Alloc-(cyclo-p-ClC6H4CH)-Asn-H | 250264-85-8

• 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: Alloc-(cyclo-p-ClC6H4CH)-Asn-H
• 英文别名: (2S,4S)-2-(4-chlorophenyl)-6-oxo-3-prop-2-enoxycarbonyl-1,3-diazinane-4-carboxylic acid
• CAS: 250264-85-8
• 化学式: C₁₅H₁₅ClN₂O₅
• 分子量: 338.748
• InChiKey: ITDGKOCVVZYHSR-AAEUAGOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Alloc-(cyclo-p-ClC6H4CH)-Asn-H 在 potassium tert-butylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 Alloc-(cyclo-p-ClC6H4CH)-MeAsn-OMe
  参考文献：
  名称：

  Enantiomerically Pure Tetrahydropyrimidinones in Asymmetric Synthesis:  Preparation of a Protected α-Methylasparagine Derivative and Corresponding Dipeptides

  摘要：

  Methyl ester 5a, available in enantiomerically pure form from the amino acid asparagine via a one-pot cyclization/protection sequence, followed by esterification, can be effectively deprotonated with LDA/DMPU/LiCl. Treatment with Mel affords the corresponding alkylated adduct in enantiomerically pure form, from which alpha-methylaspartic acid is obtained. Variation of the amine protection group allows for the isolation of a protected carboxylic acid/free amine derivative of alpha-methylasparagine. The utility of H-MeAsn-OMe is demonstrated in the formation of dipeptides.

  DOI：

  10.1021/jo9909296
• 作为产物：
  描述：

  L-天冬酰胺 、 4-氯苯甲醛 、 氯甲酸烯丙酯 在 氢氧化钾 、 碳酸氢钠 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 48.0h， 生成 Alloc-(cyclo-p-ClC6H4CH)-Asn-H
  参考文献：
  名称：

  Enantiomerically Pure Tetrahydropyrimidinones in Asymmetric Synthesis:  Preparation of a Protected α-Methylasparagine Derivative and Corresponding Dipeptides

  摘要：

  Methyl ester 5a, available in enantiomerically pure form from the amino acid asparagine via a one-pot cyclization/protection sequence, followed by esterification, can be effectively deprotonated with LDA/DMPU/LiCl. Treatment with Mel affords the corresponding alkylated adduct in enantiomerically pure form, from which alpha-methylaspartic acid is obtained. Variation of the amine protection group allows for the isolation of a protected carboxylic acid/free amine derivative of alpha-methylasparagine. The utility of H-MeAsn-OMe is demonstrated in the formation of dipeptides.

  DOI：

  10.1021/jo9909296