N-(2-aminobenzoyl)-S-valine methyl ester | 115616-17-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-aminobenzoyl)-S-valine methyl ester
• 英文别名: methyl (2-aminobenzoyl)valinate；methyl (2-aminobenzoyl)-L-valinate；methyl (2S)-2-[(2-aminobenzoyl)amino]-3-methylbutanoate
• CAS: 115616-17-6
• 化学式: C₁₃H₁₈N₂O₃
• mdl: MFCD13283094
• 分子量: 250.298
• InChiKey: BESOUTWBUBKRFG-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  81.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-aminobenzoyl)-S-valine methyl ester 在 吡啶 、 palladium 10% on activated carbon 、 氢气 、 三氯氧磷 作用下， 以 乙醇 、 水 为溶剂， 反应 10.0h， 生成 (S)-methyl 3-methyl-2-(2-((S)-pyrrolidine-2-carboxamido)benzamido)butanoate
  参考文献：
  名称：

  N-Prolinylanthranilamide Pseudopeptides as Bifunctional Organocatalysts for Asymmetric Aldol Reactions

  摘要：

  Proline anthranilamide-based pseudopeptides were shown to be effective organocatalysts for enantioselective direct aldol reactions of a selection of aldehydes with various ketones with excellent yield, enantioselectivity up to 99% and anti to syn diastereoselectivity up to 25:1.

  DOI：

  10.1021/ol202284n
• 作为产物：
  描述：

  L-缬氨酸甲酯 在 palladium on activated charcoal 氢气 、 碳酸氢钠 作用下， 以 甲醇 、 水 、 乙酸乙酯 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

文献信息

• Facile synthesis of 1,4-benzodiazepine-2,5-diones and quinazolinones from amino acids as anti-tubercular agents
  作者：Seegehalli M. Anil、Rangappa Shobith、Kuppalli. R. Kiran、Toreshettahally R. Swaroop、Ningegowda Mallesha、Maralinganadoddi P. Sadashiva

  DOI：10.1039/c8nj04936j

  日期：——

  The results revealed that the 1,4-benzodiazepine-2,5-diones displayed promising activity in comparison with their open chain precursors, which indicates that the diazepine frame is vital for their activity. The compounds 4h and 4f were found to be the lead nominees in the series with MIC values of 1.55 and 2.87 μg mL−1, respectively. A docking study was carried out on the enoyl acyl carrier protein to

  使用H 2 PtCl 6作为催化剂，通过新颖，简单，方便的方法合成了在C-3位具有多个取代基的1,4-苯并二氮杂-2,5-二酮和喹唑啉酮类。使用预定的氨基酸作为前体来改变C-3位上的取代。筛选合成的苯二氮卓类药物的抗分枝杆菌结核病（抗结核病）活性。结果显示，与它们的开链前体相比，1,4-苯并二氮杂-2,5-二酮显示出有希望的活性，这表明二氮杂骨架对其活性至关重要。发现化合物4h和4f是该系列中的主要被提名人，MIC值为1.55和2.87μgmL-1。对烯酰基酰基载体蛋白进行了对接研究，以更好地理解这些化合物的作用机理。根据这项研究，1,4-苯并二氮杂-2,5-二酮构架是开发治疗多种药物耐药性结核病的新先导药物候选药物的良好起点。
• Synthesis of Some New Chiral Sulfonamide Ligands
  作者：Lucia Z. Flores-López、Miguel Parra-Hake、Ratnasamy Somanathan、Fernando Ortega、Gerardo Aguirre

  DOI：10.1080/00397910008087302

  日期：2000.1

  Synthesis of new chiral sulfonamide ligands derived from isatoic anhydride by reaction with trans-(R,R)-1,2-diaminocyclohexane and chiral aminoacid esters.
• <i>N</i>-Prolinylanthranilamide Pseudopeptides as Bifunctional Organocatalysts for Asymmetric Aldol Reactions
  作者：Anthony J. Pearson、Santanu Panda

  DOI：10.1021/ol202284n

  日期：2011.10.21

  Proline anthranilamide-based pseudopeptides were shown to be effective organocatalysts for enantioselective direct aldol reactions of a selection of aldehydes with various ketones with excellent yield, enantioselectivity up to 99% and anti to syn diastereoselectivity up to 25:1.
• 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.