(+)-(R)-N2-(tert-butoxycarbonyl)-N1-(2,6-dimethylphenyl)alaninamide | 151416-30-7

• 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: (+)-(R)-N2-(tert-butoxycarbonyl)-N1-(2,6-dimethylphenyl)alaninamide
• 英文别名: (+)-(R)-N²-(tert-butoxycarbonyl)-N¹-(2,6-dimethylphenyl)alaninamide；tert-butyl (2R)-(1-((2,6-dimethylphenyl)amino)-1-oxopropan-2-yl)carbamate
• CAS: 151416-30-7
• 化学式: C₁₆H₂₄N₂O₃
• 分子量: 292.378
• InChiKey: ZZRLCIVRQJCXQB-GFCCVEGCSA-N

物化性质

• 沸点：
  440.0±33.0 °C(predicted)
• 密度：
  1.095±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.43
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (+)-(R)-N2-(tert-butoxycarbonyl)-N1-(2,6-dimethylphenyl)alaninamide 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 0.25h， 生成 (-)-Tocainide hydrochloride
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Chiral α-Aminoanilides with Central Antinociceptive Activity

  摘要：

  Tocainide and related optically active chiral alpha-aminoanilides were synthesized and tested in vivo via the hot plate test to evaluate their central analgesic action. The aims of the study were to verify if a) the increase in lipophilicity, obtained by the introduction of an alkyl group on the steric center (3f-i), and the replacement of the C=O group with the C=S (10) group as well as the introduction of a methyl or ethyl group on the amidic nitrogen atom (8a-c) would produce an increase in central analgesic efficacy with respect to Tocainide; b) the 2,6-xylidide moiety is crucial for high analgesic activity (3b-e); c) the hydrogen atom bonded to the amidic nitrogen moiety is an essential pharmacophoric element for analgesic activity. Among all the synthesized compounds, 3f showed antinociceptive properties with a good enantioselective index.

  DOI：

  10.1021/jm061078e
• 作为产物：
  描述：

  2-(t-butoxycarbonyloxyimino)-2-phenylacetonitrile 在 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline 、 三乙胺 作用下， 以 1,4-二氧六环 、 氯仿 、 水 为溶剂， 反应 6.0h， 生成 (+)-(R)-N2-(tert-butoxycarbonyl)-N1-(2,6-dimethylphenyl)alaninamide
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Chiral α-Aminoanilides with Central Antinociceptive Activity

  摘要：

  Tocainide and related optically active chiral alpha-aminoanilides were synthesized and tested in vivo via the hot plate test to evaluate their central analgesic action. The aims of the study were to verify if a) the increase in lipophilicity, obtained by the introduction of an alkyl group on the steric center (3f-i), and the replacement of the C=O group with the C=S (10) group as well as the introduction of a methyl or ethyl group on the amidic nitrogen atom (8a-c) would produce an increase in central analgesic efficacy with respect to Tocainide; b) the 2,6-xylidide moiety is crucial for high analgesic activity (3b-e); c) the hydrogen atom bonded to the amidic nitrogen moiety is an essential pharmacophoric element for analgesic activity. Among all the synthesized compounds, 3f showed antinociceptive properties with a good enantioselective index.

  DOI：

  10.1021/jm061078e

文献信息

• Amine Activation:<i>N</i>-Arylamino Acid Amide Synthesis from Isothioureas and Amino Acids
  作者：Yan-Ping Zhu、Pieter Mampuys、Sergey Sergeyev、Steven Ballet、Bert U. W. Maes

  DOI：10.1002/adsc.201700134

  日期：2017.7.17

  functional group compatibility, with respect to side chain functionality of the amino acid (e. g. aliphatic and aromatic OH, (hetero)aromatic NH, amide NH, thioether), and the chiral amino acids do not undergo epimerization. The mechanism of the new amide synthesis has been studied.

  Ñ -arylamino酰胺已经通过基于新方法被合成ñ -芳基胺活化成异硫脲，随后用下铁催化氨基酸反应。可以使用三组分反应与市售试剂叔丁基异氰化物和S-苯基苯硫代磺酸盐轻松地制备活化的N-芳基胺。相对于氨基酸（例如脂族和芳族OH，（杂）芳族NH，酰胺NH，硫醚）的侧链官能度，该方案显示出广泛的官能团相容性，并且手性氨基酸不发生差向异构化。已经研究了新酰胺合成的机理。