methyl (E,2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-oxohex-4-enoate | 116613-74-2

• 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 (E,2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-oxohex-4-enoate
• CAS: 116613-74-2
• 化学式: C₁₂H₁₉NO₅
• 分子量: 257.287
• InChiKey: YGKPDOWGFACMCK-CYNONHLPSA-N

物化性质

• 熔点：
  60-62.5 °C
• 沸点：
  388.4±42.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (E,2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-oxohex-4-enoate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以87%的产率得到(E)-(S)-2-tert-Butoxycarbonylamino-6-hydroxy-hex-4-enoic acid methyl ester
  参考文献：
  名称：

  A facile synthesis of (S)-gizzerosine, a potent agonist of the histamine H2-receptor

  摘要：

  A simple and direct approach for the synthesis of (S)-gizzerosine, an amino acid responsible for the disease, black vomit, and a potent histamine H-2-receptor, has been developed in 10 steps and in 31% overall yield from L-aspartic acid. The key steps involved a two-carbon homologation of an L-aspartic acid semi-aldehyde and direct alkylation of unprotected histamine with a 6-hydroxynorleucine derivative. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.09.165
• 作为产物：
  描述：

  甲酰甲撑基三苯基磷 、 methyl (S)-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate 以 四氢呋喃 为溶剂， 反应 48.0h， 以92%的产率得到methyl (E,2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-oxohex-4-enoate
  参考文献：
  名称：

  A facile synthesis of (S)-gizzerosine, a potent agonist of the histamine H2-receptor

  摘要：

  A simple and direct approach for the synthesis of (S)-gizzerosine, an amino acid responsible for the disease, black vomit, and a potent histamine H-2-receptor, has been developed in 10 steps and in 31% overall yield from L-aspartic acid. The key steps involved a two-carbon homologation of an L-aspartic acid semi-aldehyde and direct alkylation of unprotected histamine with a 6-hydroxynorleucine derivative. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.09.165

文献信息

• A facile synthesis of (S)-gizzerosine, a potent agonist of the histamine H2-receptor
  作者：Kate N. Fanning、Andrew Sutherland

  DOI：10.1016/j.tetlet.2007.09.165

  日期：2007.11

  A simple and direct approach for the synthesis of (S)-gizzerosine, an amino acid responsible for the disease, black vomit, and a potent histamine H-2-receptor, has been developed in 10 steps and in 31% overall yield from L-aspartic acid. The key steps involved a two-carbon homologation of an L-aspartic acid semi-aldehyde and direct alkylation of unprotected histamine with a 6-hydroxynorleucine derivative. (c) 2007 Elsevier Ltd. All rights reserved.