1-phenyl-2-(3,4,5-trimethoxybenzylidene)hydrazine | 63452-43-7

• 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: 1-phenyl-2-(3,4,5-trimethoxybenzylidene)hydrazine
• 英文别名: N-(3,4,5-trimethoxybenzylidene)phenylhydrazine；N-[(3,4,5-trimethoxyphenyl)methylideneamino]aniline
• CAS: 63452-43-7
• 化学式: C₁₆H₁₈N₂O₃
• mdl: MFCD00415466
• 分子量: 286.331
• InChiKey: FPYVUFDALHDCCF-UHFFFAOYSA-N

物化性质

• 沸点：
  425.4±45.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  52.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-phenyl-2-(3,4,5-trimethoxybenzylidene)hydrazine 在 copper(II) bis(trifluoromethanesulfonate) 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 29.0h， 生成 1-benzyl-2-(3,4,5-trimethoxyphenyl)-benzimidazole
  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
• 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 1-phenyl-2-(3,4,5-trimethoxybenzylidene)hydrazine
  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

• Stereospecific Copper(II)-Catalyzed Tandem Ring Opening/Oxidative Alkylation of Donor–Acceptor Cyclopropanes with Hydrazones: Synthesis of Tetrahydropyridazines
  作者：Manmath Mishra、Pinaki Bhusan De、Sourav Pradhan、Tharmalingam Punniyamurthy

  DOI：10.1021/acs.joc.9b01506

  日期：2019.9.6

  Aerobic copper(II)-catalyzed tandem ring opening and oxidative C–H alkylation of donor–acceptor cyclopropanes with bisaryl hydrazones is accomplished to produce tetrahydropyridazines, in which copper(II) plays dual role as a Lewis acid as well as redox catalyst. The reaction is stereospecific, and optically active cyclopropanes can be reacted with high optical purities (89–98% enantiomeric excess)

  好氧铜（II）催化的串联环开环和供体-受体环丙烷与双芳基的氧化CH烷基化反应可制得四氢哒嗪，其中铜（II）既起路易斯酸的作用，又起氧化还原催化剂的作用。该反应具有立体特异性，旋光性环丙烷可以高光学纯度（过量89-98％对映异构体）进行反应。底物范围，官能团耐受性，铜（II）催化剂的双重作用以及使用空气作为氧化剂是重要的实用功能。带有3-溴芳基的产物可以高产率地与硼酸进行Pd催化的Suzuki偶联。
• Ligand-free Cu(<scp>ii</scp>)-mediated aerobic oxidations of aldehyde hydrazones leading to N,N′-diacylhydrazines and 1,3,4-oxadiazoles
  作者：Lei Liu、Suliu Feng

  DOI：10.1039/c7ob00042a

  日期：——

  A Cu(II)-mediated synthesis of N,N′-diacylhydrazines and 1,3,4-oxadiazoles from aldehyde hydrazones has been developed. This is the first time that the synthesis of N,N′-diacylhydrazines and 1,3,4-oxadiazoles using N,N-dimethylamides as the acylation reagent and O2 in air as the oxidation reagent is reported. These reactions offered several advantages including simple workups, ligand-free inexpensive

  已开发了一种由Cu（II）介导的从醛中合成N，N'-二酰基肼和1,3,4-恶二唑的方法。这是第一次发现的合成Ñ，Ñ使用'-diacylhydrazines和1,3,4-恶二唑Ñ，Ñ -dimethylamides，作为酰化试剂和O 2在空气作为氧化试剂的报道。这些反应提供了几个优点，包括简单的后处理，无配体的廉价金属盐作为介体，高收率和广泛的底物范围。
• Hydrazone Phosphaketene as a Synthetic Platform To Obtain Three Classes of 1,2,4-Diazaphosphol Derivatives by Switchable Chemoselectivity Strategies
  作者：Xin Wang、Dong-Ping Chen、Wen-Peng Wang、Chun-Hong Yang、Ming Li、Wen-Bo Xu、Xi-Cun Wang、Zheng-Jun Quan

  DOI：10.1021/acs.orglett.4c00993

  日期：2024.5.3

  classes of 1,2,4-diazaphosphol derivatives. First, the five-membered heterocyclic P and O anion intermediates acted as nucleophilic agents in the selective construction of C–P and C–O bonds. Second, the phosphinidene served as a phosphorus synthon, allowing for the formation of C–P and C–N bonds. Finally, a stepwise mechanism, supported by DFT calculations, was invoked to explain the reaction selectivity

  我们引入基于腙磷烯中间体的可切换化学选择性策略来合成三类 1,2,4-二氮杂磷衍生物。首先，五元杂环P和O阴离子中间体在C-P和C-O键的选择性构建中充当亲核试剂。其次，膦亚基充当磷合成子，允许形成 C-P 和 C-N 键。最后，利用 DFT 计算支持的逐步机制来解释反应选择性。
• Copper-catalyzed aerobic annulation of hydrazones with dienones: an efficient route to pyrazole-linked hybrid molecules
  作者：Kalinga H. Nayak、Robert K. Jijin、Mariswamy K. Sreelekha、Beneesh P. Babu

  DOI：10.1039/d4ob00825a

  日期：——

  A copper-catalyzed aerobic [3 + 2] annulation reaction to access various pyrazole-bound chalcones starting from readily available and cost-effective hydrazones and dienones is reported. These pyrazole-bound chalcones were further utilized effectively to prepare a series of pyrazole-linked hybrid molecules, such as pyrazole–pyrazoline, pyrazole–aziridine, and pyrazole–pyridine hybrids by efficient simple

  报道了一种铜催化的有氧 [3 + 2] 成环反应，从容易获得且具有成本效益的腙和二烯酮开始获得各种吡唑结合的查耳酮。这些吡唑结合的查耳酮被进一步有效地利用，通过有效的简单转化制备了一系列吡唑连接的杂化分子，例如吡唑-吡唑啉、吡唑-氮丙啶和吡唑-吡啶杂化物。在有氧铜催化下，通过简单的两步过程获得了具有高原子经济性的具有合成挑战性的杂化分子。
• A Convenient One-Pot Conversion of Arene- and Heteroarenecarboxaldehyde Phenylhydrazones into Nitriles via Reaction with<i>N,N</i>-Dimethyldichloromethaniminium Chloride
  作者：Bruno Kokel、Gabriel Menichi、Michel Hubert-Habart

  DOI：10.1055/s-1985-31154

  日期：——