methyl (2RS,3SR)-3-amino-2-ethylbutanoate

• 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: methyl (2RS,3SR)-3-amino-2-ethylbutanoate
• 英文别名: methyl (2R,3S)-3-amino-2-ethylbutanoate
• 化学式: C₇H₁₅NO₂
• 分子量: 145.202
• InChiKey: DBQGCFVOOMYRCC-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2RS,3SR)-3-amino-2-ethylbutanoate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 (3R,4S)-3-ethyl-4-methylazetidin-2-one
  参考文献：
  名称：

  A New Method for the Synthesis of β-Amino Acid Derivatives and β-Lactams. Reaction of N-Alkoxycarbonyl-1-methoxyamines with Esters

  摘要：

  The reaction of N-alkoxycarbonyl-1-methoxyamines with esters is an alternative to the reaction of imines with esters for the synthesis of beta-amino acid derivatives. In this reaction, N-alkoxycarbony-1-methoxyamines corresponding to unstable imines can also be employed. Although anti adducts were obtained preferentially in the absence of Ti complexes, the diastereoselectivity of this reaction was reversed by the addition of Ti(OPr-i)(4). The obtained adducts were transformed to the corresponding beta-lactams.

  DOI：

  10.1021/jo990821q
• 作为产物：
  描述：

  (2S,3R)-2-Ethyl-3-methoxycarbonylamino-butyric acid methyl ester 在 氢溴酸 、 溶剂黄146 作用下， 生成 methyl (2RS,3SR)-3-amino-2-ethylbutanoate
  参考文献：
  名称：

  A New Method for the Synthesis of β-Amino Acid Derivatives and β-Lactams. Reaction of N-Alkoxycarbonyl-1-methoxyamines with Esters

  摘要：

  The reaction of N-alkoxycarbonyl-1-methoxyamines with esters is an alternative to the reaction of imines with esters for the synthesis of beta-amino acid derivatives. In this reaction, N-alkoxycarbony-1-methoxyamines corresponding to unstable imines can also be employed. Although anti adducts were obtained preferentially in the absence of Ti complexes, the diastereoselectivity of this reaction was reversed by the addition of Ti(OPr-i)(4). The obtained adducts were transformed to the corresponding beta-lactams.

  DOI：

  10.1021/jo990821q

文献信息

• Expanding dynamic kinetic protocols: transaminase-catalyzed synthesis of α-substituted β-amino ester derivatives
  作者：Aníbal Cuetos、Iván Lavandera、Vicente Gotor

  DOI：10.1039/c3cc46760k

  日期：——

  Several α-alkylated β-amino esters have been obtained via DKR processes employing a kit of transaminases and isopropylamine as an amino donor in aqueous medium under mild conditions. Thus, while acyclic α-alkyl-β-keto esters afforded excellent conversions and enantioselectivities, although usually low diastereoselectivities, using more constrained cyclic β-keto esters high to excellent inductions were obtained.

  通过使用一套转氨酶和异丙胺作为氨基供体，在温和条件下的水相介质中，已获得几种α-烷基化β-氨基酯。这些非环状α-烷基-β-酮酯表现出优异的转化率和对映选择性，尽管通常具有较低的非对映选择性。然而，使用更受限的环状β-酮酯时，获得了高至优异的诱导效果。