1-[3,5-bis(trifluoromethyl)phenyl]piperidine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-[3,5-bis(trifluoromethyl)phenyl]piperidine
• 化学式: C₁₃H₁₃F₆N
• 分子量: 297.243
• InChiKey: JVOUJTLHCCYVCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-piperidino-2-penten-4-one 、 六氟乙酰丙酮 在 溶剂黄146 作用下， 反应 4.0h， 以21%的产率得到1-[3,5-bis(trifluoromethyl)phenyl]piperidine
  参考文献：
  名称：

  Synthesis of functionalized m-bistrifluoromethylbenzenes via cyclocondensation of 1,1,1,5,5,5-hexafluoroacetylacetone with enamines

  摘要：

  The reaction of 1,1,1,5,5,5-hexafluoroacetylacetone with push-pull enamines having a methyl group at the alpha-position was investigated. It was found that the reaction is sensitive both to the structure of enamines and to reaction conditions. As a result, a set of bistrifluoromethyldialkylanilines and ethyl bistrifluoromethylsalicylate was prepared. Plausible mechanisms and factors influencing the course of the reaction are discussed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.075

文献信息

• Nickel-catalyzed cross-coupling aminations via high-throughput mechanochemistry enabled by resonant acoustic mixing
  作者：Alice Nanni、Deshen Kong、Chen Zhu、Magnus Rueping

  DOI：10.1039/d4gc01790k

  日期：——

  faster, and energy-efficient reactions, thereby reducing waste production and enhancing atom economy. Herein, we present a new nickel-catalyzed mechanochemical High Throughput Experimentation (HTE) amination protocol enabled by Resonant Acoustic Mixing (RAM). The developed C–N cross-coupling reactions avoid possible contamination, scaling-up challenges, and parallel reaction limitations by applying an

  近年来，机械化学已被公认为化学合成的高效、实用和可持续的替代方案。秉承绿色化学的原则，机械化学能够实现无溶剂、更快、节能的反应，从而减少废物产生并提高原子经济性。在此，我们提出了一种由共振声学混合（RAM）实现的新型镍催化机械化学高通量实验（HTE）胺化方案。通过应用加速筛选和优化方案，开发的 C-N 交叉偶联反应避免了可能的污染、放大挑战和平行反应限制。反应中溶剂量的减少和所需试剂的最少量突出了我们的方法相对于最常见的溶剂型反应的优势，符合可持续性和资源效率的原则。此外，机械化学方法证明了无需额外优化即可无缝扩展至数克规模，强调了其简化、环保和大规模工业生产的潜力。
• Iron-Catalyzed Oxidative C(3)–H Functionalization of Amines
  作者：Noriaki Takasu、Kounosuke Oisaki、Motomu Kanai

  DOI：10.1021/ol400568u

  日期：2013.4.19

  Fe-catalyzed direct dehydrogenative C(3)-functionalization of tertiary arylamines was developed via activation of the sp(3) C(3)-H bond. The reaction is applicable to both cyclic and acyclic amines. The key process is the catalytic desaturative enamine formation from tertiary amines and position-selective C-C bond formation (addition to nitro olefins) at the beta-carbon. Products can be converted to versatile and unique nitrogen-containing molecules.
• MATSUMOTO, KIYOSHI;UCHIDA, TAKANE;OKAMOTO, TADASHI;HASHIMOTO, SHIRO, CHEM. EXPRESS, 2,(1987) N 9, 551-554
  作者：MATSUMOTO, KIYOSHI、UCHIDA, TAKANE、OKAMOTO, TADASHI、HASHIMOTO, SHIRO

  DOI：——

  日期：——