(4-chlorophenyl)(pyrimidin-2-yl)methanone | 64385-81-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-chlorophenyl)(pyrimidin-2-yl)methanone
• 英文别名: (4-chloro-phenyl)-pyrimidin-2-yl-methanone；2-(4-Chlorobenzoyl)pyrimidine；(4-chlorophenyl)-pyrimidin-2-ylmethanone
• CAS: 64385-81-5
• 化学式: C₁₁H₇ClN₂O
• mdl: MFCD00160472
• 分子量: 218.642
• InChiKey: CQXSPCXVLBTZST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-溴氯苯 、 (4-chlorophenyl)(pyrimidin-2-yl)methanone 在 叔丁基锂 作用下， 以 四氢呋喃 、 正庚烷 为溶剂， 反应 1.5h， 以16%的产率得到(2-chlorophenyl)(4-chlorophenyl)pyrimidin-2-yl methanol
  参考文献：
  名称：

  Analogues of Fenarimol Are Potent Inhibitors of Trypanosoma cruzi and Are Efficacious in a Murine Model of Chagas Disease

  摘要：

  We report the discovery of nontoxic fungicide fenarimol (1) as an inhibitor of Trypanosoma cruzi (T. cruzi), the causative agent of Chagas disease, and the results of structure-activity investigations leading to potent analogues with low nM IC(50)s in a T. cruzi whole cell in vitro assay. Lead compounds suppressed blood parasitemia to virtually undetectable levels after once daily oral dosing in mouse models of T. cruzi infection. Compounds are chemically tractable, allowing rapid optimization of target biological activity and drug characteristics. Chemical and biological studies undertaken in the development of the fenarimol series toward the goal of delivering a new drug candidate for Chagas disease are reported.

  DOI：

  10.1021/jm2015809
• 作为产物：
  描述：

  2-甲基嘧啶 在 copper(l) iodide 、 palladium(II) trifluoroacetate 、 氧气 、 caesium carbonate 、 溶剂黄146 、 lithium hexamethyldisilazane 、 三环己基膦 作用下， 以 四氢呋喃 、 乙基苯 、 二甲基亚砜 、 甲苯 为溶剂， 反应 30.0h， 生成 (4-chlorophenyl)(pyrimidin-2-yl)methanone
  参考文献：
  名称：

  通过铜和铁催化氧化芳基（二）az嗪基甲烷的亚甲基合成芳基（二）az嗪基酮

  摘要：

  可持续的氧化：描述了一种将芳基（二）叠氮基甲烷转化为芳基（二）叠氮基酮的氧化方法。使用贱金属（铜和铁）作为催化剂，并结合使用O 2作为氧化剂，这使该方法具有可持续性。该方法的实用性通过6-（4-甲基苯甲酰基）吡啶-2-甲醛的合成来说明，该中间体是制备药物卡维他汀的中间体。

  DOI：

  10.1002/anie.201108540

文献信息

• Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen
  作者：Hans Sterckx、Johan De Houwer、Carl Mensch、Wouter Herrebout、Kourosch Abbaspour Tehrani、Bert U W Maes

  DOI：10.3762/bjoc.12.16

  日期：——

  The methylene group of various substituted 2- and 4-benzylpyridines, benzyldiazines and benzyl(iso)quinolines was successfully oxidized to the corresponding benzylic ketones using a copper or iron catalyst and molecular oxygen as the stoichiometric oxidant. Application of the protocol in API synthesis is exemplified by the alternative synthesis of a precursor to the antimalarial drug Mefloquine. The oxidation method can also be used to prepare metabolites of APIs which is illustrated for the natural product papaverine. ICP–MS analysis of the purified reaction products revealed that the base metal impurity was well below the regulatory limit.

  各种取代的2-和4-苄基吡啶、苄基二嗪和苄基(异)喹啉的亚甲基基团成功地被氧化为相应的苄基酮，使用铜或铁催化剂和分子氧作为化学计量氧化剂。该方案在API合成中的应用以替代合成抗疟药物美氟喹的前体为例。这种氧化方法还可用于制备API的代谢产物，以天然产物樟碱为例进行说明。对纯化的反应产物进行ICP-MS分析显示，基础金属杂质远低于监管限值。
• Overcoming Electron-Withdrawing and Product-Inhibition Effects by Organocatalytic Aerobic Oxidation of Alkylpyridines and Related Alkylheteroarenes to Ketones
  作者：Hua Wang、Jie Liu、Jian-Ping Qu、Yan-Biao Kang

  DOI：10.1021/acs.joc.9b03205

  日期：2020.3.6

  An organocatalyzed aerobic benzylic C-H oxidation of alkyl and aryl heterocycles has been developed. This transition metal-free method is able to overcome the electron-withdrawing effect as well as product-inhibition effects in heterobenzylic radical oxidation. A variety of ketones bearing N-heterocyclic groups could be prepared under relatively mild conditions with moderate to high yields.

  已经开发了烷基和芳基杂环的有机催化的需氧苄基CH氧化。这种无过渡金属的方法能够克服杂苄基自由基氧化中的吸电子作用以及产物抑制作用。可以在相对温和的条件下以中等至高产率制备各种带有N-杂环基的酮。
• Batori, S.; Messmer, A., Journal of Heterocyclic Chemistry, 1994, vol. 31, # 4, p. 1041 - 1046
  作者：Batori, S.、Messmer, A.

  DOI：——

  日期：——
• SAUTER F.; STANETTY P.; MESBAH A., J. CHEM. RES. SYNOP., 1977, NO 7, 186
  作者：SAUTER F.、 STANETTY P.、 MESBAH A.

  DOI：——

  日期：——
• [EN] ORGANIC COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING SAME<br/>[FR] COMPOSÉ ORGANIQUE ET DISPOSITIF ÉLECTROLUMINESCENT ORGANIQUE LE COMPRENANT<br/>[KO] 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
  申请人：DOOSAN CORP

  公开号：WO2018080065A1

  公开（公告）日：2018-05-03

  본 발명은 신규 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것으로서, 본 발명에 따른 화합물은 유기 전계 발광 소자의 유기물층, 바람직하게는 발광층에 사용됨에 따라 유기 전계 발광 소자의 발광 효율, 구동 전압, 수명 등을 향상시킬 수 있다.