N-allyloxycarbonyl-N-(2-methoxy-2-oxoethyl)-D,L-leucyl methyl thioimidate | 936368-06-8

• 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: N-allyloxycarbonyl-N-(2-methoxy-2-oxoethyl)-D,L-leucyl methyl thioimidate
• 英文别名: Methyl 2-[(1-imino-4-methyl-1-methylsulfanylpentan-2-yl)-prop-2-enoxycarbonylamino]acetate
• CAS: 936368-06-8
• 化学式: C₁₄H₂₄N₂O₄S
• 分子量: 316.422
• InChiKey: KKDSETGJBLTBOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-allyloxycarbonyl-N-(2-methoxy-2-oxoethyl)-D,L-leucyl methyl thioimidate 在 N,N-二异丙基乙胺 作用下， 生成 allyl N-(2-methoxy-2-oxoethyl)-N-(1-cyano-3-methylbutyl) carbamate
  参考文献：
  名称：

  Synthesis of Amino Acid-Derived Cyclic Acyl Amidines for Use in β-Strand Peptidomimetics

  摘要：

  The acyl amidine represented by the 4,5-dihydro-2(3H)-pyrazinone ring system 2 is isosteric to the vinylogous amide of the 1,2-dihydro-3(6H)-pyridinone 1, but its assembly from separate amine and amide components enables ready incorporation of an amino acid side chain with correct regio- and stereochemistry. beta-Strand peptidomimetics incorporating amino acid analogues based on 2 have recently been shown to be potent, protease-resistant ligands to a PDZ protein-interaction domain. Two routes to the protected dipeptide analogue 3 are described.

  DOI：

  10.1021/jo062664i
• 作为产物：
  描述：

  L-亮氨酰胺盐酸盐 在 劳森试剂 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 41.5h， 生成 N-allyloxycarbonyl-N-(2-methoxy-2-oxoethyl)-D,L-leucyl methyl thioimidate
  参考文献：
  名称：

  Synthesis of Amino Acid-Derived Cyclic Acyl Amidines for Use in β-Strand Peptidomimetics

  摘要：

  The acyl amidine represented by the 4,5-dihydro-2(3H)-pyrazinone ring system 2 is isosteric to the vinylogous amide of the 1,2-dihydro-3(6H)-pyridinone 1, but its assembly from separate amine and amide components enables ready incorporation of an amino acid side chain with correct regio- and stereochemistry. beta-Strand peptidomimetics incorporating amino acid analogues based on 2 have recently been shown to be potent, protease-resistant ligands to a PDZ protein-interaction domain. Two routes to the protected dipeptide analogue 3 are described.

  DOI：

  10.1021/jo062664i

文献信息

• Synthesis of Amino Acid-Derived Cyclic Acyl Amidines for Use in β-Strand Peptidomimetics
  作者：Ming C. Hammond、Paul A. Bartlett

  DOI：10.1021/jo062664i

  日期：2007.4.1

  The acyl amidine represented by the 4,5-dihydro-2(3H)-pyrazinone ring system 2 is isosteric to the vinylogous amide of the 1,2-dihydro-3(6H)-pyridinone 1, but its assembly from separate amine and amide components enables ready incorporation of an amino acid side chain with correct regio- and stereochemistry. beta-Strand peptidomimetics incorporating amino acid analogues based on 2 have recently been shown to be potent, protease-resistant ligands to a PDZ protein-interaction domain. Two routes to the protected dipeptide analogue 3 are described.