、C3-C6环烷基、芳基C0-C4烷基和苯基的取代或未取代基团，或R3和R4结合形成C3-C4环烷基。
• Tandem Ring‐Opening/Double Ring‐Closing Synthesis of 1,2,4‐Triazolo[1,5‐<i>a</i>]pyridines from Chromone‐Containing Acrylonitriles
  作者：Nikita M. Chernov、Roman P. Kustin、Yulia V. Pypa、Sergej O. Anisimov、Dar'ya V. Spiridonova、Roman V. Shutov、Igor P. Yakovlev

  DOI：10.1002/adsc.202300934

  日期：2024.1.30

  We studied a reaction of chromone-containing acrylonitriles and cyanoacrylates with acid hydrazides. This reaction turned out to be a method for the synthesis of salicyloyl-substituted 1,2,4-triazolo[1,5-a]pyridines. The synthesis developed is a tandem ring-opening/double ring-closing process. This synthetic approach is characterized by low toxic solvents (ethanol, butanol) and mediator (Et3N), 37–84%

  我们研究了含色酮的丙烯腈和氰基丙烯酸酯与酰肼的反应。该反应被证明是合成水杨酰基取代的1,2,4-三唑并[1,5- a ]吡啶的方法。所开发的合成是串联开环/双闭环工艺。这种合成方法的特点是低毒溶剂（乙醇、丁醇）和介体（Et 3 N）、37-84% 的产率、产物的非色谱分离和底物耐受性（59 个例子）。