N-<(1S,2S)-1-methoxycarbonyl-2-methylbutyl>-(5S)-5-amino-3-methoxy-5-phenyl-pent-2-enoic acid methyl ester | 139327-30-3

• 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-<(1S,2S)-1-methoxycarbonyl-2-methylbutyl>-(5S)-5-amino-3-methoxy-5-phenyl-pent-2-enoic acid methyl ester
• 英文别名: methyl (2S,3S)-2-[[(E,1S)-3,5-dimethoxy-5-oxo-1-phenylpent-3-enyl]amino]-3-methylpentanoate
• CAS: 139327-30-3
• 化学式: C₂₀H₂₉NO₅
• 分子量: 363.454
• InChiKey: BJTDUPSOKNOYFN-BHFNNLJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  L-异亮氨酸甲酯 在 二氯乙基铝 作用下， 以 乙醚 为溶剂， 反应 2.28h， 生成 N-<(1S,2S)-1-methoxycarbonyl-2-methylbutyl>-(5S)-5-amino-3-methoxy-5-phenyl-pent-2-enoic acid methyl ester
  参考文献：
  名称：

  Asymmetric aza Diels-Alder reactions of amino acid ester imines with Brassard's diene

  摘要：

  Imines 1 obtained from aromatic, aliphatic or functionalized aldehydes and valine tert-butyl ester undergo Lewis acid catalyzed hetero Diels-Alder reactions with Brassard's diene 2. The cycloadducts are formed in good to high yields and with diastereomer ratios of 92:8-97:3. For the removal of the chiral auxiliary group a new method was developed whose principle consists in the conversion of the amino acid alpha-C-atom into an acetalic center employing a Curtius rearrangement as the key step.

  DOI：

  10.1016/s0957-4166(00)80023-3

文献信息

• Asymmetric aza Diels-Alder reactions of amino acid ester imines with Brassard's diene
  作者：Herbert Waldmann、Matthias Braun、Martin Dräger

  DOI：10.1016/s0957-4166(00)80023-3

  日期：1991.1

  Imines 1 obtained from aromatic, aliphatic or functionalized aldehydes and valine tert-butyl ester undergo Lewis acid catalyzed hetero Diels-Alder reactions with Brassard's diene 2. The cycloadducts are formed in good to high yields and with diastereomer ratios of 92:8-97:3. For the removal of the chiral auxiliary group a new method was developed whose principle consists in the conversion of the amino acid alpha-C-atom into an acetalic center employing a Curtius rearrangement as the key step.