甘氨酸二甲苯胺盐酸盐 | 35891-83-9

• 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
• 中文名称: 甘氨酸二甲苯胺盐酸盐
• 中文别名: 盐酸甘氨二甲酰胺
• 英文名称: glycylxylidide hydrochloride
• 英文别名: 2-amino-N-[(2,6-dimethyl)phenyl]acetamide hydrochloride；N¹-(2,6-dimethylphenyl)-2-aminoacetamide hydrochloride；N'-2,6-dimethylphenyl glycinamide hydrochloride；2-amino-N-(2,6-dimethylphenyl)acetamide hydrochloride；2-amino-N-(2,6-dimethylphenyl)acetamide;hydrochloride
• CAS: 35891-83-9
• 化学式: C₁₀H₁₄N₂O*ClH
• mdl: MFCD07287371
• 分子量: 214.695
• InChiKey: HPVGPNNVMZBKIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.31
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.1
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二苯甲酮亚胺 、 甘氨酸二甲苯胺盐酸盐 以82%的产率得到N¹-(2,6-dimethylphenyl)-N²-(diphenylmethylene)glycinamide
  参考文献：
  名称：

  Phase transfer catalyzed asymmetric alkylations of imine glycinamides

  摘要：

  Herein we report the use of achiral imine glycinamides as substrates for asymmetric alkylations using chiral phase-transfer catalysts for the first time. Initially tried for obtaining a key intermediate for the synthesis of levobupivacaine, we expanded the study to other N-mono and N,N-disubstituted imine glycinamides. A possible explanation for the lower enantioselectivity observed in the ease of alkylation of N-monosubstituted as compared to N,N-disubstituted glycinamides is also provided. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00441-5
• 作为产物：
  描述：

  tert-butyl (2-((2,6-dimethylphenyl)amino)-2-oxoethyl)carbamate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 以94.8 %的产率得到甘氨酸二甲苯胺盐酸盐
  参考文献：
  名称：

  酸合作过渡金属催化氧原子转移：钌催化 C-H 氧化

  摘要：

  开发控制金属（氧）反应性的方法的前景对合成化学和生物无机化学都有吸引力。在这项研究中，我们观察到羧酸通过与氧代配体形成氢键来增强C-H氧化反应活性，从而增加氧代中间体的碱性和亲电性。此外，我们发现 H-二羧酸配体，如草酸、丙二酸和马来酸，可显着提高未活化 C(sp3)-H 氧化中的催化剂周转频率（高达 760/h）。此外，还发现马来酸的添加可以激活 Fe 和 Mn(pdp) 催化的 C-H 氧化。值得注意的是，Ru(bpga)(H-马来酸酯)2 3-催化的C-H官能化表现出广泛的官能团耐受性，包括溴、羟基、苯甲酸酯、硝基、硝基、磺酸酯、酰亚胺、磺酰胺和氨基甲酸酯，产率高达98 % 以位点和化学选择性方式，负载量仅为 0.1-2.0 mmol%。

  DOI：

  10.1002/adsc.202301453

文献信息

• Synthesis and structure–activity relationships of potential anticonvulsants based on 2-piperidinecarboxylic acid and related pharmacophores
  作者：Bin Ho、A Michael Crider、James P Stables

  DOI：10.1016/s0223-5234(00)01206-x

  日期：2001.3

  Using N-(2,6-dimethyl)phenyl-2-piperidinecarboxamide (1) and N-(alpha -methylbenzyl)-2-piperidinecarboxamide (2) as structural leads, a variety of analogues were synthesised and evaluated for anticonvulsant activity in the MES test in mice. In the N-benzyl series, introduction of 3-Cl, 4-Cl, 3,4-Cl-2, or 3-CF3 groups on the aromatic ring led to an increase in MES activity. Replacement of the alpha -methyl group by either i-Pr or benzyl groups enhanced MES activity with no increase in neurotoxicity. Substitution on the piperidine ring nitrogen led to a decrease in MES activity and neurotoxicity, while reduction of the amide carbonyl led to a complete loss of activity. Movement of the carboxamide group to either the 3- or 4-positions of the piperidine ring decreased MES activity and neurotoxicity. Incorporation of the piperidine ring into a tetrahydroisoquinoline or diazahydrinone nucleus led to increased neurotoxicity. In the N-(2,6-dimethyl)phenyl series, opening of the piperidine ring between the 1- and 6-positions gave the active norleucine derivative 75 (ED50 = 5.8 mg kg(-1), TD50 = 36.4 mg kg(-1), PI = 6.3). Replacement of the piperidine ring of I by cycloalkane (cyclohexane, cyclopentane, and cyclobutane) resulted in compounds with decreased MES activity and neurotoxicity, whereas replacement of the piperidine ring by a 4-pyridyl group led to a retention of MES activity with a comparable PI. Simplification of the 2-piperidinecarboxamide nucleus of 1 into a glycinecarboxamide nucleus led to about a six-fold decrease in MES activity. The 2,6-dimethylanilides were the most potent compounds in the MES test in each group of compounds evaluated, and compounds 50 and 75 should be useful leads in the development of agents for the treatment of tonic-clonic and partial seizures in man. (C) 2001 Editions scientifiques et medicales Elsevier SAS.
• BYRNES E. W.; MCMASTER P. D.; SMITH E. R.; BLAIR M. R.; BOYES R. N.; DUCE+, J. MED. CHEM., 1979, 22, NO 10, 1171-1176
  作者：BYRNES E. W.、 MCMASTER P. D.、 SMITH E. R.、 BLAIR M. R.、 BOYES R. N.、 DUCE+

  DOI：——

  日期：——