3-(4-anisyl)-N-methylpropiolamide | 197231-97-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-anisyl)-N-methylpropiolamide
• 英文别名: 3-(4-methoxyphenyl)-N-methylprop-2-ynamide
• CAS: 197231-97-3
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: HBNYFODWBOKCRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

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-anisyl)-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72%的产率得到(E)-3-(4-methoxyphenyl)-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)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：

  4-碘苯甲醚 以76%的产率得到3-(4-anisyl)-N-methylpropiolamide
  参考文献：
  名称：

  Process of preparing substituted acrylamides

  摘要：

  本发明涉及一种制备丙烯酰胺的方法；其中，丙炔酰胺与活性芳香环反应，生成各种各样的丙烯酰胺。

  公开号：

  US05917038A1

文献信息

• 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。
• Palladium-catalyzed domino N-arylation/carbopalladation/C–H functionalization: three-component synthesis of 3-(diarylmethylene)oxindoles
  作者：Artur Pinto、Luc Neuville、Jieping Zhu

  DOI：10.1016/j.tetlet.2009.03.086

  日期：2009.7

  A palladium-catalyzed three-component synthesis of 3-(diarylmethylene)indolin-2-ones has been developed. A sequence of intermolecular N-arylation/intermolecular carbopalladation/C–H activation/C–C bond formation was realized in a one-pot fashion allowing the construction of one C–N bond and two C–C bonds by way of three distinct catalytic cycles.

  已经开发了3-（二芳基亚甲基）吲哚-2-酮的钯催化的三组分合成。以一锅方式实现了一系列分子间N-芳基化/分子间碳pal化/ C–H活化/ C–C键形成，从而允许通过三个不同的催化作用构建一个C–N键和两个C–C键周期。
• Palladium-Catalyzed Hydroarylation of Propiolamides. A Regio- and Stereocontrolled Method for Preparing 3,3-Diarylacrylamides
  作者：Lynne A. Hay、Thomas M. Koenig、Francis O. Ginah、James D. Copp、David Mitchell

  DOI：10.1021/jo980235h

  日期：1998.7.1

  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.
• 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