N-(3,4-dimethoxybenzylidene)phenylhydrazine | 55754-32-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3,4-dimethoxybenzylidene)phenylhydrazine
• 英文别名: 3,4-dimethoxybenzaldehyde phenylhydrazone；1-[(3,4-Dimethoxyphenyl)methylidene]-2-phenylhydrazine；N-[(3,4-dimethoxyphenyl)methylideneamino]aniline
• CAS: 55754-32-0
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: YQNSBWJQNNQCMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  42.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  N-(3,4-dimethoxybenzylidene)phenylhydrazine 在 bismuth(III) chloride 、 benzyltriphenylphosphonium peroxymonosulfate 作用下， 以 乙腈 为溶剂， 反应 3.5h， 以30%的产率得到3,4-二甲氧基苯甲醛
  参考文献：
  名称：

  肟、苯腙、2,4-二硝基苯腙和亚氨基脲与苄基三苯基膦过氧单硫酸盐（BnPh3P+双锍-四氢呋喃）的相应羰基化合物的转化

  摘要：

  已发现苄基三苯基鏻过氧单硫酸盐 (BTPPMS) (1) 是一种有效的新型试剂，可用于将肟、苯腙、2,4-二硝基苯腙和缩氨基脲转化为相应的羰基化合物。该反应在乙腈中在回流条件下在催化量的氯化铋存在下进行。

  DOI：

  10.1081/scc-100106197
• 作为产物：
  描述：

  苯胺 在 盐酸 、 sodium acetate 、 sodium nitrite 作用下， 以 乙醇 、 水 为溶剂， 反应 0.75h， 生成 N-(3,4-dimethoxybenzylidene)phenylhydrazine
  参考文献：
  名称：

  Copper-Mediated Synthesis of Substituted 2-Aryl-N-benzylbenzimidazoles and 2-Arylbenzoxazoles via C–H Functionalization/C–N/C–O Bond Formation

  摘要：

  An efficient method for the transformation of N-benzyl bisarylhydrazones and bisaryloxime ethers to functionalized 2-aryl-N-benzylbenzimidazoles and 2-arylbenzoxazoles is described. The protocol involves a copper(II)-mediated cascade C-H functionalization/C-N/C-O bond formation under neutral conditions. Substrates having either electron-donating or -withdrawing substituents undergo the cyclization to afford the target heterocycles at moderate temperature.

  DOI：

  10.1021/jo2005632

文献信息

• Synthesis of 3,4-diaryl-1-phenyl-4,5-dihydro-1$H$-pyrazole-5-carbonitriles via 1,3-dipolar cycloaddition reactions
  作者：Jayaroopa PRABHASHANKAR、Vasanth Kumar GOVINDAPPA、Ajay Kumar KARIYAPPA

  DOI：10.3906/kim-1209-52

  日期：——

  Nitrile imines generated by the oxidative dehydrogenation of aromatic aldehyde phenylhydrazones with chloramine-T as a catalytic dehydrogenating agent were trapped in situ by 4-methoxy cinnamonitrile to afford 3,4-diaryl-1-phenyl-4,5-dihydro-1H-pyrazole-5-carbonitrile in moderate to good yields. The structures of the cycloadducts were confirmed by spectral studies and elemental analysis.

  通过使用氯胺-T作为催化脱氢剂，对芳香醛苯肼酮进行氧化脱氢反应生成的腈亚胺，立即与4-甲氧基肉桂腈捕获，从而在中等至良好的产率下得到3,4-二芳基-1-苯基-4,5-二氢-1H-吡唑-5-腈。通过光谱研究和元素分析确认了环加成产物的结构。
• From Phenylhydrazone to 1 <i>H</i> ‐1,2,4‐Triazoles via Nitrification, Reduction and Cyclization
  作者：Liqiang Hao、Guodong Wang、Jian Sun、Jun Xu、Hongshuang Li、Guiyun Duan、Chengcai Xia、Pengfei Zhang

  DOI：10.1002/adsc.201901563

  日期：2020.4.17

  cyclization protocol employing cobalt nitrate and 1,2‐dichloroethane to produce substituted 1H‐1,2,4‐triazoles. Notably, 1,2‐dichloroethane serves both the solvent and a hydrogen source for transfer hydrogenation. This methodology works under mild conditions, providing a direct approach for the synthesis of 1H‐1,2,4‐triazoles.

  在本文中，我们报告了通过硝化，还原，环化方案，采用硝酸钴和1,2-二氯乙烷进行串联硝化，生成取代的1 H -1,2,4-三唑。值得注意的是，1,2-二氯乙烷既是溶剂又是转移氢化的氢源。这种方法在温和的条件下有效，为合成1 H -1,2,4-三唑提供了直接的方法。
• Ce-catalyzed regioselective synthesis of pyrazoles from 1,2-diols <i>via</i> tandem oxidation and C–C/C–N bond formation
  作者：Chandan Kumar Pal、Ashis Kumar Jena

  DOI：10.1039/d2ob01996e

  日期：——

  novel and efficient cerium-catalyzed tandem oxidation and intermolecular ring cyclization of vicinal diols with hydrazones has been achieved for the regioselective synthesis of pyrazole derivatives. The corresponding 1,3-di- and 1,3,5-trisubstituted pyrazoles were obtained in moderate to excellent yields. The reaction has the advantages of mild conditions, easily available starting materials, broad substrate

  已经实现了一种新型高效的铈催化串联氧化和邻位二醇与腙的分子间环化，用于吡唑衍生物的区域选择性合成。相应的 1,3-二和 1,3,5-三取代吡唑以中等到极好的产率获得。该反应条件温和、起始原料易得、底物适用范围广、官能团耐受性好。
• Visible-light-absorbing C–N cross-coupling for the synthesis of hydrazones involving C(sp²)–H/C(sp³)–H functionalization
  作者：Ambuj Kumar Kushwaha、Suresh Kumar Maury、Arsala Kamal、Himanshu Kumar Singh、Shikha Pandey、Sundaram Singh

  DOI：10.1039/d2cc07001d

  日期：——

  An efficient C–N cross-coupling approach for the synthesis of hydrazones was developed through C(sp2)–H and C(sp3)–H functionalization of indole and methylarene under visible light irradiation using photocatalyst eosin Y, ethanol:water as a green solvent and atmospheric air as an oxidant. With the aid of eosin Y, the C–H bonds of indole and methylarenes were activated followed by coupling with arylhydrazines

  通过 C(sp 2 )–H 和 C(sp 3)–H 功能化吲哚和甲基芳烃在可见光照射下使用光催化剂曙红 Y，乙醇：水作为绿色溶剂和大气空气作为氧化剂。在曙红 Y 的帮助下，吲哚和甲基芳烃的 C-H 键被激活，然后与芳基肼偶联。该程序适用于具有良好官能团相容性的各种底物，提供了一种创造性的方法，可以用廉价且易于获得的原材料制造腙。没有金属、低成本、环境友好、绿色溶剂、无毒、易于处理以及利用可见光等可再生能源是该方法的一些主要优势。
• Diaryl Hydrazones as Multifunctional Inhibitors of Amyloid Self-Assembly
  作者：Béla Török、Abha Sood、Seema Bag、Rekha Tulsan、Sanjukta Ghosh、Dmitry Borkin、Arleen R. Kennedy、Michelle Melanson、Richard Madden、Weihong Zhou、Harry LeVine、Marianna Török

  DOI：10.1021/bi3012059

  日期：2013.2.19

  The design and application of an effective, new class of multifunctional small molecule inhibitors of amyloid self-assembly are described. Several compounds based on the diaryl hydrazone scaffold were designed. Forty-four substituted derivatives of this core structure were synthesized using a variety of benzaldehydes and phenylhydrazines and characterized. The inhibitor candidates were evaluated in multiple assays, including the inhibition of amyloid beta (A beta) fibrillogenesis and oligomer formation and the reverse processes, the disassembly of preformed fibrils and oligomers. Because the structure of the hydrazone-based inhibitors mimics the redox features of the antioxidant resveratrol, the radical scavenging effect of the compounds was evaluated by colorimetric assays against 2,2-diphenyl-1-picrylhydrazyl and superoxide radicals. The hydrazone scaffold was active in all of the different assays. The structure-activity relationship revealed that the substituents on the aromatic rings had a considerable effect on the overall activity of the compounds. The inhibitors showed strong activity in fibrillogenesis inhibition and disassembly, and even greater potency in the inhibition of oligomer formation and oligomer disassembly. Supporting the quantitative fluorometric and colorimetric assays, size exclusion chromatographic studies indicated that the best compounds practically eliminated or substantially inhibited the formation of soluble, aggregated A beta species, as well. Atomic force microscopy was also applied to monitor the morphology of A beta deposits. The compounds also possessed the predicted antioxidant properties; approximately 30% of the synthesized compounds showed a radical scavenging effect equal to or better than that of resveratrol or ascorbic acid.