N,N-dimethyl-2-(hydroxymethyl)-acrylamide | 876908-50-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N-dimethyl-2-(hydroxymethyl)-acrylamide
• 英文别名: 2-Propenamide, 2-(hydroxymethyl)-N,N-dimethyl-；2-(hydroxymethyl)-N,N-dimethylprop-2-enamide
• CAS: 876908-50-8
• 化学式: C₆H₁₁NO₂
• 分子量: 129.159
• InChiKey: HIZROEXCAXJYBK-UHFFFAOYSA-N

物化性质

• 沸点：
  289.8±23.0 °C(Predicted)
• 密度：
  1.038±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-2-(hydroxymethyl)-acrylamide 在 四氢噻吩 、 三溴化磷 、 N,N-二甲基甲酰胺 、 sodium iodide 作用下， 以 乙醚 、 丙酮 、 乙腈 为溶剂， 反应 50.58h， 生成 cis-N,N-dimethyl-2-(3-phenyl-2-oxiranyl)-acrylamide
  参考文献：
  名称：

  A diastereoselective and concise synthesis of functionalised vinyl epoxides with a Morita–Baylis–Hillman backbone

  摘要：

  利用一种易于操作的硫叶立德环氧化方法，从易得的α-(溴甲基)丙烯酰胺衍生物出发，开发了一种高度非对映选择性的有机催化合成独特官能化的乙烯环氧化物的方法，该产物具有Morita-Baylis-Hillman骨架。本文讨论了对映选择性合成方法的首个结果。

  DOI：

  10.1039/b607040j
• 作为产物：
  描述：

  聚合甲醛 、 N,N-二甲基丙烯酰胺 在 三乙烯二胺 、 苯酚 作用下， 以 水 、 叔丁醇 为溶剂， 反应 72.0h， 以82%的产率得到N,N-dimethyl-2-(hydroxymethyl)-acrylamide
  参考文献：
  名称：

  A diastereoselective and concise synthesis of functionalised vinyl epoxides with a Morita–Baylis–Hillman backbone

  摘要：

  利用一种易于操作的硫叶立德环氧化方法，从易得的α-(溴甲基)丙烯酰胺衍生物出发，开发了一种高度非对映选择性的有机催化合成独特官能化的乙烯环氧化物的方法，该产物具有Morita-Baylis-Hillman骨架。本文讨论了对映选择性合成方法的首个结果。

  DOI：

  10.1039/b607040j

文献信息

• A stereodivergent synthesis of β-hydroxy-α-methylene lactones via vinyl epoxides
  作者：Marion Davoust、Frédéric Cantagrel、Patrick Metzner、Jean-François Brière

  DOI：10.1039/b802310g

  日期：——

  A catalytic diastereoselective sulfonium ylide epoxidation of aldehydes furnished original vinyl epoxides, having an MBH backbone. These highly functionalised building blocks were used for a formal synthesis of the antibiotic conocandin, and opened up a stereodivergent route towards β-hydroxy-α-methylene lactones, core units of naturally occurring compounds. Under acidic conditions, the oxiranes were mainly transformed, with moderate to good yields, into transβ-hydroxy-α-methylene lactones. On the other hand, a user-friendly palladium-catalysed CO2insertion and cyclisation sequence gave the cisβ-hydroxy-α-methylene lactone counterparts along with an interesting cis–trans equilibration of the π-allyl intermediates.

  一种催化性的非对映选择性硫镛叶立德环氧化反应，将醛转化为具有MBH骨架的原始乙烯基环氧化物。这些高度功能化的构建块被用于抗生素康索坎丁的正式合成，并开辟了一条向天然化合物核心单元——β-羟基-α-亚甲基内酯的立体发散性途径。在酸性条件下，环氧化物主要发生转化，产率从中等到良好，形成反式β-羟基-α-亚甲基内酯。另一方面，一种用户友好的钯催化CO2插入和环化序列，得到了顺式β-羟基-α-亚甲基内酯及其有趣的π-烯丙基中间体的顺-反平衡。
• Silanol based therapeutic payloads
  申请人：BlinkBio, Inc.

  公开号：US10716801B2

  公开（公告）日：2020-07-21

  Described herein in part are silanol based therapeutic payloads comprising a silanol terminus, a divalent spacer moiety, and a drug moiety capable of effecting a target cell or tissue.

  本文部分描述的是基于硅烷醇的治疗有效载荷，包括硅烷醇末端、二价间隔物和能够作用于靶细胞或组织的药物分子。
• Synthesis, in vitro, and in vivo evaluation of novel functionalized quaternary ammonium curcuminoids as potential anti-cancer agents
  作者：Lucas N. Solano、Grady L. Nelson、Conor T. Ronayne、Erica A. Lueth、Melissa A. Foxley、Sravan K. Jonnalagadda、Shirisha Gurrapu、Venkatram R. Mereddy

  DOI：10.1016/j.bmcl.2015.10.061

  日期：2015.12

  Novel functionalized quaternary ammonium curcuminoids have been synthesized from piperazinyl curcuminoids and Baylis-Hillman reaction derived allyl bromides. These molecules are found to be highly water soluble with increased cytotoxicity compared to native curcumin against three cancer cell lines MIAPaCa-2, MDA-MB-231, and 4T1. Preliminary in vivo toxicity evaluation of a representative curcuminoid 5a in healthy mice indicates that this molecule is well tolerated based on normal body weight gains compared to control group. Furthermore, the efficacy of 5a has been tested in a pancreatic cancer xenograft model of MIAPaCa-2 and has been found to exhibit good tumor growth inhibition as a single agent and also in combination with clinical pancreatic cancer drug gemcitabine. (C) 2015 Elsevier Ltd. All rights reserved.
• A diastereoselective and concise synthesis of functionalised vinyl epoxides with a Morita–Baylis–Hillman backbone
  作者：Marion Davoust、Jean-François Brière、Patrick Metzner

  DOI：10.1039/b607040j

  日期：——

  A highly diastereoselective organocatalytic synthesis of unique functionalised vinyl epoxides, displaying a Morita–Baylis–Hillman backbone, has been developed by means of an user friendly sulfonium ylide epoxidation of aldehydes from a readily available α-(bromomethyl)acrylamide derivative. The first result in the asymmetric version is discussed.

  利用一种易于操作的硫叶立德环氧化方法，从易得的α-(溴甲基)丙烯酰胺衍生物出发，开发了一种高度非对映选择性的有机催化合成独特官能化的乙烯环氧化物的方法，该产物具有Morita-Baylis-Hillman骨架。本文讨论了对映选择性合成方法的首个结果。
• Intermolecular Aminoallylation of Alkenes Using Allyl-Oxyphthalimide Derivatives: A Case Study in Radical Polarity Effects
  作者：Samuel W. Lardy、Valerie A. Schmidt

  DOI：10.1002/ejoc.201901071

  日期：2019.10.31

  This work describes the essential radical polarity effects manifested in pursuit of a group transfer radical addition to achieve alkene aminoallylation. Each open shell intermediate along the proposed mechanistic pathway is steered to preferentially react with only one reagent.

  这项工作描述了在追求基团转移自由基加成以实现烯烃氨基烯丙基化时表现出的基本自由基极性效应。沿拟议的机理途径的每个开壳中间体都经过导向，仅与一种试剂优先发生反应。