N-(3,5-dinitrobenzoyl)-L-leucine methyl ester | 86091-69-2

• 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: N-(3,5-dinitrobenzoyl)-L-leucine methyl ester
• 英文别名: methyl (2S)-2-[(3,5-dinitrobenzoyl)amino]-4-methylpentanoate
• CAS: 86091-69-2
• 化学式: C₁₄H₁₇N₃O₇
• mdl: MFCD00382774
• 分子量: 339.305
• InChiKey: IFCHCEHVZJTNTP-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  147
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (R,S)-N-(3,5-dinitrobenzoyl)-leucine methyl ester 、 (S)-(-)-2-[丙氨基羰酰氧基]丙酸 生成 N-(3,5-dinitrobenzoyl)-L-leucine methyl ester
  参考文献：
  名称：

  SALVADORI, P.;PINI, D.;ROSINI, C.;UCCELLO-BARRETTA, G.;BERTUCCI, C., J. CHROMATOGR., 450,(1988) N 2, C. 163-168

  摘要：

  DOI：

文献信息

• 3,5-dinitrobenzoyl amino acid esters. Broadly applicable chiral solvating agents for NMR determination of enantiomeric purity.
  作者：William H. Pirkle、Athanasios Tsipouras

  DOI：10.1016/s0040-4039(00)98599-x

  日期：1985.1

  Methyl esters of N-(3,5-dinitrobenzoyl)-amino acids have been used as chiral solvating agents to induce NMR spectral nonequivalence between the enantiomers of a broad array of solutes.

  N-（3,5-二硝基苯甲酰基）-氨基酸的甲基酯已被用作手性溶剂化剂，以诱导各种溶质的对映异构体之间的NMR光谱不等价。
• Clay Column Chromatography for Optical Resolution: A Series of Derivatized Amino Acids
  作者：Akihiko Yamagishi、Shohei Yamamoto、Kazuyoshi Takimoto、Kenji Tamura、Masumi Kamon、Fumi Sato、Hisako Sato

  DOI：10.1246/bcsj.20220077

  日期：2022.6.15

  Chromatographic resolution of a series of derivatized amino acids was attempted on a column packed with an ion-exchange adduct of Δ-[Ru(phen)3]2+ (phen = 1,10-phenanthroline) and synthetic hectorite. An amino acid was modified to N-3, 5-dinitrobenzoyl amino acid methyl ester (denoted by DNB-aa-me). For aa = Ala, Phe, Leu, Ile, Ser, Val, Thr, Tyr, Asp and Glu, racemic DNB-aa-me was resolved nearly to

  在填充有 Δ-[Ru(phen) 3 ] 2+ (phen = 1,10-phenanthroline) 和合成锂蒙脱石的离子交换加合物的色谱柱上尝试了一系列衍生氨基酸的色谱分离。将氨基酸修饰为N -3, 5-二硝基苯甲酰基氨基酸甲酯（记作DNB-aa-me）。对于 aa = Ala、Phe、Leu、Ile、Ser、Val、Thr、Tyr、Asp 和 Glu，在用甲醇洗脱时，外消旋 DNB-aa-me 几乎被分离到基线分离。对于 aa = Trp 和 His，外消旋 DNB-aa-me 部分分离。Pro 和 Lys 没有达到分辨率。通过固态振动圆二色光谱研究了手性鉴别的机理。
• Biphasic enantioselective partitioning studies using small-molecule chiral selectors
  作者：Seth E. Snyder、James R. Carey、William H. Pirkle

  DOI：10.1016/j.tet.2005.05.060

  日期：2005.8

  Enantioselective partitioning of racemic N-3,5-(dinitrobenzoyl)leucine or racemic naproxen was studied using a two-component chiral phase transfer approach. A combination of an achiral ion-pairing reagent and a chiral complexing agent (selector) is necessary to effect enantioselective partitioning between an aqueous bicarbonate solution and a nonpolar organic solvent. In these biphasic resolutions, the interplay between the ion-pairing reagent and the selector is essential for maximizing enantioselectivities. Furthermore, the lipophilicity of the ion-pairing reagent, the concentration of the ion-pairing reagent and selector, and the polarity of the organic solvent all exert a considerable influence on the biphasic process. In this manuscript, we conduct optimization studies through analysis of solvent, concentration and ion-pairing effects. Conclusions concerning the mechanistic rationale behind enantioselective partitioning are given. (c) 2005 Elsevier Ltd. All rights reserved.
• Enantioselective and Diastereoselective Binding Study of Silica Bound Macrobicyclic Receptors by HPLC
  作者：Francesco Gasparrini、Domenico Misiti、W. Clark Still、Claudio Villani、Helma Wennemers

  DOI：10.1021/jo962273b

  日期：1997.11.1
• Enantioselective Hydrolysis of N-Acylated α-Amino Esters at a Biphasic Interface:  Tandem Reaction Kinetic Resolution Using a Chiral Complexing Agent
  作者：Seth E. Snyder、William H. Pirkle

  DOI：10.1021/ol026517s

  日期：2002.9.1

  Highly enantioselective hydrolytic kinetic resolutions of esters derived from N-acylated alpha-amino acids proceed rapidly at hydorcarbon/water interfaces in the presence of a proline-derived chiral selector. When performed in tandem with an enantioselective biphasic esterification reaction, esters of 100% enantiomeric excess are obtained.