tert-butyl 2-[2-(2-tert-butoxy-2-oxoethylcarbamoyl)-5-methylhex-2-enamido]acetate | 1255516-66-5

• 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: tert-butyl 2-[2-(2-tert-butoxy-2-oxoethylcarbamoyl)-5-methylhex-2-enamido]acetate
• 英文别名: rGly(O-t-Bu)-mΔ²Leu-Gly(O-t-Bu)；Tert-butyl 2-[[5-methyl-2-[[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]carbamoyl]hex-2-enoyl]amino]acetate；tert-butyl 2-[[5-methyl-2-[[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]carbamoyl]hex-2-enoyl]amino]acetate
• CAS: 1255516-66-5
• 化学式: C₂₀H₃₄N₂O₆
• 分子量: 398.5
• InChiKey: ZVDMAGIMAPYYAN-UHFFFAOYSA-N

物化性质

• 沸点：
  586.6±50.0 °C(predicted)
• 密度：
  1.072±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-[2-(2-tert-butoxy-2-oxoethylcarbamoyl)-5-methylhex-2-enamido]acetate 在 sodium tungstate (VI) dihydrate 、 双氧水 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以98%的产率得到Tert-butyl 2-[[2-[[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]carbamoyl]-3-(2-methylpropyl)oxirane-2-carbonyl]amino]acetate
  参考文献：
  名称：

  Synthesis of epoxy and aziridino malonyl peptidomimetics

  摘要：

  Short malonyl dehydro peptides have been epoxidized using H2O2/Na2WO4 dihydrate. The obtained diastereomeric epoxides were separated by HPLC and successfully tested in the ring opening reaction with N-Boc L-cysteine methyl ester, to indicate their electrophilic behavior. Moreover, by a simple two-step reaction, the epoxy malonyl peptides can be converted into the corresponding aziridino malonyl peptides. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.09.097
• 作为产物：
  描述：

  rGly(O-t-Bu)-mGly-Gly(O-t-Bu) 、 异戊醛 在 哌啶 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以95%的产率得到tert-butyl 2-[2-(2-tert-butoxy-2-oxoethylcarbamoyl)-5-methylhex-2-enamido]acetate
  参考文献：
  名称：

  Short malonyl dehydro peptides as potential scaffolds for peptidomimetics by an efficient Knoevenagel reaction

  摘要：

  Non-symmetric disubstituted malonamides rAA-mGly-AA', obtained from Meldrum's acid, were considered as methylene active compounds and a Knoevenagel condensation methodology was developed involving piperidine and activated 4 molecular sieves as catalysts. The reaction is efficient, broad in scope, and easy to perform and allows access to E/Z mixtures of short malonyl dehydro peptides (MDHPs) rAA-m Delta(2)AAaEuro(3)-AA', partially modified retro peptides characterized by an interesting combination of retro and dehydro modifications in the same structure.

  DOI：

  10.1007/s00726-009-0462-1

文献信息

• Short malonyl dehydro peptides as potential scaffolds for peptidomimetics by an efficient Knoevenagel reaction
  作者：Stefania Fioravanti、Simona Gasbarri、Alberto Morreale、Lucio Pellacani、Federico Ramadori、Paolo A. Tardella

  DOI：10.1007/s00726-009-0462-1

  日期：2010.7

  Non-symmetric disubstituted malonamides rAA-mGly-AA', obtained from Meldrum's acid, were considered as methylene active compounds and a Knoevenagel condensation methodology was developed involving piperidine and activated 4 molecular sieves as catalysts. The reaction is efficient, broad in scope, and easy to perform and allows access to E/Z mixtures of short malonyl dehydro peptides (MDHPs) rAA-m Delta(2)AAaEuro(3)-AA', partially modified retro peptides characterized by an interesting combination of retro and dehydro modifications in the same structure.
• Synthesis of epoxy and aziridino malonyl peptidomimetics
  作者：Stefania Fioravanti、Simona Gasbarri、Lucio Pellacani、Federico Ramadori、Paolo A. Tardella

  DOI：10.1016/j.tet.2010.09.097

  日期：2010.11

  Short malonyl dehydro peptides have been epoxidized using H2O2/Na2WO4 dihydrate. The obtained diastereomeric epoxides were separated by HPLC and successfully tested in the ring opening reaction with N-Boc L-cysteine methyl ester, to indicate their electrophilic behavior. Moreover, by a simple two-step reaction, the epoxy malonyl peptides can be converted into the corresponding aziridino malonyl peptides. (C) 2010 Elsevier Ltd. All rights reserved.