ethyl 2-[(N-benzyloxycarbonyl)-amino]-3-methoxycarbonyl-4-oxo-2-pentenoate | 401630-59-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-[(N-benzyloxycarbonyl)-amino]-3-methoxycarbonyl-4-oxo-2-pentenoate
• 英文别名: 1-O-ethyl 4-O-methyl (E)-3-acetyl-2-(phenylmethoxycarbonylamino)but-2-enedioate
• CAS: 401630-59-9
• 化学式: C₁₇H₁₉NO₇
• 分子量: 349.34
• InChiKey: PNVWQGTXMKOMCM-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(N-benzyloxycarbonyl)-amino]-3-methoxycarbonyl-4-oxo-2-pentenoate 在 Ni Raney W-2 咪唑 、 sodium tetrahydroborate 、 叔丁基氯化镁 、 氢气 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.17h， 生成 (+/-)-3-[(1-tert-butyldimethylsilyloxy)-ethyl]-4-ethoxycarbonyl-azetidin-2-one
  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：

  氯甲酸苄酯 、 ethyl 2-amino-3-methoxycarbonyl-4-oxo-2-pentanoate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以71%的产率得到ethyl 2-[(N-benzyloxycarbonyl)-amino]-3-methoxycarbonyl-4-oxo-2-pentenoate
  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 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.
• 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.