2-[hydroxy(2-naphthyl)methyl]acrylamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[hydroxy(2-naphthyl)methyl]acrylamide
• 英文别名: 2-[Hydroxy(naphthalen-2-yl)methyl]prop-2-enamide
• 化学式: C₁₄H₁₃NO₂
• 分子量: 227.263
• InChiKey: PHBKMLKDFZBRIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-hydroxy-2-methylene-3-(2-naphthyl)propanenitrile 在 乙醛肟 、 palladium diacetate 、 三苯基膦 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以75%的产率得到2-[hydroxy(2-naphthyl)methyl]acrylamide
  参考文献：
  名称：

  丙烯酰胺Baylis-Hillman加合物的有效合成：Pd催化的丙烯腈Baylis-Hillman加合物的水合

  摘要：

  开发了一种有效的钯催化两步法合成丙烯酰胺的Baylis-Hillman加合物。该方法涉及丙烯腈Baylis-Hillman加合物的制备以及乙二醛与乙醛肟的Pd催化水合反应。

  DOI：

  10.1016/j.tetlet.2009.08.127

文献信息

• Acrylamide in the Baylis−Hillman Reaction:  Expanded Reaction Scope and the Unexpected Superiority of DABCO over More Basic Tertiary Amine Catalysts
  作者：Cornelia Faltin、Eimear M. Fleming、Stephen J. Connon

  DOI：10.1021/jo0490907

  日期：2004.9.1

  DMAP, DBU, and quinuclidine efficiently promote novel hydroalkoxylation reactions of acrylamide in primary alcohol solvents. DABCO is a comparatively poor hydroalkoxylation promoter and can effect clean, selective Baylis-Hillman reactions between acrylamide and aldehydes in alcoholic/aqueous media in which more basic nucleophilic catalysts promote hydroalkoxylation preferentially. Optimization of the reaction conditions has allowed acrylamide to be reacted with a range of aromatic aldehydes in moderate to excellent yields, including the first examples involving deactivated, electron-rich substrates such as p-tolualdehyde and o-anisaldehyde.
• An efficient synthesis of Baylis–Hillman adducts of acrylamide: Pd-catalyzed hydration of Baylis–Hillman adducts of acrylonitrile
  作者：Eun Sun Kim、Hyun Seung Lee、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2009.08.127

  日期：2009.11

  An efficient palladium-catalyzed two-step protocol for the synthesis of Baylis–Hillman adducts of acrylamide was developed. The method involved the preparation of Baylis–Hillman adducts of acrylonitrile and a Pd-catalyzed hydration of nitrile with acetaldoxime.

  开发了一种有效的钯催化两步法合成丙烯酰胺的Baylis-Hillman加合物。该方法涉及丙烯腈Baylis-Hillman加合物的制备以及乙二醛与乙醛肟的Pd催化水合反应。