3',5'-dimethyl-4-cyano-diphenyl ether | 24789-53-5

• 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: 3',5'-dimethyl-4-cyano-diphenyl ether
• 英文别名: 3',5'-dimethyl-4-cyanodiphenyl ether；4-(3,5-dimethylphenoxy)benzonitrile；3,5-dimethylphenyl 4-cyanophenyl ether；4-(3,5-dimetylphenoxy)-benzonitrile；4-(3,5-Xylylphenoxy)-benzonitril
• CAS: 24789-53-5
• 化学式: C₁₅H₁₃NO
• mdl: MFCD08446950
• 分子量: 223.274
• InChiKey: YWJWHNIUCSBDOX-UHFFFAOYSA-N

物化性质

• 熔点：
  58 °C
• 沸点：
  352.1±30.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3',5'-dimethyl-4-cyano-diphenyl ether 在 盐酸 、 硫酸 、 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 4-(3,5-dimethylphenoxy)-N-[(1S)-1-{[(3S)-4-(3-hydroxyphenyl)-3-methylpiperazin-1-yl]methyl}-2-methylpropyl]benzamide dihydrochloride
  参考文献：
  名称：

  Discovery of N-{4-[(3-Hydroxyphenyl)-3-methylpiperazin-1-yl]methyl-2-methylpropyl}-4-phenoxybenzamide Analogues as Selective Kappa Opioid Receptor Antagonists

  摘要：

  There is continuing interest in the discovery and development of new kappa opioid receptor antagonists. We recently reported that N-substituted 3-methyl-4-(3-hydroxyphenyl)piperazines were a new class of opioid receptor antagonists. In this study, we report the syntheses of two piperazine JDTic-like analogues. Evaluation of the two compounds in an in vitro [S-35]GTP gamma S binding assay showed that neither compound showed the high potency and kappa opioid receptor selectivity of JDTic. A library of compounds using the core scaffold 21 was synthesized and tested for their ability to inhibit [S-35]GTP gamma S binding stimulated by the selective kappa opioid agonist U69,593. These studies led to N-[(1S)-1-{[(3S)-4-(3-hydroxyphenyl)-3-methylpiperazin-1-yl]methyll-2-methylpropyl]-4-phenoxybenzamide (11a), a compound that showed good kappa opioid receptor antagonist properties. An SAR study based on 11a provided 28 novel analogues. Evaluation of these 28 compounds in the [S-35]GTP gamma S binding assay showed that several of the analogues were potent and selective kappa opioid receptor antagonists.

  DOI：

  10.1021/jm400275h
• 作为产物：
  描述：

  对氯苯甲腈 、 3,5-二甲基苯酚 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以98%的产率得到3',5'-dimethyl-4-cyano-diphenyl ether
  参考文献：
  名称：

  亲核芳香取代与催化之间的前沿

  摘要：

  报道了使用有或没有金属催化剂的活化卤代芳烃对杂原子亲核试剂进行芳基化的研究。提出了有关微量金属参与的讨论，并在没有添加金属催化剂的情况下受到意想不到的“配体”效应的支持。我们认为，亲核芳香族取代和催化之间的边界可能比通常认为的更加难以界定。

  DOI：

  10.1002/chem.201304164

文献信息

• Selective One‐Pot Access to Symmetrical or Unsymmetrical Diaryl Ethers by Copper‐Catalyzed Double Arylation of a Simple Oxygen Source
  作者：Anis Tlili、Florian Monnier、Marc Taillefer

  DOI：10.1002/chem.201001373

  日期：2010.11.2

  Great CO‐mbination: A novel method is reported for the controlled one‐pot synthesis of various symmetrical or unsymmetrical diaryl ethers by double arylation of a simple inorganic oxygen source (see scheme). This versatile and highly selective process is based on the use of a cheap and low toxicity copper catalytic system.

  出色的结合：据报道，通过简单的无机氧源的双芳基化，可控制的一锅合成各种对称或不对称的二芳基醚的新方法。这种通用且高度选择性的过程基于使用廉价且低毒性的铜催化系统。
• Method of forming a carbon-carbon or carbon-heteroatom linkage
  申请人：Taillefer Marc

  公开号：US20050234239A1

  公开（公告）日：2005-10-20

  The invention relates to a method of creating a carbon-carbon or carbon-heteroatom linkage by reacting an unsaturated compound bearing a leaving group and a nucleophilic compound. More specifically, the invention relates to the creation of a carbon-nitrogen linkage involving the arylation of nitrogenous organic derivatives. The inventive method consists in creating a carbon-carbon or carbon-heteroatom linkage by reacting an unsaturated compound bearing a leaving group and a nucleophilic compound providing a carbon atom or a heteroatom (HE) capable of being substituted for the leaving group, thereby creating a C—C or C-HE linkage. The invention is characterised in that the reaction is carried out in the presence of an effective quantity of a catalyst based on copper and at least one ligand comprising at least one imine function and at least one additional nitrogen atom as chelating atoms

  该发明涉及一种通过使带有离去基团和亲核化合物的不饱和化合物发生反应来创建碳-碳或碳-杂原子键的方法。更具体地，该发明涉及涉及通过芳基化氮有机衍生物来创建碳-氮键。该创新方法包括通过使带有离去基团和提供能够替代离去基团的碳原子或杂原子（HE）的亲核化合物发生反应来创建碳-碳或碳-杂原子键。该发明的特点在于，在铜基催化剂和至少包含至少一个亚胺功能和至少一个额外氮原子作为螯合原子的配体的有效量存在下进行反应。
• New Catalytic System for Cross-Coupling Reactions
  申请人：Taillefer Marc

  公开号：US20110306782A1

  公开（公告）日：2011-12-15

  The present invention concerns a process for creating a Carbon-Carbon bond (C—C) or a Carbon-Heteroatom bond (C-HE) by reacting a compound carrying a leaving group with a nucleophilic compound carrying a carbon atom or a heteroatom (HE) that can substitute for the leaving group, creating a C—C or C-HE bond, wherein the reaction takes place in the presence of an effective quantity of a. a catalytic system comprising a ligand and at least a metal-based catalyst, such a metal catalyst being chosen among iron or copper compounds proviso that only a single metal is present.

  本发明涉及一种通过使带有离去基团的化合物与带有可以替代离去基团的碳原子或杂原子（HE）的亲核化合物反应，从而形成碳-碳键（C—C）或碳-杂原子键（C-HE）的过程，其中反应在存在有效量的a.由配体和至少一种基于金属的催化剂组成的催化系统的条件下进行，所述金属催化剂选自铁或铜化合物，但需注意只存在单一金属。
• Copper(I)–USY as a Ligand-Free and Recyclable Catalyst for Ullmann-Type <i>O</i>-, <i>N</i>-, <i>S</i>-, and <i>C</i>-Arylation Reactions: Scope and Application to Total Synthesis
  作者：Tony Garnier、Mathieu Danel、Valentin Magné、Anthony Pujol、Valérie Bénéteau、Patrick Pale、Stefan Chassaing

  DOI：10.1021/acs.joc.8b00620

  日期：2018.6.15

  copper(I)-doped zeolite CuI–USY proved to be a versatile, efficient, and recyclable catalyst for various Ullmann-type coupling reactions. Easy to prepare and cheap, this catalytic material enables the arylation and heteroarylation of diverse O-, N-, S-, and C-nucleophiles under ligand-free conditions while exhibiting large functional group compatibility. The facility of this catalyst to promote C–O bond

  掺杂铜（I）的沸石Cu I- USY被证明是用于各种Ullmann型偶联反应的通用，高效且可回收的催化剂。这种催化材料易于制备且价格便宜，可在无配体的条件下实现多种O-，N-，S-和C-亲核试剂的芳基化和杂芳基化，同时具有大的官能团相容性。这种催化剂促进C-O键形成的功能在3-甲基obovatol（一种具有生物学相关性的天然存在的二芳基醚）的全合成中得到了进一步证明。从机理的角度出发，已经提出了两种竞争途径，这取决于亲核试剂的性质并与所获得的结果一致。
• 一种水解二芳醚化合物生成芳基酚类化合物的方法
  申请人：华东师范大学

  公开号：CN113443965B

  公开（公告）日：2022-09-20

  本发明公开了一种水解二芳醚化合物生成芳基酚类化合物的方法，所述方法利用可见光激发光敏剂催化。在反应溶剂中，式(1)原料在酸的辅助作用下，断裂C(sp2)‑O键，水解获得式(3)和式(4)两分子芳基酚类化合物。本发明能在在室温下催化反应，绿色环保，操作简单；普适性广、反应收率较高、官能团耐受性强；合成方法不仅可以实现小规模各种二芳醚化合物的水解转化，还可以实现除草醚、三氯生和木质素模板底物的水解，甚至可以大规模水解三氯生和木质素模板底物，实现克级降解，为木质素水解回收苯酚衍生物、降解农药、含除菌剂或除草剂的废水净化提供了新的策略。本发明具有广泛的应用前景和使用价值。

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