2-Methylpropoxycarbonyl 2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate | 109208-68-6

• 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: 2-Methylpropoxycarbonyl 2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 109208-68-6；127476-50-0
• 化学式: C₁₃H₂₃NO₆
• 分子量: 289.329
• InChiKey: JNYNOOFBKFYQIE-UHFFFAOYSA-N

物化性质

• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-Methylpropoxycarbonyl 2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate 在 N-甲基吗啉 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 3-(4-Bromo-phenyl)-2-(2-tert-butoxycarbonylamino-propionylamino)-propionic acid
  参考文献：
  名称：

  Chloramines VII:  Chlorination of Alanylphenylalanine in Model Solutions and in a Wastewater

  摘要：

  Products of the 30-min chlorination of the dipeptide alanylphenylalanine were determined at pH 7.0 in model solutions. At Cl-2/peptide mole ratios less than or equal to 1, N-chloroalanylphenylalanine (I) is the only product. I is very stable at 23 degrees C (t(1/2) = 111 +/- 8.8 h). At mole ratios greater than or equal to 2, N,N-dichloroalanylphenylalanine (II) is the only product. II decomposes in model solutions (t(1/2) = 4.1 +/- 0.2 h) at pH 7.0 to form a compound identified as the N-chloroketimine N-[2-(N'-chloroimino)propanoyl]phenylalanine (III). The structure of III was identified by converting it to N-pyruvylphenylalanine tert-butyl ester by reduction, hydrolysis, and esterification and correlating the mass spectrum and GC retention time of this derivative with those of an authentic sample. III is unusually stable and decomposes slowly (t(1/2) = 125 +/- 6.5 h) to phenylalanine. In order to monitor the reactions of the dipeptide at low concentrations in a wastewater, alanyl-p-[H-3]-phenylalanine was synthesized. A primary wastewater (TKN = 19.82 mg/L; [NH3] = 19.79 mg/L) was inoculated with the radiolabeled dipeptide and chlorinated to seven different chlorine concentrations spanning the breakpoint curve of the wastewater. Products identical to those observed in model solutions were formed. The stabilities of the tritiated analogs of II and III in the wastewater were similar to those determined in model solutions. Time studies of the decomposition of N,N-dichloroalanyl-p-[H-3]-phenylalanine revealed the formation of an intermediate (A) not previously recognized. Modeling of the reactions of II suggested that A was a decomposition product of III in the formation of phenylalanine and was probably either an isocyanate or a carbamic acid formed from hydrolysis of an isocyanate intermediate.

  DOI：

  10.1021/es9607953
• 作为产物：
  描述：

  BOC-DL-丙氨酸 、 氯甲酸异丁酯 在 N-甲基吗啉 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 2-Methylpropoxycarbonyl 2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
  参考文献：
  名称：

  Bertram, Anna; Pattenden, Gerald, Heterocycles, 2002, vol. 58, p. 521 - 561

  摘要：

  DOI：

文献信息

• Solution-phase synthesis of novel seven-membered cyclic dipeptides containing α- and β-amino acids
  作者：Erika Jiménez-González、C. Gabriela Ávila-Ortiz、Rodrigo González-Olvera、Jorge Vargas-Caporali、Georges Dewynter、Eusebio Juaristi

  DOI：10.1016/j.tet.2012.08.050

  日期：2012.11

  for the preparation of seven-membered cyclic α,β-dipeptides is described. Following coupling of N-protected α-amino acids with N-substituted β-amino acid tert-butyl esters, that affords linear α,β-dipeptides, the protecting groups at the terminal functionalities were removed and the open-chain dipeptides were cyclized with phenylphosphonic dichloride, PhP(O)Cl2, to give the desired cyclic α,β-dipeptides

  描述了一种方便的合成方法，用于制备七元环状α，β-二肽。N-保护的α-氨基酸与N-取代的β-氨基酸叔丁酯偶联后，得到线性的α，β-二肽，末端官能团上的保护基被除去，开环二肽用苯基膦二氯化物PhP（O）Cl 2，以良好的收率得到所需的环状α，β-二肽。NMR研究，X射线衍射分析和DFT计算为这些环状二肽在溶液，固态和气相中所采用的构象提供了证据。
• Efficient microwave-assisted two-step procedure for the synthesis of 1,3-disubstituted-imidazo[1,5-a]quinazolin-5-(4H)-ones
  作者：Flavia Jankowski、Valérie Verones、Nathalie Flouquet、Pascal Carato、Pascal Berthelot、Nicolas Lebegue

  DOI：10.1016/j.tet.2009.11.025

  日期：2010.1

  A general method has been developed for the synthesis of 1,3-disubstituted-imidazo[1,5-a]quinazolin-5-(4H)-ones. This process involves initial microwave-assisted quinazolinone formation between anthranilamide and various Boc- or acylamino acids, followed by intramolecular cyclodehydration under acidic conditions. In the case of 3-monosubstituted-imidazoquinazolinones, the procedure needs the formation

  已经开发了一种用于合成1，3-二取代-咪唑并[1，5-a]喹唑啉-5-（4H）-的通用方法。该过程涉及蒽酰胺与各种Boc或酰基氨基酸之间最初的微波辅助喹唑啉酮形成，然后在酸性条件下进行分子内环脱水。对于3-单取代的咪唑并喹唑啉酮，该过程需要通过Boc中间体的脱保护和甲酰化来形成甲酰胺衍生物。
• Peptide conformational distributions as studied by electron-transfer kinetics
  作者：Mark S. Meier、Marye Anne Fox、John R. Miller

  DOI：10.1021/jo00018a034

  日期：1991.8

  The preparation and electron-transfer (ET) behavior of a homologous series of alanine oligomers bearing naphthoyl groups at the N-termini and biphenylylamide groups at the C-termini is described. Electron pulse radiolysis was used to generate the corresponding radical anions, and the rates of ET were monitored at 700 nm (decay of donor) and at 500 nm (growth of acceptor). Several systems displayed ET decays too fast to measure (k(et) > 10(10)), and in the others multiexponential decay kinetics were observed. The ET decay of dipeptide 3 could be fit to two exponential described by rate constants of 5.2 x 10(8) (22%) and 5.6 x 10(9) s-1 (78%). In the longer peptides, the fit of the rate constants (and their relative contributions to total intensity) becomes less well-defined, suggesting additional conformational diversity.
• Bertram, Anna; Pattenden, Gerald, Heterocycles, 2002, vol. 58, p. 521 - 561
  作者：Bertram, Anna、Pattenden, Gerald

  DOI：——

  日期：——
• Chloramines VII:  Chlorination of Alanylphenylalanine in Model Solutions and in a Wastewater
  作者：T. Christopher Fox、Daniel J. Keefe、Frank E. Scully、A. Laikhter

  DOI：10.1021/es9607953

  日期：1997.7.1

  Products of the 30-min chlorination of the dipeptide alanylphenylalanine were determined at pH 7.0 in model solutions. At Cl-2/peptide mole ratios less than or equal to 1, N-chloroalanylphenylalanine (I) is the only product. I is very stable at 23 degrees C (t(1/2) = 111 +/- 8.8 h). At mole ratios greater than or equal to 2, N,N-dichloroalanylphenylalanine (II) is the only product. II decomposes in model solutions (t(1/2) = 4.1 +/- 0.2 h) at pH 7.0 to form a compound identified as the N-chloroketimine N-[2-(N'-chloroimino)propanoyl]phenylalanine (III). The structure of III was identified by converting it to N-pyruvylphenylalanine tert-butyl ester by reduction, hydrolysis, and esterification and correlating the mass spectrum and GC retention time of this derivative with those of an authentic sample. III is unusually stable and decomposes slowly (t(1/2) = 125 +/- 6.5 h) to phenylalanine. In order to monitor the reactions of the dipeptide at low concentrations in a wastewater, alanyl-p-[H-3]-phenylalanine was synthesized. A primary wastewater (TKN = 19.82 mg/L; [NH3] = 19.79 mg/L) was inoculated with the radiolabeled dipeptide and chlorinated to seven different chlorine concentrations spanning the breakpoint curve of the wastewater. Products identical to those observed in model solutions were formed. The stabilities of the tritiated analogs of II and III in the wastewater were similar to those determined in model solutions. Time studies of the decomposition of N,N-dichloroalanyl-p-[H-3]-phenylalanine revealed the formation of an intermediate (A) not previously recognized. Modeling of the reactions of II suggested that A was a decomposition product of III in the formation of phenylalanine and was probably either an isocyanate or a carbamic acid formed from hydrolysis of an isocyanate intermediate.