1-piperidinyl[4-(trifluoromethoxy)phenyl]methanone | 1215169-57-5

• 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: 1-piperidinyl[4-(trifluoromethoxy)phenyl]methanone
• 英文别名: Piperidin-1-yl-[4-(trifluoromethoxy)phenyl]methanone
• CAS: 1215169-57-5
• 化学式: C₁₃H₁₄F₃NO₂
• 分子量: 273.255
• InChiKey: RTPOPRWETZBFNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-甲氧基噻吩 、 1-piperidinyl[4-(trifluoromethoxy)phenyl]methanone 在 正丁基锂 作用下， 以52%的产率得到(4-trifluoromethoxyphenyl)-(3-methoxythiophen-2-yl)-methanone
  参考文献：
  名称：

  Synthesis of isotopically labelled SGLT inhibitors and their metabolites

  摘要：

  Isotopically labelled analogues of two structurally very similar SGLT inhibitors AVE2268 (1a) and AVE8887 (1b) have been synthesized by various routes. The radioactive labelled [C-14]-AVE2268 was prepared in five steps including a Friedel-Crafts acylation as the key step for the C-14-label introduction. For [C-14]-AVE8887 the same synthetic approach was not successful and therefore an alternative thiophene metallation/Weinreb amide sequence was developed. This pathway was also applied to obtain stable isotopically labelled analogues of both AVE2268 and AVE8887. Finally, the synthesis of two metabolites, sulfate 12 and glucuronide 13 were achieved by applying interesting protecting group and oxidation strategies. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.12.003
• 作为产物：
  描述：

  哌啶 、 4-三氟甲氧基苯甲酸 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以88%的产率得到1-piperidinyl[4-(trifluoromethoxy)phenyl]methanone
  参考文献：
  名称：

  Synthesis of a Combinatorial Library of Amides and Its Evaluation against the Fall Armyworm, Spodoptera frugiperda

  摘要：

  The fall armyworm Spodoptera frugiperda is a polyphagous pest that causes important damage in different regions of America and mainly affects corn crops in both tropical and subtropical areas. Currently, control relies on both transgenic plants and/or chemical pesticides. In this work we describe the preparation of an indexed combinatorial library of amides and its toxic effect by contact against S. frugiperda . (E)-1-(1-Piperidinyl)-3-[4-(trifluoromethoxy)phenyl]-2-propen-1-one was the most active compound with an LD(50) = 0.793 mu g mg(-1) of larva. This amide was also evaluated by ingestion and at the lowest concentration (1 mg kg(-1)) achieved 83.3% mortality.

  DOI：

  10.1021/jf104903t

文献信息

• Reactivity Umpolung of Tertiary Amide Enabled by Catalytic Reductive Stannylation
  作者：Qiu Shi、Wenbo H. Liu

  DOI：10.1002/anie.202309567

  日期：2023.9.11

  Amide carbonyl group usually serves as the electrophile, which can react with various nucleophiles. The current work shows a process to achieve the umpolung reactivity of tertiary amide carbonyl group. By leveraging this strategy, tertiary amide can react with a wide range of electrophiles to produce complex amines.

  酰胺羰基通常作为亲电子试剂，可以与各种亲核试剂发生反应。目前的工作展示了一种实现叔酰胺羰基的反极性反应性的方法。通过利用这种策略，叔酰胺可以与多种亲电子试剂反应生成复杂的胺。
• Synthesis of isotopically labelled SGLT inhibitors and their metabolites
  作者：Volker Derdau、Thorsten Fey、Jens Atzrodt

  DOI：10.1016/j.tet.2009.12.003

  日期：2010.2

  Isotopically labelled analogues of two structurally very similar SGLT inhibitors AVE2268 (1a) and AVE8887 (1b) have been synthesized by various routes. The radioactive labelled [C-14]-AVE2268 was prepared in five steps including a Friedel-Crafts acylation as the key step for the C-14-label introduction. For [C-14]-AVE8887 the same synthetic approach was not successful and therefore an alternative thiophene metallation/Weinreb amide sequence was developed. This pathway was also applied to obtain stable isotopically labelled analogues of both AVE2268 and AVE8887. Finally, the synthesis of two metabolites, sulfate 12 and glucuronide 13 were achieved by applying interesting protecting group and oxidation strategies. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of a Combinatorial Library of Amides and Its Evaluation against the Fall Armyworm, Spodoptera frugiperda
  作者：Thais C. Castral、Andreia P. Matos、Julia L. Monteiro、Fernanda M. Araujo、Tatiani M. Bondancia、Luciane G. Batista-Pereira、João B. Fernandes、Paulo C. Vieira、M. Fatima G. F. da Silva、Arlene G. Corrêa

  DOI：10.1021/jf104903t

  日期：2011.5.11

  The fall armyworm Spodoptera frugiperda is a polyphagous pest that causes important damage in different regions of America and mainly affects corn crops in both tropical and subtropical areas. Currently, control relies on both transgenic plants and/or chemical pesticides. In this work we describe the preparation of an indexed combinatorial library of amides and its toxic effect by contact against S. frugiperda . (E)-1-(1-Piperidinyl)-3-[4-(trifluoromethoxy)phenyl]-2-propen-1-one was the most active compound with an LD(50) = 0.793 mu g mg(-1) of larva. This amide was also evaluated by ingestion and at the lowest concentration (1 mg kg(-1)) achieved 83.3% mortality.