3-methyl-2-(2-nitro-benzoylamino)butyric acid methyl ester | 27262-02-8

• 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: 3-methyl-2-(2-nitro-benzoylamino)butyric acid methyl ester
• 英文别名: methyl (2S)-3-methyl-2-[(2-nitrobenzoyl)amino]butanoate
• CAS: 27262-02-8
• 化学式: C₁₃H₁₆N₂O₅
• 分子量: 280.28
• InChiKey: SCVIRXRHPMRMGK-NSHDSACASA-N

物化性质

• 沸点：
  439.3±30.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-methyl-2-(2-nitro-benzoylamino)butyric acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 N-(2-aminobenzoyl)-S-valine methyl ester
  参考文献：
  名称：

  Synthesis and structure of chiral 2,6-bis[(2-carbamoylphenyl)carbamoyl]pyridine ligands

  摘要：

  The synthesis and structure of a series of enantiomerically pure 2,6-bis[(2-carbamoylphenyl)carbamoyl]-pyridine ligands (H(2)a-c) are described. Appended from the aryl groups are optically active groups which provide a chiral environment around the planar pyridine core. NMR and X-ray diffraction studies show that these ligands contain helical character which is maintained by a network of intramolecular hydrogen bonds. These ligands can bind metal ions through their tridentate diamidato-pyridyl chelate to form optically active metal complexes. The modular design of these ligands offers a variety of chiral environments about the metal chelate that can be useful in the synthesis of metal reagents for asymmetric transformations. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01486-5
• 作为产物：
  描述：

  L-缬氨酸甲酯 、 2-硝基苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到3-methyl-2-(2-nitro-benzoylamino)butyric acid methyl ester
  参考文献：
  名称：

  苯胺的催化还原性N-烷基化。在合成N-芳基氨基酸前体中的应用

  摘要：

  使用酮和α-酮酸酯作为烷基化剂，通过还原烷基化将不同的苯胺单烷基化，分离收率很好。这提供了获得氨基酸衍生物的途径。还进行了非对映选择性实验。

  DOI：

  10.1016/0040-4020(96)00503-0

文献信息

• Catalytic reductive N-alkylation of anilines. Application to the synthesis of N-aryl aminoacid precursors
  作者：Fabienne Fache、Frédéric Valot、Alexandra Milenkovic、Marc Lemaire

  DOI：10.1016/0040-4020(96)00503-0

  日期：1996.7

  different anilines have been monoalkylated by reductive alkylation using ketones and α-ketoesters as alkylating agents with good isolated yields. This provided access to aminoacid derivatives. Diastereoselective experiments were also performed.

  使用酮和α-酮酸酯作为烷基化剂，通过还原烷基化将不同的苯胺单烷基化，分离收率很好。这提供了获得氨基酸衍生物的途径。还进行了非对映选择性实验。
• An Improved Aldehyde Linker for the Solid Phase Synthesis of Hindered Amides
  作者：Mark J. Liley、Tony Johnson、Susan E. Gibson

  DOI：10.1021/jo051742j

  日期：2006.2.1

  A novel aldehyde dual-linker system has been developed for the solid phase synthesis of sterically hindered amides. The linker [5-(4-formyl-3-hydroxyphenoxy)pentanoic acid] exploits an intramolecular oxygen−nitrogen acyl transfer mechanism to prepare compounds that are unattainable with current commercially available linkers. A dual linker system, exploiting the hyper-acid labile Sieber amide linker

  已经开发了用于空间位阻酰胺的固相合成的新型醛双接头系统。接头[5-（4-甲酰基-3-羟基苯氧基）戊酸]利用分子内氧-氮酰基酰基转移机理来制备用当前市售接头无法获得的化合物。利用高酸不稳定的Sieber酰胺接头作为构建体的一部分的双接头系统，可以监测受阻胺的初始还原烷基化反应，以及随后被一系列具有不同立体电子性质的羧酸酰化的情况。简单的酰化条件（HBTU / HOBt / NMM）足以提供测试酸与支持物结合的受阻胺的接近定量反应，当使用商业连接子时，该反应条件会失败。
• Synthesis and structure of chiral 2,6-bis[(2-carbamoylphenyl)carbamoyl]pyridine ligands
  作者：Qiang Yu、Timothy E. Baroni、Louise Liable-Sands、Arnold L. Rheingold、A.S. Borovik

  DOI：10.1016/s0040-4039(98)01486-5

  日期：1998.9

  The synthesis and structure of a series of enantiomerically pure 2,6-bis[(2-carbamoylphenyl)carbamoyl]-pyridine ligands (H(2)a-c) are described. Appended from the aryl groups are optically active groups which provide a chiral environment around the planar pyridine core. NMR and X-ray diffraction studies show that these ligands contain helical character which is maintained by a network of intramolecular hydrogen bonds. These ligands can bind metal ions through their tridentate diamidato-pyridyl chelate to form optically active metal complexes. The modular design of these ligands offers a variety of chiral environments about the metal chelate that can be useful in the synthesis of metal reagents for asymmetric transformations. (C) 1998 Elsevier Science Ltd. All rights reserved.