methyl 5-oxo-2-(tert-butoxycarbonylamino)hept-6-enoate | 871691-85-9

• 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 5-oxo-2-(tert-butoxycarbonylamino)hept-6-enoate
• 英文别名: methyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxohept-6-enoate
• CAS: 871691-85-9
• 化学式: C₁₃H₂₁NO₅
• 分子量: 271.313
• InChiKey: YTJMPSOEKYOVLX-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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 5-oxo-2-(tert-butoxycarbonylamino)hept-6-enoate 在 palladium on activated charcoal 三乙基硅烷 、 氢气 、 sodium carbonate 、 caesium carbonate 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 25.0h， 生成 (3S,6S,9S)-2-oxo-3-(N-(9-fluorenylmethoxycarbonyl)amino)-1-azabicyclo[4.3.0]nonane-9-carboxylic acid
  参考文献：
  名称：

  An Efficient Synthesis of the Constrained Peptidomimetic 2-Oxo-3-(N-9-fluorenyloxy-carbonylamino)-1-azabicyclo[4.3.0]nonane-9-carboxylic Acid from Pyroglutamic Acid

  摘要：

  Azabicyclo[X.Y.0]alkane amino acids are rigid dipeptide mimetics that are useful tools for structure-activity studies in peptide-based drug discovery. Herein, we report an efficient synthesis of three diastereomers of 9-tert-butoxycarbonyl-2-oxo-3-(N-tert-butoxycarbonylamino)-1-azabicyclo- [4.3.0]nonane (3S,6S,9S, 3S,6R,9R, and 3S,6R,9S). Methyl N-Boc-pyroglutamate is cleaved with vinylmagnesium bromide to produce an acyclic gamma-vinyl ketone. Michael addition of N-diphenylmethyleneglycine tert-butyl ester produces the N-Boc-delta-oxo-alpha,omega-diaminoazelate intermediate, which, on hydrogenloysis, gives the fused ring system. Acidolytic deprotection followed by Fmoc-protection provided building blocks suitable for solid-phase synthesis.

  DOI：

  10.1021/jo0515935
• 作为产物：
  描述：

  乙烯基溴化镁 、 Boc-L-焦谷氨酸甲酯 以 四氢呋喃 为溶剂， 反应 3.0h， 以80%的产率得到methyl 5-oxo-2-(tert-butoxycarbonylamino)hept-6-enoate
  参考文献：
  名称：

  An Efficient Synthesis of the Constrained Peptidomimetic 2-Oxo-3-(N-9-fluorenyloxy-carbonylamino)-1-azabicyclo[4.3.0]nonane-9-carboxylic Acid from Pyroglutamic Acid

  摘要：

  Azabicyclo[X.Y.0]alkane amino acids are rigid dipeptide mimetics that are useful tools for structure-activity studies in peptide-based drug discovery. Herein, we report an efficient synthesis of three diastereomers of 9-tert-butoxycarbonyl-2-oxo-3-(N-tert-butoxycarbonylamino)-1-azabicyclo- [4.3.0]nonane (3S,6S,9S, 3S,6R,9R, and 3S,6R,9S). Methyl N-Boc-pyroglutamate is cleaved with vinylmagnesium bromide to produce an acyclic gamma-vinyl ketone. Michael addition of N-diphenylmethyleneglycine tert-butyl ester produces the N-Boc-delta-oxo-alpha,omega-diaminoazelate intermediate, which, on hydrogenloysis, gives the fused ring system. Acidolytic deprotection followed by Fmoc-protection provided building blocks suitable for solid-phase synthesis.

  DOI：

  10.1021/jo0515935

文献信息

• An Efficient Synthesis of the Constrained Peptidomimetic 2-Oxo-3-(<i>N</i>-9-fluorenyloxy-carbonylamino)-1-azabicyclo[4.3.0]nonane-9-carboxylic Acid from Pyroglutamic Acid
  作者：Pijus Kumar Mandal、Kumar K. Kaluarachchi、Douglas Ogrin、Simon G. Bott、John S. McMurray

  DOI：10.1021/jo0515935

  日期：2005.11.1

  Azabicyclo[X.Y.0]alkane amino acids are rigid dipeptide mimetics that are useful tools for structure-activity studies in peptide-based drug discovery. Herein, we report an efficient synthesis of three diastereomers of 9-tert-butoxycarbonyl-2-oxo-3-(N-tert-butoxycarbonylamino)-1-azabicyclo- [4.3.0]nonane (3S,6S,9S, 3S,6R,9R, and 3S,6R,9S). Methyl N-Boc-pyroglutamate is cleaved with vinylmagnesium bromide to produce an acyclic gamma-vinyl ketone. Michael addition of N-diphenylmethyleneglycine tert-butyl ester produces the N-Boc-delta-oxo-alpha,omega-diaminoazelate intermediate, which, on hydrogenloysis, gives the fused ring system. Acidolytic deprotection followed by Fmoc-protection provided building blocks suitable for solid-phase synthesis.