3-hydroxy-2-methylene-3-(pyridin-4-yl)propionamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-hydroxy-2-methylene-3-(pyridin-4-yl)propionamide
• 英文别名: 2-[Hydroxy(pyridin-4-yl)methyl]prop-2-enamide
• 化学式: C₉H₁₀N₂O₂
• 分子量: 178.191
• InChiKey: IZCTVGRNZWPJKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  76.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-hydroxy-2-methylene-3-(4-pyridinyl)propanenitrile 在 乙醛肟 、 palladium diacetate 、 三苯基膦 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以84%的产率得到3-hydroxy-2-methylene-3-(pyridin-4-yl)propionamide
  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

• Studying the Morita-Baylis-Hillman Reaction in Continuous Flow Using Packed Bed Reactors
  作者：Rasmus A. T. Verdier、Jesper H. Mikkelsen、Anders T. Lindhardt

  DOI：10.1021/acs.oprd.8b00298

  日期：2018.11.16

  Conditions for the Morita-Baylis-Hillman reaction were developed under continuous flow using a packed bed reactor carrying 4-(dimethylamino)pyridine immobilized on silica. High reaction rates were obtained, as the packed bed reactor mimics super-stoichiometric catalyst loadings for the passing reaction mixture. Catalyst deactivation was circumvented by avoiding acrylate esters as the reaction partners. The

  Morita-Baylis-Hillman反应的条件是使用载有固定在硅胶上的4-（二甲氨基）吡啶的填充床反应器在连续流动条件下开发的。由于填充床反应器模拟了通过的反应混合物的超化学计量催化剂负载，因此获得了高反应速率。通过避免丙烯酸酯作为反应伙伴来避免催化剂失活。开发的流程协议提供了所有所需的Morita-Baylis-Hillman产品，产率高达95％，典型保留时间仅为30至60分钟。一个实例证明了精确控制保留时间的必要性，其中仅在10分钟内即可达到最佳收率，同时超过了副产物的形成。最后，
• Successful Baylis−Hillman Reaction of Acrylamide with Aromatic Aldehydes
  作者：Chengzhi Yu、Longqin Hu

  DOI：10.1021/jo016004j

  日期：2002.1.1

  Acrylamide and aromatic aldehydes were found to undergo the Baylis-Hillman reaction at ambient temperature in an aqueous medium in the presence of a stoichiometric amount of base catalyst, DABCO, to give the corresponding 3-hydroxy-2-methylenepropionamides in 61-99% yield. A faster competing, but reverible, non-Baylis-Hillman reaction was initially observed under the conditions to form N-acylhemiaminals, which later disappeared, as the desired Baylis-Hillman adduct was formed as the major product over an extended period of time (12-48 h). This represents the first demonstration of the Baylis-Hillman reaction of aldehydes with acrylamides, which were thought to be inert under atmospheric pressure and at ambient temperature.
• 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。