1-(4-(2,2,2-trifluoroethyl)phenyl)ethan-1-one | 197312-65-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-(2,2,2-trifluoroethyl)phenyl)ethan-1-one
• 英文别名: 1-(4-(2,2,2-trifluoroethyl)phenyl)ethanone；4-(2,2,2-trifluoroethyl)acetophenone；1-[4-(2,2,2-Trifluoroethyl)phenyl]ethanone
• CAS: 197312-65-5
• 化学式: C₁₀H₉F₃O
• 分子量: 202.176
• InChiKey: VZKLOWIZQFIXSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(4-(2,2-difluorovinyl)phenyl)ethan-1-one 在 potassium fluoride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以90%的产率得到1-(4-(2,2,2-trifluoroethyl)phenyl)ethan-1-one
  参考文献：
  名称：

  A New Route for the Preparation of Substituted 2,2-Difluorostyrenes and a Convenient Route to Substituted (2,2,2-Trifluoroethyl)benzenes

  摘要：

  The (2,2-difluoroethenyl)zinc reagent II is coupled with aryl iodides or bromides in the presence of Pd(PPh3)(4) in DMF to give the corresponding 2,2-difluorostyrenes IV. The 4-substituted (tetrafluoroaryl)copper reagents are coupled with 2,2-difluoro-1-iodoethylene (I) to produce the corresponding styrene derivatives VII. Both methods provide good yields of the coupled products. These products react with wet KF in DMF or DMSO to form the (2,2,2-trifluoroethyl)benzene derivatives VIII in good yields.

  DOI：

  10.1021/jo971019w

文献信息

• Copper-Catalyzed Late-Stage Benzylic C(sp3)–H Trifluoromethylation
  作者：Haiwen Xiao、Zhonglin Liu、Haigen Shen、Benxiang Zhang、Lin Zhu、Chaozhong Li

  DOI：10.1016/j.chempr.2019.02.006

  日期：2019.4

  Direct trifluoromethylation of C(sp3)–H bonds, especially in late stages, remains a formidable challenge. Herein, we describe the copper-catalyzed benzylic C(sp3)–H trifluoromethylation. With Cu(I) or Cu(II) as the catalyst, (bpy)Zn(CF3)2 (bpy = 2,2′-bipyridine) as the CF3 source, and NFSI (or Selectfluor) as the oxidant, site-selective benzylic C(sp3)–H trifluoromethylation is successfully implemented

  C（sp 3）–H键的直接三氟甲基化，尤其是在后期阶段，仍然是一个艰巨的挑战。在这里，我们描述了铜催化的苄基C（sp 3）–H三氟甲基化。以Cu（I）或Cu（II）为催化剂，以（bpy）Zn（CF 3）2（bpy = 2,2'-联吡啶）作为CF 3源，以NFSI（或Selectfluor）作为氧化剂选择性苄基C（sp 3）–H三氟甲基化已在温和条件下成功高效地实施。该协议不仅展示了广泛的底物范围和广泛的官能团兼容性，而且还允许对天然产物或药物衍生物进行有效的后期C（sp 3）–H三氟甲基化。
• [EN] DIHYDROPYRAZOLOPYRIMIDINONE COMPOUNDS AS PDE2 INHIBITORS<br/>[FR] COMPOSÉS DIHYDROPYRAZOLOPYRIMIDINONE UTILISÉS EN TANT QU'EN TANT QU'INHIBITEURS DE PDE2
  申请人：MERCK SHARP & DOHME

  公开号：WO2016192083A1

  公开（公告）日：2016-12-08

  The present invention is directed to dihydropyrazolopyrimidinonecompounds of formula (I) which are useful as therapeutic agents for the treatment of central nervous system disorders associated with phosphodiesterase 2 (PDE2). The present invention also relates to the use of such compounds for treating neurological and psychiatric disorders, such as schizophrenia, psychosis, Parkinson's disease, Parkinson's disease dementia (PDD), or Huntington's disease, and those associated with striatal hypofunction or basal ganglia dysfunction.

  本发明涉及式(I)的二氢吡唑并嘧啶酮化合物，该化合物作为治疗与磷酸二酯酶2 (PDE2)相关的中枢神经系统障碍的治疗剂是有用的。本发明还涉及使用这些化合物来治疗神经和精神障碍，如精神分裂症、精神病、帕金森病、帕金森病痴呆（PDD）或亨廷顿病，以及与纹状体功能减退或基底神经节功能障碍相关的疾病。
• [EN] PYRAZOLYL PYRIMIDINONE COMPOUNDS AS PDE2 INHIBITORS<br/>[FR] COMPOSÉS PYRAZOLYLE PYRIMIDINONE UTILISÉS EN TANT QU'INHIBITEURS DE PDE2
  申请人：MERCK SHARP & DOHME

  公开号：WO2016154081A1

  公开（公告）日：2016-09-29

  The present invention is directed to pyrimidine carboxamide compounds of formula I which are useful as therapeutic agents for the treatment of central nervous system disorders associated with phosphodiesterase 2 (PDE2). The present invention also relates to the use of such compounds for treating neurological and psychiatric disorders, such as schizophrenia, psychosis, Parkinson's disease, Parkinson's disease dementia (PDD), or Huntington's disease, and those associated with striatal hypofunction or basal ganglia dysfunction.

  本发明涉及式I的嘧啶甲酰胺化合物，该化合物作为治疗与磷酸二酯酶2（PDE2）相关的中枢神经系统疾病的治疗剂是有用的。本发明还涉及使用这些化合物来治疗神经和精神疾病，如精神分裂症、精神病、帕金森病、帕金森病痴呆（PDD）或亨廷顿病，以及与纹状体功能减退或基底神经节功能障碍相关的疾病。
• Nickel‐Catalyzed Direct Trifluoroethylation of Aryl Iodides with 1,1,1‐Trifluoro‐2‐Iodoethane via Reductive Coupling
  作者：Han Li、Jie Sheng、Guang‐Xu Liao、Bing‐Bing Wu、Hui‐Qi Ni、Yan Li、Xi‐Sheng Wang

  DOI：10.1002/adsc.202000985

  日期：2020.12.8

  CF3CH2I has been developed, demonstrating high efficiency, excellent functional‐group compatibility, especially with large sterically hindered groups. The key to success is the combination of nickel with readily available nitrogen and phosphine ligands. The powerful potential of this strategy is further demonstrated by the late‐stage modification of several derived bioactive molecules.

  已经开发出了镍与工业原料CF 3 CH 2 I催化的碘代芳基碘的直接三氟乙基化反应，显示出高效率，出色的官能团相容性，特别是对于大的位阻基团。成功的关键是镍与现成的氮和膦配体的结合。几种衍生生物活性分子的后期修饰进一步证明了该策略的强大潜力。
• Switchable 2,2,2-Trifluoroethylation and<i>gem</i>-Difluorovinylation of Organoboronic Acids with 2,2,2-Trifluorodiazoethane
  作者：Guojiao Wu、Yifan Deng、Chaoqiang Wu、Xi Wang、Yan Zhang、Jianbo Wang

  DOI：10.1002/ejoc.201402597

  日期：2014.7

  The transition-metal-free 2,2,2-trifluoroethylation and gem-difluorovinylation of arylboronic acids were developed. By employing different reaction conditions, these transformations provide both (2,2,2-trifluoroethyl)arenes and gem-difluorovinylarenes from arylboronic acids and 2,2,2-trifluorodiazoethane. The operation is simple and scalable with good functional group tolerance.

  开发了无过渡金属的芳基硼酸的 2,2,2-三氟乙基化和偕二氟乙烯基化。通过采用不同的反应条件，这些转化由芳基硼酸和 2,2,2-三氟重氮乙烷提供 (2,2,2-三氟乙基) 芳烃和偕-二氟乙烯基芳烃。操作简单，可扩展，具有良好的官能团耐受性。