N-(2-(trifluoromethyl)benzyl)pivalamide | 304664-21-9

• 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-(2-(trifluoromethyl)benzyl)pivalamide
• 英文别名: 2,2-Dimethyl-N-(2-trifluoromethyl-benzyl)-propionamide；2,2-dimethyl-N-[[2-(trifluoromethyl)phenyl]methyl]propanamide
• CAS: 304664-21-9
• 化学式: C₁₃H₁₆F₃NO
• mdl: MFCD01325792
• 分子量: 259.271
• InChiKey: MJALYHCWBYHLDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-(trifluoromethyl)benzyl)pivalamide 在 potassium pyrosulfate 、 palladium diacetate 、 potassium carbonate 作用下， 以 2,2,2-三氟乙醇 、 乙腈 为溶剂， 反应 24.0h， 生成 3,3-dimethyl-1-(2-(trifluoromethyl)benzyl)azetidin-2-one
  参考文献：
  名称：

  Palladium-Catalyzed β-Mesylation of Simple Amide via Primary sp³ C–H Activation

  摘要：

  A beta-mesylation of primary sp(3) C-H bonds from simple amides with methanesulfonic anhydride; (Ms2O) has been established successfully A 80 degrees C in a Pd(OAc)(2) (catalyst)/K2S2O8 (oxidant)CF3CH2OH (solvent) system. These amide substrates involve N-monosubstituted linear,, branch, or cyclic alkanes, and electron-deficient benzyl compounds. The beta-mesylated amide products can be converted easily to beta-fluoroamideS or beta-lactams through inter- or intramolecular S(N)2 processes.

  DOI：

  10.1021/acs.orglett.7b00536
• 作为产物：
  描述：

  2-(三氟甲基)苄胺 、 三甲基乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以64%的产率得到N-(2-(trifluoromethyl)benzyl)pivalamide
  参考文献：
  名称：

  由单一阴离子配体实现的苄胺，苯乙胺和苯丙胺衍生的酰胺的亚选择性CH硼化

  摘要：

  巧妙的定位：结合有远端阴离子磺酸盐基团的联吡啶配体可将铱催化的硼化反应引导至一系列含酰胺芳烃的间位。提出该选择性是氢键相互作用的结果，该氢键相互作用将铱金属中心正确定位在关键的CH活化中。

  DOI：

  10.1002/anie.201708967

文献信息

• NOVEL HETEROCYCLIC COMPOUNDS
  申请人：Jain Rajesh

  公开号：US20100311732A1

  公开（公告）日：2010-12-09

  The present invention relates to novel compounds of Formula I, their pharmaceutically acceptable derivatives, tautomeric forms, stereoisomers including R and S isomers, polymorphs, prodrugs, metabolites, salts or solvates thereof. The invention also relates to the processes for the synthesis of novel compounds of Formula I, their pharmaceutically acceptable derivatives, tautomeric forms, stereoisomers, polymorphs, prodrugs, metabolites, salts or solvates thereof. The present invention also provides pharmaceutical compositions comprising compounds of Formula I and methods of treating or preventing one or more conditions that may be regulated or normalized via inhibition of dipeptidyl peptidase IV (DPP-IV).

  本发明涉及一种新型I式化合物，其药学上可接受的衍生物、互变异构体、立体异构体（包括R和S异构体）、多晶形、前药、代谢物、盐或溶剂化物。本发明还涉及制备新型I式化合物、其药学上可接受的衍生物、互变异构体、立体异构体、多晶形、前药、代谢物、盐或溶剂化物的方法。本发明还提供了包含I式化合物的制药组合物和通过抑制二肽基肽酶IV（DPP-IV）来治疗或预防可能通过调节或规范的一种或多种情况的方法。
• Palladium-Catalyzed β-Acyloxylation of Simple Amide <i>via</i> sp³ C–H Activation
  作者：Lihong Zhou、Wenjun Lu

  DOI：10.1021/ol403393w

  日期：2014.1.17

  beta-Acylcoxy amides are prepared in moderate to high yields by palladium-catalyzed acyloxylation of primary sp(3) C-H bonds from simple amides without any special directing group. A catalytic system of Pd(OAc)(2)/CF3CO2H/K2S2O8 is available to various amides with N-substituted by linear alkanes, cyclic alkanes, and electron-deficient benzyl compounds in this reaction. Acyloxylated products could be transformed easily to the corresponding beta-hydroxy amides.
• Palladium-Catalyzed β-Arylation of Amide via Primary sp³C–H Activation
  作者：Ren Zhao、Wenjun Lu

  DOI：10.1021/acs.organomet.8b00325

  日期：2018.7.9

  A beta-arylation of primary sp(3)C-H bonds on simple amides such as pivalamides with aryl iodides/ CF3CO2Ag has been established successfully at 120 degrees C in a Pd(OAc)(2) (catalyst)/CF3CH2OH (solvent) system. Pivalamides including (BuCONH2)-Bu-t, (BuCONHR)-Bu-t, and (BuCONR2)-Bu-t undergo the arylations smoothly to afford beta-aryl pivalamides in moderate to good yields. Various aryl iodides are available bearing either electron-donating or electron-withdrawing substituted groups in the coupling reactions.
• US8455479B2
  申请人：——

  公开号：US8455479B2

  公开（公告）日：2013-06-04
• Palladium-Catalyzed β-Mesylation of Simple Amide via Primary sp³ C–H Activation
  作者：Ren Zhao、Wenjun Lu

  DOI：10.1021/acs.orglett.7b00536

  日期：2017.4.7

  A beta-mesylation of primary sp(3) C-H bonds from simple amides with methanesulfonic anhydride; (Ms2O) has been established successfully A 80 degrees C in a Pd(OAc)(2) (catalyst)/K2S2O8 (oxidant)CF3CH2OH (solvent) system. These amide substrates involve N-monosubstituted linear,, branch, or cyclic alkanes, and electron-deficient benzyl compounds. The beta-mesylated amide products can be converted easily to beta-fluoroamideS or beta-lactams through inter- or intramolecular S(N)2 processes.