3-(4-α,α,α-trifluoromethylphenyl)-N-methylpropiolamide | 197231-98-4

• 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: 3-(4-α,α,α-trifluoromethylphenyl)-N-methylpropiolamide
• 英文别名: N-Methyl-3-[4-(trifluoromethyl)phenyl]-2-propynamide；N-methyl-3-[4-(trifluoromethyl)phenyl]prop-2-ynamide
• CAS: 197231-98-4
• 化学式: C₁₁H₈F₃NO
• 分子量: 227.186
• InChiKey: MBOVEQOLDHYEAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  1-频哪醇-2-(1,8)萘二胺联硼酸酯 、 3-(4-α,α,α-trifluoromethylphenyl)-N-methylpropiolamide 在 15-冠醚-5 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以71%的产率得到(E)-N-methyl-2-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(4-(trifluoromethyl)phenyl)acrylamide
  参考文献：
  名称：

  底物辅助，混合二硼烷的无过渡金属烷基化硼酸酯：对反式1,2-乙烯基二硼酸酯的区域和立体选择。

  摘要：

  本文介绍了使用不对称的频哪醇-1,8-二氨基萘萘二硼（pinBBdan）对炔酰胺进行底物辅助的硼氢化反应。无过渡金属的反应以区域选择性和立体选择性的方式进行，从而以高至优异的收率独家提供反式乙烯基二硼酸酯。值得注意的是，Bdan和Bpin分别安装在α-和β-碳原子上。

  DOI：

  10.1002/anie.201700946
• 作为产物：
  描述：

  N-methyl-2-propynamide 、 4-碘三氟甲苯 在 copper(l) iodide 、 bis(triphenylphosphine) palladium (Il) acetate 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 以85%的产率得到3-(4-α,α,α-trifluoromethylphenyl)-N-methylpropiolamide
  参考文献：
  名称：

  Palladium-Catalyzed Hydroarylation of Propiolamides. A Regio- and Stereocontrolled Method for Preparing 3,3-Diarylacrylamides

  摘要：

  A general regio- and stereoselective synthesis of 3,3-diarylacrylamides is reported. Palladium-catalyzed coupling reactions of propiolamides with aryl halides provide arylpropiolamides. A subsequent hydroarylation reaction of these arylpropiolamides with aryl halides, catalytic palladium, an amine base, and formic acid in refluxing ethyl acetate provides 3,3-diarylacrylamides regio- and stereoselectively. The unique stereo- and regiocontrol is presumed to proceed through careful reaction parameters that allow intramolecular coordination of the propiolamide amide functionality to the transient palladium-alkyne complex. Palladium-catalyzed hydroarylation of propiolamides has not been studied; however, preliminary results from related systems suggest that regioselective addition can be achieved. The methodology as a synthesis tool is demonstrated in an efficient route to previously difficult-to-prepare potent, benzimidazole antiviral targets. In addition, the synthesis scope is explored where, by judicious choice of reaction sequence and aryl iodide, either the Z- or E-geometric isomer of a given pair of 3,3-diarylacrylamides is independently prepared.

  DOI：

  10.1021/jo980235h

文献信息

• <i>trans</i>-Hydroboration of Propiolamides: Access to Primary and Secondary (<i>E</i>)-β-Borylacrylamides
  作者：R. Justin Grams、Russell G. Fritzemeier、Carla Slebodnick、Webster L. Santos

  DOI：10.1021/acs.orglett.9b02408

  日期：2019.9.6

  A base-mediated trans-hydroboration of propiolamides that provides access to previously elusive primary and secondary (E)-β-borylacrylamide products has been developed. In the presence of n-butyllithium and pinacolborane, complete regioselectivity and stereoselectivity is observed, affording the corresponding vinylboronate products in up to 91% yield. A wide variety of primary and secondary amides

  已经开发了丙酰胺的碱介导的反硼氢化，其提供了先前难以捉摸的伯和仲（E）-β-硼基丙烯酰胺产品的途径。在正丁基锂和频哪醇硼烷的存在下，观察到完全的区域选择性和立体选择性，从而以高达91％的产率提供了相应的乙烯基硼酸酯产物。各种各样的伯酰胺和仲酰胺可作为这种转化的有效底物。讨论了一种可能的反应机制，其中涉及底物辅助的活化和关键的分子内环化。
• Brønsted Base‐Mediated Regio‐ and Stereoselective <i>trans‐</i> Silaboration of Propargylamides: Access to 1,2‐Vinylborasilanes
  作者：Russell Fritzemeier、Webster L. Santos

  DOI：10.1002/chem.201703774

  日期：2017.11.2

  A facile method for the preparation of β‐boryl‐α‐silyl aryl acrylamides using phenyllithium, dimethylphenylsilylpinacolborane, and propargylamides is reported. A key feature of this transition metal‐free reaction is the Brønsted base deprotonation of aryl secondary propargylamide to produce a Lewis base that activates the B−Si bond, which is followed by a sequential intramolecular α‐silylation‐trans‐β‐borylation

  报道了一种使用苯基锂，二甲基苯基甲硅烷基萘烷硼烷和炔丙基酰胺制备β-硼基-α-甲硅烷基芳基丙烯酰胺的简便方法。该无过渡金属反应的关键特征是芳基仲炔丙基酰胺的布朗斯台德碱去质子化反应产生路易斯碱，该碱激活了B-Si键，随后依次进行分子内的α-甲硅烷基化-反式-β-硼化。反应以完全的区域和立体选择性进行。各种各样的N-和芳基取代的炔丙基酰胺可以高收率提供反式1,2-乙烯基硼硅烷。邻位硼硅烷产物经历各种随后的化学选择性转化。
• A regio- and stereocontrolled method for preparing 3,3-diarylacrylamides
  作者：Lynne A. Hay、David Mitchell

  DOI：10.1016/s0040-4039(97)01528-1

  日期：1997.9

  Palladium-catalyzed hydroarylation of acetylenes provides regio- and stereodefined olefins. This methodology has been extended to arylpropiolamides where 3,3-diarylaclylamides are prepared stereospecifically. In an independent fashion, both the E- and Z-isomers were prepared by judicious choice of arylpropiolamide preparation and the palladium catalyzed hydroarylation reaction. (C) 1997 Elsevier Science Ltd.
• PROCESS OF PREPARING SUBSTITUTED ACRYLAMIDES
  申请人：ELI LILLY AND COMPANY

  公开号：EP0944581A1

  公开（公告）日：1999-09-29
• EP0944581A4
  申请人：——

  公开号：EP0944581A4

  公开（公告）日：2004-09-08