N-cyclohexyl-3-(trifluoromethyl)benzamide | 418795-69-4

• 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-cyclohexyl-3-(trifluoromethyl)benzamide
• CAS: 418795-69-4
• 化学式: C₁₄H₁₆F₃NO
• 分子量: 271.282
• InChiKey: VEJZPCMVCZDUIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  西那卡塞杂质108 、 环己基异氰酸酯 在 1,1'-双(二苯基膦)二茂铁 、 锰 、 氯化镍二甲氧基乙烷 、 sodium iodide 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 24.0h， 以82%的产率得到N-cyclohexyl-3-(trifluoromethyl)benzamide
  参考文献：
  名称：

  Ni-Catalyzed Direct Reductive Amidation via C–O Bond Cleavage

  摘要：

  A novel Ni-catalyzed reductive amidation of C(sp(2))-O and C(sp(3))-O electrophiles with isocyanates is described. This umpolung reaction allows for an unconventional preparation of benzamides using simple starting materials and easy-to-handle Ni catalysts.

  DOI：

  10.1021/ja5029793

文献信息

• Decarboxylative sp3 C–N coupling via dual copper and photoredox catalysis
  作者：Yufan Liang、Xiaheng Zhang、David W. C. MacMillan

  DOI：10.1038/s41586-018-0234-8

  日期：2018.7

  to construct sp2 carbon–nitrogen (C–N) bonds using palladium, copper or nickel catalysis1,2. However, the incorporation of alkyl substrates to form sp3 C–N bonds remains one of the major challenges in the field of cross-coupling chemistry. Here we demonstrate that the synergistic combination of copper catalysis and photoredox catalysis can provide a general platform from which to address this challenge

  在过去的三十年中，利用钯、铜或镍催化构建 sp2 碳氮 (C-N) 键的方法的开发取得了相当大的进展1,2。然而，结合烷基底物形成sp3 C-N键仍然是交叉偶联化学领域的主要挑战之一。在这里，我们证明铜催化和光氧化还原催化的协同组合可以提供一个通用平台来应对这一挑战。该交叉偶联系统使用天然丰富的烷基羧酸和市售的氮亲核试剂作为偶联伙伴。它适用于各种伯、仲和叔烷基羧酸（通过碘鎓活化），以及大量氮亲核试剂：氮杂环、酰胺、磺酰胺和苯胺可以进行 C-N 偶联，提供 N-在室温下和短时间内（五分钟到一小时），烷基产品的效率从良好到优异。我们证明，这种 C-N 偶联方案使用含有多个胺基的底物进行高区域选择性，并且还可以应用于复杂的药物分子，从而能够快速构建分子复杂性和生物活性药物的后期功能化。铜催化和光氧化还原催化的结合在快速、室温偶联方案中形成 sp3 C-N 键，具有高效率和区域选择性以及广泛的底物范围。
• Pd(ii)-catalyzed decarboxylative cross-coupling of oxamic acids with potassium phenyltrifluoroborates under mild conditions
  作者：Mingzong Li、Cong Wang、Ping Fang、Haibo Ge

  DOI：10.1039/c1cc11635e

  日期：——

  A novel Pd-catalyzed decarboxylative cross-coupling of oxamic acids with potassium phenyltrifluoroborates has been realized under mild reaction conditions. This method provides an efficient access to N-mono- or N,N-disubstituted benzamides and benzoates.

  在温和反应条件下，实现了钯催化下的草氨酸与苯基三氟硼酸钾的去羧偶联反应。该方法为制备N-单取代或N,N-双取代苯甲酰胺和苯甲酸酯提供了高效的途径。
• Ruthenium-catalyzed oxidative decyanative cross-coupling of acetonitriles with amines in air: a general access to primary to tertiary amides under mild conditions
  作者：Yuguang Wang、Zhongli Wu、Qin Li、Bingchun Zhu、Lei Yu

  DOI：10.1039/c7cy00761b

  日期：——

  Catalyzed by Ru and in the presence of air and nucleophiles such as amines or ammonia, activation of the C–CN bond could be easily achieved under mild conditions to produce primary to tertiary amides in good to excellent yields. The use of accessible and functional-group-tolerant starting materials, a cheap, low-loading and recyclable catalyst, ligand-free conditions and excellent product yields are

  在钌的催化下，在空气和亲核试剂（例如胺或氨）的存在下，在温和条件下可以很容易地实现C-CN键的活化，从而以良好或优异的产率生产伯酰胺至叔酰胺。该方法的优点是使用易接近且具有功能基团耐受性的起始原料，廉价，低载和可循环使用的催化剂，无配体的条件以及优异的产物收率。而且，与Ritter反应和水合方法相比，该新颖反应具有更广泛的应用范围。
• Design, synthesis and structure–activity relationship of novel inhibitors against H5N1 hemagglutinin-mediated membrane fusion
  作者：Zhibo Zhu、Runming Li、Gaokeng Xiao、Zhipeng Chen、Jie Yang、Qiuhua Zhu、Shuwen Liu

  DOI：10.1016/j.ejmech.2012.08.041

  日期：2012.11

  We reported previously that a small molecule named CL-385319 could inhibit H5N1 influenza virus infection by targeting hemagglutinin, the envelope protein mediating virus entry. In the present study, a novel series of derivatives focused on the structural variation of CL-385319 were synthesized as specific inhibitors against the H5 subtype of influenza A viruses. These small molecules inhibited the low pH-induced conformational change of hemagglutinin, thereby blocking viral entry into host cells. Compound 11 was the most active inhibitor in this series with an IC50 of 0.22 mu M. The structure activity relationships analysis of these compounds showed that the 3-fluoro-5-(trifluoromethyl)benzamide moiety was very important for activity, and the -F group was a better substituent group than -CF3 group in the phenyl ring. The inhibitory activity was sensitive to the benzamide because the oxygen and hydrogen of the amide served as H-bond acceptor and donor, respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Ni-Catalyzed Direct Reductive Amidation via C–O Bond Cleavage
  作者：Arkaitz Correa、Ruben Martin

  DOI：10.1021/ja5029793

  日期：2014.5.21

  A novel Ni-catalyzed reductive amidation of C(sp(2))-O and C(sp(3))-O electrophiles with isocyanates is described. This umpolung reaction allows for an unconventional preparation of benzamides using simple starting materials and easy-to-handle Ni catalysts.