2-Amino-3-methyl-3-butencarbonsaeure-hydrochlorid

• 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: 2-Amino-3-methyl-3-butencarbonsaeure-hydrochlorid
• 英文别名: (+/-)-isodehydrovaline hydrochloride；(1-carboxy-2-methylprop-2-enyl)azanium;chloride
• 化学式: C₅H₉NO₂*ClH
• 分子量: 151.593
• InChiKey: CAZJBBFHMUQMGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  63.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Amino-3-methyl-3-butencarbonsaeure-hydrochlorid 在 methyloxirane 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以97%的产率得到2-Amino-3-methyl-3-butencarbonsaeure
  参考文献：
  名称：

  �ber einen neuartigen synthetischen Zugang zu ?,?-unges�ttigten ?-Aminocarbons�uren

  摘要：

  A New Synthetic Route to β,α‐Unsaturated α‐Amino AcidsA versatile new synthetic pathway for the preparation of βγ‐unsaturated α‐amino acids (1) is presented. Cu(I)‐catalyzed addition of ethyl isocyanoacetate (2) to α‐chloro carbonyl compounds (3) gives 5‐chloroalkyl‐2‐oxazolin‐4‐carboxylates (4) in high yields. A reductive elimination on 4 by means of zinc yields the N‐formyl derivatives of βγ‐unsaturated α‐amino carboxylates (5), which on acid hydrolysis lead to the free amino acids 1. The five different βγ‐dehydro‐α‐amono acids 1b‐1f have been prepared by this method.

  DOI：

  10.1002/hlca.19810640734
• 作为产物：
  描述：

  ethyl 2-nitro-3-methylbut-3-enoate 在 盐酸 、 tin 作用下， 以 水 为溶剂， 以0.2 g的产率得到2-Amino-3-methyl-3-butencarbonsaeure-hydrochlorid
  参考文献：
  名称：

  Exploration of the Molecular Origin of the Azinomycin Epoxide: Timing of the Biosynthesis Revealed

  摘要：

  Streptomyces sahachiroi whole cell feeding experiments, utilizing putative precursors labeled with stable isotopes, established that the epoxide unit of the DNA cross-linked agents, azinomycin A and B, proceeds via a valine-dependent pathway and that hydroxylation and dehydration precedes formation of the terminal epoxide. Sodium 3-methyl-2-oxobutenoate, formed through a transimination reaction, was shown to be the penultimate precursor incorporated into the azinomycin epoxide.

  DOI：

  10.1021/ol8018852

文献信息

• HEINZER, F.;BELLUS, D., HELV. CHIM. ACTA, 1981, 64, N 7, 2279-2297
  作者：HEINZER, F.、BELLUS, D.

  DOI：——

  日期：——
• �ber einen neuartigen synthetischen Zugang zu ?,?-unges�ttigten ?-Aminocarbons�uren
  作者：Franz Heinzer、Daniel Bellu?

  DOI：10.1002/hlca.19810640734

  日期：1981.11.4

  A New Synthetic Route to β,α‐Unsaturated α‐Amino AcidsA versatile new synthetic pathway for the preparation of βγ‐unsaturated α‐amino acids (1) is presented. Cu(I)‐catalyzed addition of ethyl isocyanoacetate (2) to α‐chloro carbonyl compounds (3) gives 5‐chloroalkyl‐2‐oxazolin‐4‐carboxylates (4) in high yields. A reductive elimination on 4 by means of zinc yields the N‐formyl derivatives of βγ‐unsaturated α‐amino carboxylates (5), which on acid hydrolysis lead to the free amino acids 1. The five different βγ‐dehydro‐α‐amono acids 1b‐1f have been prepared by this method.
• Exploration of the Molecular Origin of the Azinomycin Epoxide: Timing of the Biosynthesis Revealed
  作者：Vasudha Sharma、Gilbert T. Kelly、Coran M. H. Watanabe

  DOI：10.1021/ol8018852

  日期：2008.11.6

  Streptomyces sahachiroi whole cell feeding experiments, utilizing putative precursors labeled with stable isotopes, established that the epoxide unit of the DNA cross-linked agents, azinomycin A and B, proceeds via a valine-dependent pathway and that hydroxylation and dehydration precedes formation of the terminal epoxide. Sodium 3-methyl-2-oxobutenoate, formed through a transimination reaction, was shown to be the penultimate precursor incorporated into the azinomycin epoxide.