ethyl 2-amino-3-methoxycarbonyl-4-oxo-2-pentanoate | 127107-00-0

• 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: ethyl 2-amino-3-methoxycarbonyl-4-oxo-2-pentanoate
• 英文别名: ethyl 2-amino-3-methoxycarbonyl-4-oxo-2-pentenoate；1-O-ethyl 4-O-methyl (E)-3-acetyl-2-aminobut-2-enedioate
• CAS: 127107-00-0
• 化学式: C₉H₁₃NO₅
• 分子量: 215.206
• InChiKey: FDYCLFYXNSTKHZ-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.48
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  95.69
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-amino-3-methoxycarbonyl-4-oxo-2-pentanoate 在 Ni Raney W-2 咪唑 、 sodium tetrahydroborate 、 氢气 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.17h， 生成 (2S,3S)-2-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(trimethylsilanyl-amino)-succinic acid 4-ethyl ester 1-methyl ester
  参考文献：
  名称：

  A new simple route for the synthesis of (±)-2-azetidinones starting from β-enaminoketoesters

  摘要：

  beta -Enaminoketoesters 1, obtained through metal-catalysed reaction of methyl acetoacetate with alkyl cyanoformates have been conveniently transformed into beta -aminoesters 4, 5 by reduction of both the carbonyl group and the carbon-carbon double bond of the enaminoester moiety. These intermediates could be easily converted to (+/-)-2-azetidinones 6, 7 structurally related to thienamycin in good yield and high diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)01036-5
• 作为产物：
  描述：

  乙酰乙酸甲酯 、 氰基甲酸乙酯 在 乙酰丙酮锌 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以95%的产率得到ethyl 2-amino-3-methoxycarbonyl-4-oxo-2-pentanoate
  参考文献：
  名称：

  A new simple route for the synthesis of (±)-2-azetidinones starting from β-Enaminoketoesters

  摘要：

  beta-Enaminoketoesters, obtained by metal-catalyzed reaction between alkyl acetoacetates and alkyl cyanoformates, are useful starting materials for rapid access to beta-acetyl-dehydroaspartic acrid derivatives which could be transformed into (+/-)-2-azetidinones bearing a 1-hydroxy-ethyl substituent through suitable reductive processes. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01421-5

文献信息

• A new synthetic entry to 3-carboxamido-4-carboxylic acid derivatives of isoxazole and pyrazole
  作者：Chiara B. Vicentini、Manuela Mazzanti、Carlo F. Morelli、Maurizio Manfrini

  DOI：10.1002/jhet.5570370129

  日期：2000.1

  2-amino-3-methoxycarbonyl-4-oxo-2-pentenoate (3) reacts with hydroxylamine or hydrazines to give isoxazole and pyrazole ortho-dicarboxylic acid esters 4 and 5, respectively. Partial hydrolysis of diesters 4 and 5 afforded the corresponding dicarboxylic acid monoesters 6 and 7. Amidation of the intermediate acid chlorides 8,9 followed by hydrolysis of 4-methylesters 10, 11 gave the title compounds 1 and

  2-氨基-3-甲氧基羰基-4-氧代-2-戊烯酸乙酯（3）与羟胺或肼反应，分别得到异恶唑和吡唑原二羧酸酯4和5。二酯4和5的部分水解得到相应的二羧酸单酯6和7。中间体酰氯8，9的酰胺化，随后4-甲基酯10、11的水解分别得到标题化合物1和2。
• IIMORI TAKAMASA; NII YASUSHI; IZAWA TOSHIO; KOBAYASHI SUSUMU; OHNO MASAJI, TETRAHEDRON LETT., 1979, NO 27, 2525-2528
  作者：IIMORI TAKAMASA、 NII YASUSHI、 IZAWA TOSHIO、 KOBAYASHI SUSUMU、 OHNO MASAJI

  DOI：——

  日期：——
• VERONESE, AUGUSTO C.;GANDOLFI, VITTORIO;BASATO, MARINO;CORAIN, BENEDETTO
  作者：VERONESE, AUGUSTO C.、GANDOLFI, VITTORIO、BASATO, MARINO、CORAIN, BENEDETTO

  DOI：——

  日期：——
• A new simple route for the synthesis of (±)-2-azetidinones starting from β-enaminoketoesters
  作者：Carmela De Risi、Gian Piero Pollini、Augusto C Veronese、Valerio Bertolasi

  DOI：10.1016/s0040-4020(01)01036-5

  日期：2001.12

  beta -Enaminoketoesters 1, obtained through metal-catalysed reaction of methyl acetoacetate with alkyl cyanoformates have been conveniently transformed into beta -aminoesters 4, 5 by reduction of both the carbonyl group and the carbon-carbon double bond of the enaminoester moiety. These intermediates could be easily converted to (+/-)-2-azetidinones 6, 7 structurally related to thienamycin in good yield and high diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.
• A new simple route for the synthesis of (±)-2-azetidinones starting from β-Enaminoketoesters
  作者：Carmela De Risi、Gian P. Pollini、Augusto C. Veronese、Valerio Bertolasi

  DOI：10.1016/s0040-4039(99)01421-5

  日期：1999.9

  beta-Enaminoketoesters, obtained by metal-catalyzed reaction between alkyl acetoacetates and alkyl cyanoformates, are useful starting materials for rapid access to beta-acetyl-dehydroaspartic acrid derivatives which could be transformed into (+/-)-2-azetidinones bearing a 1-hydroxy-ethyl substituent through suitable reductive processes. (C) 1999 Elsevier Science Ltd. All rights reserved.