N-benzyl-2-hydroxy-2-methylpropanamide | 103853-77-6

• 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: N-benzyl-2-hydroxy-2-methylpropanamide
• CAS: 103853-77-6
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: JIUULHWOZXJLFA-UHFFFAOYSA-N

物化性质

• 熔点：
  60-61 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  393.2±35.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-2-hydroxy-2-methylpropanamide 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.0h， 生成 3-Benzyl-5,5-dimethyl-2,2-dioxooxathiazolidin-4-one
  参考文献：
  名称：

  Synthesis and anticonvulsant activity of bioisosteres of trimethadione, N-derivative-1,2,3-oxathiazolidine-4-one-2,2-dioxides from α-hydroxyamides

  摘要：

  The synthesis and anticonvulsant activity of novel heterocycles N-derivative-1,2,3-oxathiazolidine-4-one-2,2-dioxides, bioisosteres of trimethadione (TMD, oxazolidine-2,4-dione) and phenytoin (PHE), are described. TMD is an anticonvulsant drug widely used against absences seizures in the early 80's and PHE is an antiepileptic drug with a wide spectrum activity. The intermediates of synthesis of N-derivative-1,2,3-oxathiazolidine-4-one-2,2-dioxides, alpha-hydroxyamides, were obtained using microwave assisted synthesis. Anticonvulsant screening was performed in mice after intraperitoneal administration in the maximal electroshock seizure test (MES) and subcutaneous pentylenetetrazole seizures test (scPTZ). These new compounds showed a wide spectrum activity and were no neurotoxic in the RotoRod test. alpha-Hydroxyamides and N-derivative-1,2,3-oxathiazolidine-4-one-2,2-dioxides were 3-4700 times more potent than valproic acid in the MES test. Quantification of anticonvulsant protection was calculated (ED50) for the most active candidates; alpha-hydroxyamides 3a-c and 3e, and N-derivative-oxathiazolidine-4-one-2,2-dioxides 5a-c with ED50 values of 9.1, 53.9, 44.6, 25.2, 15.1, 91.1 and 0.06 mg/kg, respectively, in the MES test. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.033
• 作为产物：
  描述：

  N-苄基-2-溴-2-甲基丙酰胺 在 水 、 silver(l) oxide 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以90.5%的产率得到N-benzyl-2-hydroxy-2-methylpropanamide
  参考文献：
  名称：

  溴酰胺作为合成α-羟基和α-烷氧基衍生物的原料

  摘要：

  摘要 氧化银促进 α - 溴甲酰胺的 2 位溴被羟基或烷氧基取代。

  DOI：

  10.1080/00397919408019046

文献信息

• Primary Alkylboronic Acids as Highly Active Catalysts for the Dehydrative Amide Condensation of α-Hydroxycarboxylic Acids
  作者：Risa Yamashita、Akira Sakakura、Kazuaki Ishihara

  DOI：10.1021/ol401537f

  日期：2013.7.19

  Primary alkylboronic acids such as methylboronic acid and butylboronic acid are highly active catalysts for the dehydrative amide condensation of α-hydroxycarboxylic acids. The catalytic activities of these primary alkylboronic acids are much higher than those of the previously reported arylboronic acids. The present method was easily applied to a large-scale synthesis, and 14 g of an amide was obtained

  伯烷基硼酸，例如甲基硼酸和丁基硼酸，是用于α-羟基羧酸脱水酰胺缩合的高活性催化剂。这些伯烷基硼酸的催化活性比以前报道的芳基硼酸的催化活性高得多。本方法容易用于大规模合成，并且在单个反应中获得14g酰胺。
• On DABAL-Me3 promoted formation of amides
  作者：Nathalie Dubois、Daniel Glynn、Thomas McInally、Barrie Rhodes、Simon Woodward、Derek J. Irvine、Chris Dodds

  DOI：10.1016/j.tet.2013.08.062

  日期：2013.11

  acids with primary and secondary amines under a variety of conditions (reflux, sealed tube, microwave) has been compared for a significant range of coupling partners of relevance to the preparation of amides of interest in pharmaceutical chemistry. Commercial microwave reactors promote the fastest couplings and allow the use of significantly sterically hindered amines (primary and secondary) and carboxylic

  的范围和DABAL-ME的效用3个甲基酯和游离羧酸与在各种条件下伯和仲胺（回流，密封管，微波）的联接器相比已经用于显著范围耦合相关的伙伴制备的医药化学中感兴趣的酰胺类化合物。商业微波反应器促进最快的偶联，并允许使用空间位阻显着的胺（伯胺和仲胺）和羧酸衍生物。已显示微波能量对反应系统的影响通常与热效应（过压和过热）有关。
• Highly Efficient DMSO‐Promoted α‐Hydrolysis of α‐Halohydroxamates under Mild Conditions
  作者：Chang Yoon Lee、Sung‐Gon Kim

  DOI：10.1002/ejoc.202100088

  日期：2021.3.12

  A novel and efficient method for the nucleophilic α‐hydrolysis of α‐halohydroxamates under metal‐free conditions was achieved. The simple and readily available dimethyl sulfoxide (DMSO) was used as a catalyst, while water served as the nucleophile and oxygen source. This method was successfully employed in the synthesis of secondary α‐hydroxy‐α‐alkyl and α‐hydroxy‐α‐arylhydroxamates as well as tertiary

  实现了一种新颖且有效的无金属条件下α-卤代异羟肟酸酯亲核α-水解的方法。简单易用的二甲基亚砜（DMSO）用作催化剂，而水用作亲核试剂和氧气源。该方法成功地用于合成仲α-羟基-α-烷基和α-羟基-α-芳基异羟肟酸酯以及叔α-羟基-α-二烷基异羟肟酸酯。
• MCF-supported boronic acids as efficient catalysts for direct amide condensation of carboxylic acids and amines
  作者：Liuqun Gu、Jaehong Lim、Jian Liang Cheong、Su Seong Lee

  DOI：10.1039/c4cc01148a

  日期：——

  For efficient direct amide condensations, a new class of catalysts are developed by immobilizing boronic acids on mesocellular siliceous foam. Associated with their large pores, the microenvironments surrounding the immobilized active species greatly influence the catalytic activity. The fluoroalkyl moieties on the silica surface significantly enhance the catalytic performance along with easy recovery

  为了有效地直接进行酰胺缩合，通过将硼酸固定在介孔硅质泡沫上，开发了新型的催化剂。与它们的大孔相关联，固定化活性物质周围的微环境极大地影响了催化活性。二氧化硅表面上的氟代烷基部分显着增强了催化性能，并易于回收和再利用。该方法提出了优化各种类型的二氧化硅负载的催化剂的潜在方法。
• 2(3H)-Oxazolones from α-Hydroxy Amides and Keteneylidenetriphenylphosphorane via a Phoshorus Ylide Cascade
  作者：Jonas Löffler、Rainer Schobert

  DOI：10.1002/jlac.199719970132

  日期：1997.1

  activity”. Evidence for the proposed mechanism is provided by trapping the intermediate ylide species with suitable carbonyl compounds. This technique may also be used to exclusively prepare the 2,4-oxazolidinediones 13 in good yields.

  在二甲苯中加热后，α-羟基酰胺3与累积的磷内鎓盐1反应，以40-80％的收率得到取代的2（3 H）-恶唑酮8。经由加料/环化/反应的进行间分子Wittig烯化序列，这意味着三种不同类型的增加“叶立德活性”的磷叶立德。通过用合适的羰基化合物捕获中间叶立德物质，为提出的机理提供了证据。该技术还可用于以良好的产率专门制备2，4-恶唑烷二酮13。