(4-氯苯基)-萘-2-基甲酮 | 7495-98-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (4-氯苯基)-萘-2-基甲酮
• 英文名称: (4-chlorophenyl)(naphthalen-2-yl)methanone
• 英文别名: β-naphthyl-4-chlorophenyl-ketone；(4-chlorophenyl)(2-naphthyl)methanone；2-naphthyl 4-chlorophenyl ketone；4-chlorophenyl 2-naphthyl ketone；(4-chloro-phenyl)-[2]naphthyl ketone；(4-Chlor-phenyl)-[2]naphthyl-keton；(4-Chlorophenyl)-naphthalen-2-ylmethanone
• CAS: 7495-98-9
• 化学式: C₁₇H₁₁ClO
• mdl: MFCD12541689
• 分子量: 266.727
• InChiKey: CTHWFRNTSNRVTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4-氯苯基)-萘-2-基甲酮 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以97%的产率得到(4-chlorophenyl)(naphthalene-2-yl)methanol
  参考文献：
  名称：

  Research on antibacterial and antifungal agents. 16. Synthesis and antifungal activities of 1-[α-(1-naphthyl)benzyl]imidazole derivatives and related 2-naphthyl isomers

  摘要：

  Some 1-arylmethylimidazoles bearing a naphthyl group at the a position of benzyl moiety have been synthesized and tested as antifungal agents against Candida albicans and Candida spp. Such derivatives resemble bifonazole and naftifine, two important antimycotic agents of clinical use. Various compounds were found highly active when tested against Candida strains in comparison with bifonazole, miconazole, clotrimazole and ketoconazole.

  DOI：

  10.1016/0223-5234(92)90089-j
• 作为产物：
  描述：

  4-氯苯基溴化镁 在 乙醚 、 苯 作用下， 生成 (4-氯苯基)-萘-2-基甲酮
  参考文献：
  名称：

  The Synthesis of 7-Chloro-10-methyl-1,2-benzanthracene and Related Compounds¹

  摘要：

  DOI：

  10.1021/ja01270a025

文献信息

• Palladium-Catalyzed Denitrogenative Synthesis of Aryl Ketones from Arylhydrazines and Nitriles Using O₂ as Sole Oxidant
  作者：Xu Wang、Yubing Huang、Yanli Xu、Xiaodong Tang、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/acs.joc.6b02697

  日期：2017.2.17

  An efficient and simple palladium-catalyzed approach for the synthesis of aryl ketones from low-cost nitriles and arylhydrazines using molecular oxygen (O2) as sole oxidant via C–N bond cleavage is reported. Various aryl ketones were synthesized in moderate to good yields under mild conditions. A possible mechanism involving the PdII/Pd0 catalytic cycle process is depicted, and a cationic palladium

  据报道，一种有效且简单的钯催化方法可通过低成本的腈和芳肼，使用分子氧（O 2）作为唯一氧化剂通过C–N键断裂来合成芳基酮。在温和的条件下以中等至良好的产率合成了各种芳基酮。描述了涉及Pd II / Pd 0催化循环过程的可能机理，并通过ESI-MS检测了阳离子钯中间体。
• Electroorganic reactions. Part 56: Anodic oxidation of 2-methyl- and 2-benzylnaphthalenes: factors influencing competing pathways
  作者：James H.P Utley、Gregor G Rozenberg

  DOI：10.1016/s0040-4020(02)00495-7

  日期：2002.6

  carbon. However, little side-chain anodic oxidation is observed under any conditions tried; the radical–cations of electron-rich substrates preferentially dimerise and a strongly electron-withdrawing substituent at the 6-position (EtOSO2) promotes nuclear substitution. In contrast, oxidation with DDQ in aqueous acetic acid gives efficient side-chain oxidation for electron rich substrates, consistent

  系统地研究了在萘核的6位和苄基侧链的4-苯基位取代的2-甲基和2-苄基萘在亲核介质中的阳极氧化作用，以确定有利于环境的因素侧链取代。循环伏安法证实6-取代对萘核的氧化电位有深远的影响，13 C化学位移表明在苄基碳上有极性作用。然而，在任何尝试的条件下，几乎都没有观察到侧链阳极氧化。富电子底物的自由基阳离子优先二聚，并且在6位上具有强吸电子取代基（EtOSO 2）促进核替代。相反，在含水乙酸中用DDQ氧化可对富含电子的底物进行有效的侧链氧化，这与氢化物转移（可能在分子内通过电荷转移络合物）转移一致。
• Iron-catalyzed carbonylation of aryl halides with arylborons using stoichiometric chloroform as the carbon monoxide source
  作者：Hongyuan Zhao、Hongyan Du、Xiaorong Yuan、Tianjiao Wang、Wei Han

  DOI：10.1039/c6gc02158a

  日期：——

  A general iron-catalyzed carbonylative Suzuki-Miyaura coupling of aryl halides with arylborons is reported, using stoichiometric CHCl3 as the CO source. The high efficiency, economy, selectivity, and operational simplicity of this...

  据报道，使用化学计量的CHCl3作为一氧化碳源，一般的铁催化的芳基卤化物与芳基硼的羰基化Suzuki-Miyaura偶联反应。该解决方案的高效，经济，选择性和操作简便性...
• Transition-metal-free, ambient-pressure carbonylative cross-coupling reactions of aryl halides with potassium aryltrifluoroborates
  作者：Fengli Jin、Wei Han

  DOI：10.1039/c5cc01968k

  日期：——

  We disclose an unprecedented transition-metal-free carbonylative cross coupling of aryl halides with potassium aryl trifluoroborates even at atmospheric pressure of carbon monoxide. This protocol is efficient, operationally simple, and shows...

  我们公开了空前的无过渡金属的芳基卤化物与芳基三氟硼酸钾的无过渡金属羰基交叉偶合，即使在一氧化碳的大气压下也是如此。该协议高效，操作简单，并显示...
• Pd-Catalyzed Suzuki-Miyaura Cross-Coupling of Arylboronic Acids and α-Iminonitriles through C-CN Bond Activation
  作者：Kui Liu、Shou-Wei Tao、Chun Qian、Yong-Ming Zhu

  DOI：10.1002/ejoc.201800857

  日期：2018.9.16

  A valuable method for the Pd‐catalyzed Suzuki–Miyaura cross‐coupling of arylboronic acids has been developed, using α‐iminonitriles to replace acylnitriles. The reaction proceeds through selective activation of the C–CN bond, and avoids the “decarbonylation” side reaction of acylnitriles after activation.

  已经开发出一种有价值的方法，可使用α-亚氨基腈代替乙腈，对Pd催化的Suzuki-Miyaura芳基硼酸进行交叉偶联。该反应通过选择性激活C-CN键进行，避免了活化后腈的“脱羰”副反应。