N-phenethyl-3,5-bis(trifluoromethyl)benzamide | 135726-93-1

• 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-phenethyl-3,5-bis(trifluoromethyl)benzamide
• 英文别名: N-(2-phenylethyl)-3,5-bis(trifluoromethyl)benzamide
• CAS: 135726-93-1
• 化学式: C₁₇H₁₃F₆NO
• 分子量: 361.287
• InChiKey: NXEPBOJQJAAFAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-phenethyl-3,5-bis(trifluoromethyl)benzamide 在 Selectfluor 、 lithium bromide 、 yttrium(III) trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以42%的产率得到2-(3,5-bis(trifluoromethyl)phenyl)-5-phenyl-4,5-dihydrooxazole
  参考文献：
  名称：

  可见光溴化物催化通过 Csp3-H 官能化合成恶唑啉、吡咯烷和二氢恶嗪

  摘要：

  此处描述了催化苄基 C sp 3 –H 功能化协议。这种可见光介导的过程集中在利用溴化物催化剂和氧化剂来生成以氮 (N) 为中心的自由基，用于位点选择性氢原子转移 (HAT) 过程。这种策略使依赖酰胺身份的许多 N-杂环的非常规合成成为可能。我们还发现了 C sp 3 -H 键立体化学分化的亲核依赖性动力学分辨率，这使得顺式和反式恶唑啉的立体选择性合成成为可能。

  DOI：

  10.1039/d1cc04588a
• 作为产物：
  描述：

  3,5-双三氟甲基苯甲酸 、 2-苯乙胺 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以87%的产率得到N-phenethyl-3,5-bis(trifluoromethyl)benzamide
  参考文献：
  名称：

  Design, synthesis and structure–activity relationship of novel inhibitors against H5N1 hemagglutinin-mediated membrane fusion

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2012.08.041

文献信息

• Formal Nucleophilic Substitution of Bromocyclopropanes with Amides en route to Conformationally Constrained β-Amino Acid Derivatives
  作者：Anthony R. Prosser、Joseph E. Banning、Marina Rubina、Michael Rubin

  DOI：10.1021/ol101228k

  日期：2010.9.17

  A chemo- and diastereoselective protocol for the formal nucleophilic substitution of 2-bromocyclopropylcarboxamides with secondary amides is described. This method allows for convergent and highly selective synthesis of trans-β-aminocyclopropane carboxylic acid derivatives.

  描述了用仲酰胺对2-溴环丙基羧酰胺进行正式亲核取代的化学和非对映选择性方案。该方法允许反式-β-氨基环丙烷羧酸衍生物的收敛和高度选择性的合成。
• Formal Substitution of Bromocyclopropanes with Nitrogen Nucleophiles
  作者：Joseph E. Banning、Jacob Gentillon、Pavel G. Ryabchuk、Anthony R. Prosser、Andrew Rogers、Andrew Edwards、Andrew Holtzen、Ivan A. Babkov、Marina Rubina、Michael Rubin

  DOI：10.1021/jo4011798

  日期：2013.8.2

  A highly chemo- and diastereoselective protocol toward amino-substituted donor acceptor cyclopropanes via the formal nucleophilic displacement in bromocyclopropanes is described. A wide range of N-nucleophiles, including carboxamides, sulfonamides, azoles, and anilines, can be efficiently employed in this transformation, providing expeditious access to stereochemically defined and densely functionalized cydopropylamine derivatives.
• Visible light bromide catalysis for oxazoline, pyrrolidine, and dihydrooxazine syntheses <i>via</i> C_sp³–H functionalizations
  作者：Navdeep Kaur、Elizabeth C. Ziegelmeyer、Olutayo N. Farinde、Jonathon T. Truong、Michelle M. Huynh、Wei Li

  DOI：10.1039/d1cc04588a

  日期：——

  (N)-centered radical for a site-selective hydrogen atom transfer (HAT) process. This strategy enabled the unconventional syntheses of a number of N-heterocycles dependent on the amide identity. We also discovered a nucleophilicity-dependent kinetic resolution for stereochemical differentiation of Csp3–H bonds that enabled the stereoselective synthesis of cis- and trans-oxazolines.

  此处描述了催化苄基 C sp 3 –H 功能化协议。这种可见光介导的过程集中在利用溴化物催化剂和氧化剂来生成以氮 (N) 为中心的自由基，用于位点选择性氢原子转移 (HAT) 过程。这种策略使依赖酰胺身份的许多 N-杂环的非常规合成成为可能。我们还发现了 C sp 3 -H 键立体化学分化的亲核依赖性动力学分辨率，这使得顺式和反式恶唑啉的立体选择性合成成为可能。
• 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.