4-(N-(methoxycarbonyl)formamido)butanoic acid | 1092074-45-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-(N-(methoxycarbonyl)formamido)butanoic acid
• 英文别名: 4-[Formyl(methoxycarbonyl)amino]butanoic acid；4-[formyl(methoxycarbonyl)amino]butanoic acid
• CAS: 1092074-45-7
• 化学式: C₇H₁₁NO₅
• 分子量: 189.168
• InChiKey: MCRYQLKDTAKWKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  哌啶-1-羧酸甲酯 在 硝酸 、 三氟乙酸 作用下， 反应 3.0h， 以81%的产率得到4-(N-(methoxycarbonyl)formamido)butanoic acid
  参考文献：
  名称：

  Oxidative C-C Bond Cleavage of N-Protected Cyclic Amines by HNO3-TFA System

  摘要：

  Oxidative C-C bond cleavage of N-protected cyclic amines was achieved by using 70% HNO3 in trifluoroacetic acid (TFA) to afford omega-amino acid derivatives in high yields. The C-C bond cleavage reaction smoothly proceeded under aerobic condition with a simple procedure. The use of 70% HNO3 as an oxidant source enabled to conduct the reaction at a higher substrate concentration than that of the previous condition using NaNO2 in TFA. In addition, some omega-amino acids were obtained with improved reaction efficiency under the present reaction conditions.

  DOI：

  10.3987/com-19-s(f)31

文献信息

• Oxidative C–C bond cleavage of N-alkoxycarbonylated cyclic amines by sodium nitrite in trifluoroacetic acid
  作者：Osamu Onomura、Atsushi Moriyama、Kazuhiro Fukae、Yutaka Yamamoto、Toshihide Maki、Yoshihiro Matsumura、Yosuke Demizu

  DOI：10.1016/j.tetlet.2008.09.067

  日期：2008.11

  Oxidative carbon-carbon bond cleavage of N-alkoxycarbonylated cyclic amines was accomplished by NaNO2, in TFA to afford omega-amino carboxylic acid in high yield. Optically active 3-hydroxypiperidine derivatives and 3-pipecolinate were converted to enantiomerically pure (R)-4-amino-3-hydroxybutanoic acid (GABOB) and (S)-2-pyrrolidone-4-carboxylate, respectively. (c) 2008 Elsevier Ltd. All rights reserved.
• Oxidative C-C Bond Cleavage of N-Protected Cyclic Amines by HNO3-TFA System
  作者：Osamu Onomura、Kosuke Yamamoto、Hiroyuki Toguchi、Toshihiro Harada、Masami Kuriyama

  DOI：10.3987/com-19-s(f)31

  日期：——

  Oxidative C-C bond cleavage of N-protected cyclic amines was achieved by using 70% HNO3 in trifluoroacetic acid (TFA) to afford omega-amino acid derivatives in high yields. The C-C bond cleavage reaction smoothly proceeded under aerobic condition with a simple procedure. The use of 70% HNO3 as an oxidant source enabled to conduct the reaction at a higher substrate concentration than that of the previous condition using NaNO2 in TFA. In addition, some omega-amino acids were obtained with improved reaction efficiency under the present reaction conditions.