N2-Boc-β-(p-tolyl)-D-alaninamide | 1246351-10-9

• 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
• 英文名称: N2-Boc-β-(p-tolyl)-D-alaninamide
• 英文别名: tert-butyl N-[(2R)-1-amino-3-(4-methylphenyl)-1-oxopropan-2-yl]carbamate
• CAS: 1246351-10-9
• 化学式: C₁₅H₂₂N₂O₃
• 分子量: 278.351
• InChiKey: MBKHYVCTIRLJGN-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N2-Boc-β-(p-tolyl)-D-alaninamide 在 盐酸 、 水 作用下， 反应 3.0h， 以95%的产率得到β-(p-tolyl)-D-alanine hydrochloride
  参考文献：
  名称：

  Enantiopure trans-3-Arylaziridine-2-carboxamides: Preparation by Bacterial Hydrolysis and Ring-Openings toward Enantiopure, Unnatural d-α-Amino Acids

  摘要：

  Several racemic trans-3-arylaziridine-2-carboxamides were prepared and then resolved by Rhodococcus rhodochrous IFO 15564-catalyzed hydrolysis. The resulting enantiopure (2R,3S)-3-arylaziridine-2-carboxamides are adequate substrates to undergo fully stereoselective nucleophilic ring-openings at the C-3 ring position to finally yield enantiopure, unnatural D-alpha-aminocarboxylic acids. Experimental evidence is provided that suggests the fate of the (2S,3R)-3-arylaziridine-2-carboxylic acids concomitantly formed during the resolution processes. In this context, the similar bacterial resolution of racemic 1-arylaziridine-2-carboxamides and -carbonitriles, previously investigated by our research group, has been partially re-examined.

  DOI：

  10.1021/jo101377j
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 (R)-2-amino-3-(4-methylphenyl)propanamide 以 甲醇 为溶剂， 以83%的产率得到N2-Boc-β-(p-tolyl)-D-alaninamide
  参考文献：
  名称：

  Enantiopure trans-3-Arylaziridine-2-carboxamides: Preparation by Bacterial Hydrolysis and Ring-Openings toward Enantiopure, Unnatural d-α-Amino Acids

  摘要：

  Several racemic trans-3-arylaziridine-2-carboxamides were prepared and then resolved by Rhodococcus rhodochrous IFO 15564-catalyzed hydrolysis. The resulting enantiopure (2R,3S)-3-arylaziridine-2-carboxamides are adequate substrates to undergo fully stereoselective nucleophilic ring-openings at the C-3 ring position to finally yield enantiopure, unnatural D-alpha-aminocarboxylic acids. Experimental evidence is provided that suggests the fate of the (2S,3R)-3-arylaziridine-2-carboxylic acids concomitantly formed during the resolution processes. In this context, the similar bacterial resolution of racemic 1-arylaziridine-2-carboxamides and -carbonitriles, previously investigated by our research group, has been partially re-examined.

  DOI：

  10.1021/jo101377j

文献信息

• Enantiopure <i>trans</i>-3-Arylaziridine-2-carboxamides: Preparation by Bacterial Hydrolysis and Ring-Openings toward Enantiopure, Unnatural <scp>d</scp>-α-Amino Acids
  作者：Roberto Morán-Ramallal、Ramón Liz、Vicente Gotor

  DOI：10.1021/jo101377j

  日期：2010.10.1

  Several racemic trans-3-arylaziridine-2-carboxamides were prepared and then resolved by Rhodococcus rhodochrous IFO 15564-catalyzed hydrolysis. The resulting enantiopure (2R,3S)-3-arylaziridine-2-carboxamides are adequate substrates to undergo fully stereoselective nucleophilic ring-openings at the C-3 ring position to finally yield enantiopure, unnatural D-alpha-aminocarboxylic acids. Experimental evidence is provided that suggests the fate of the (2S,3R)-3-arylaziridine-2-carboxylic acids concomitantly formed during the resolution processes. In this context, the similar bacterial resolution of racemic 1-arylaziridine-2-carboxamides and -carbonitriles, previously investigated by our research group, has been partially re-examined.