(S)-5-ethenyl-1-butenyl-2-pyrrolidinone | 139694-78-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S)-5-ethenyl-1-butenyl-2-pyrrolidinone
• 英文别名: (5S)-1-but-1-enyl-5-ethenylpyrrolidin-2-one
• CAS: 139694-78-3
• 化学式: C₁₀H₁₅NO
• 分子量: 165.235
• InChiKey: FTXYEDNDPNONKS-SECBINFHSA-N

物化性质

• 沸点：
  272.1±20.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-5-ethenyl-1-butenyl-2-pyrrolidinone 在 盐酸 作用下， 反应 5.0h， 以63%的产率得到(s)-4-氨基-5-己酸
  参考文献：
  名称：

  Asymmetric synthesis of (S)-4-aminohex-5-enoic acid: a potent inhibitor of 4-aminobutyrate-2-oxoglutarate aminotransferase

  摘要：

  The potent inhibitor of 4-aminobutyrate-2-oxoglutarate aminotransferase (GABA-T), 4-aminohex-5-enoic acid (vinyl GABA), has been synthesized with excellent enantioselectivity in six steps from L-glutamic acid in an overall yield of 33%. This is the most efficient synthesis of this important compound and illustrates the use of a novel alkenyl protecting group for pyroglutamate. This allowed the preparation and manipulation of the key (S)-2-oxopyrrolidine-5-carboxaldehyde intermediate.

  DOI：

  10.1021/jo00049a023
• 作为产物：
  描述：

  L-焦谷氨酸乙酯 在 吡啶 、 sodium tetrahydroborate 、 potassium tert-butylate 、 phosphorus pentoxide 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 乙醇 、 二甲基亚砜 、 甲苯 、 苯 为溶剂， 反应 58.17h， 生成 (S)-5-ethenyl-1-butenyl-2-pyrrolidinone
  参考文献：
  名称：

  Asymmetric synthesis of (S)-4-aminohex-5-enoic acid: a potent inhibitor of 4-aminobutyrate-2-oxoglutarate aminotransferase

  摘要：

  The potent inhibitor of 4-aminobutyrate-2-oxoglutarate aminotransferase (GABA-T), 4-aminohex-5-enoic acid (vinyl GABA), has been synthesized with excellent enantioselectivity in six steps from L-glutamic acid in an overall yield of 33%. This is the most efficient synthesis of this important compound and illustrates the use of a novel alkenyl protecting group for pyroglutamate. This allowed the preparation and manipulation of the key (S)-2-oxopyrrolidine-5-carboxaldehyde intermediate.

  DOI：

  10.1021/jo00049a023

文献信息

• Asymmetric synthesis of (S)-4-aminohex-5-enoic acid: a potent inhibitor of 4-aminobutyrate-2-oxoglutarate aminotransferase
  作者：Tae Woo Kwon、Paul F. Keusenkothen、Michael B. Smith

  DOI：10.1021/jo00049a023

  日期：1992.11

  The potent inhibitor of 4-aminobutyrate-2-oxoglutarate aminotransferase (GABA-T), 4-aminohex-5-enoic acid (vinyl GABA), has been synthesized with excellent enantioselectivity in six steps from L-glutamic acid in an overall yield of 33%. This is the most efficient synthesis of this important compound and illustrates the use of a novel alkenyl protecting group for pyroglutamate. This allowed the preparation and manipulation of the key (S)-2-oxopyrrolidine-5-carboxaldehyde intermediate.