N-苄基-2-羟基-2-甲基丙酰胺 | 100369-89-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-苄基-2-羟基-2-甲基丙酰胺
• 英文名称: N-benzyl-2-hydroxy-2-methylpropanamide
• 英文别名: N-phenetyl-2-hydroxyisobutylamide；α-hydroxy-isobutyric acid phenethylamide；α-Hydroxy-isobuttersaeure-phenaethylamid；2-hydroxy-2-methyl-N-(2-phenylethyl)propanamide
• CAS: 100369-89-9
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: FEWDJZRKPIWLGV-UHFFFAOYSA-N

物化性质

• 沸点：
  405.3±38.0 °C(Predicted)
• 密度：
  1.080±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 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-苄基-2-羟基-2-甲基丙酰胺 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 5,5-Dimethyl-2,2-dioxo-3-(2-phenylethyl)oxathiazolidin-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：

  2-甲基-2-羟基丙酸 、 2-苯乙胺 在 甲基硼酸 、 水 作用下， 以 甲苯 为溶剂， 反应 17.0h， 以86%的产率得到N-苄基-2-羟基-2-甲基丙酰胺
  参考文献：
  名称：

  伯烷基硼酸作为α-羟基羧酸脱水酰胺缩合的高活性催化剂

  摘要：

  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。

  DOI：

  10.1021/ol401537f

文献信息

• EP2816026
  申请人：——

  公开号：——

  公开（公告）日：——
• α-Hydroxy Amides and Related Compounds
  作者：Seymour L. Shapiro、Ira M. Rose、Louis Freedman

  DOI：10.1021/ja01532a052

  日期：1959.12
• 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。
• Synthesis and anticonvulsant activity of bioisosteres of trimethadione, N-derivative-1,2,3-oxathiazolidine-4-one-2,2-dioxides from α-hydroxyamides
  作者：Valentina Pastore、Laureano Sabatier、Andrea Enrique、Mariel Marder、Luis E. Bruno-Blanch

  DOI：10.1016/j.bmc.2012.12.033

  日期：2013.2

  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.