(+)-(R)-N²-(tert-butoxycarbonyl)-N¹-(2-methylphenyl)alaninamide | 936627-91-7

• 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-methylphenyl)alaninamide
• 英文别名: N-tert-butoxycarbonyl-alaninyl-o-toluidine；tert-butyl N-[(2R)-1-(2-methylanilino)-1-oxopropan-2-yl]carbamate
• CAS: 936627-91-7
• 化学式: C₁₅H₂₂N₂O₃
• 分子量: 278.351
• InChiKey: YCKHLBOPDKTVFH-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-(R)-N²-(tert-butoxycarbonyl)-N¹-(2-methylphenyl)alaninamide 在 盐酸 作用下， 以 乙醚 为溶剂， 反应 0.25h， 以47%的产率得到(2R)-2-amino-N-(2-methylphenyl)propanamide;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-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 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-methylphenyl)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

• Synthesis of organometallic amines and their coupling to the C-terminus of amino acids and peptides
  作者：Alexandra Hess、Oliver Brosch、Thomas Weyhermüller、Nils Metzler-Nolte

  DOI：10.1016/s0022-328x(99)00304-6

  日期：1999.10

  solution. For the glycine derivative 4a the activation energy was determined to be 70.3 kJ mol−1 by 1H-NMR spectroscopy. All new compounds were completely characterised spectroscopically including 15N-NMR by indirect detection 2D 1H-15N-NMR. The potential difference of ca. +50 mV between ferrocene derivatives 2 and the ferrocenyl amino acids 4 in cyclic voltammetry was used to monitor the peptide coupling

  这项工作描述了使用有机金属胺标记氨基酸和肽的C端。N-取代的二茂铁-甲胺2可以容易地制备并且以良好的产率偶联至多种氨基酸。新的二茂铁氨基酸衍生物4在溶液中以两种构象存在，它们在叔酰胺键的取向上不同并且在溶液中缓慢地相互转化。对于甘氨酸衍生物4a，通过1 H-NMR光谱确定活化能为70.3kJ mol -1。通过间接检测2D 1对所有新化合物进行光谱鉴定，包括15 N-NMRH - 15 N-NMR。约的电位差。在循环伏安法中，二茂铁衍生物2和二茂铁氨基酸4之间的+ 50mV被用于原位监测肽偶联反应。还描述了尝试合成苯铬三羰基和η-环戊二烯基二羰基钼的有机金属胺衍生物的尝试。合物CPMo（CO）的固态结构2 C 2 ħ 4 N（CO）2 C ^ 6 ħ 4 14和CPFeC 5 ħ 4 CH 2 NHCH 2 - p -CH 3C 6 ħ 4 2A（CP：η环戊二烯基），通过单晶X射线衍射来确定。