(R)-2-Amino-4-methyl-pentanoic acid benzylamide | 123636-09-9

• 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: (R)-2-Amino-4-methyl-pentanoic acid benzylamide
• 英文别名: (2R)-2-amino-N-benzyl-4-methylpentanamide
• CAS: 123636-09-9
• 化学式: C₁₃H₂₀N₂O
• 分子量: 220.315
• InChiKey: LFEKGCDQYKTXGA-GFCCVEGCSA-N

物化性质

• 沸点：
  400.8±38.0 °C(Predicted)
• 密度：
  1.023±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-Amino-4-methyl-pentanoic acid benzylamide 在 氯甲酸乙酯 、 sodium cyanoborohydride 、 sodium sulfate 、 三乙胺 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 25.67h， 生成 (3R)-4-[((1R)-1-benzylcarbamoyl-3-methyl-butyl)carbamoyl]-3-phenyl-butyric acid ethyl ester
  参考文献：
  名称：

  Circular dichroism studies on absolute configuration assignment of peptidomimetics with a terminal chiral 3-arylpropionic acid unit

  摘要：

  The relationship between the molecular structure of peptidomimetics 1 and their chiroptical properties has been studied using circular dichroism spectroscopy. It was demonstrated that the sign of the Cotton effects occurring around 230 and 270 nm enables the direct assignment of stereochemistry at C-1 and C-3 carbon atoms. The TD-DFT calculations of the circular dichroisin (CD) spectrum of one of the model compounds confirm the absolute stereochemistry assignment made experimentally. Thus, CD spectroscopy proved to be a simple, reliable and general tool for the determination of the absolute configuration of the stereogenic centers of peptidomimetics with a terminal 3-arylpropionic group. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.08.024
• 作为产物：
  描述：

  methyl (1S,2S,3S,4R)-3-[benzyl-[(2R)-1-(benzylamino)-4-methyl-1-oxopentan-2-yl]amino]-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylate 在 钯 盐酸 、 甲酸 作用下， 以 1,4-二氧六环 、 甲醇 、 甲苯 为溶剂， 反应 6.0h， 生成 (R)-2-Amino-4-methyl-pentanoic acid benzylamide
  参考文献：
  名称：

  一种新型的高选择性手性助剂，通过多组分Ugi反应不对称合成l-和d-α-氨基酸衍生物

  摘要：

  本文描述了纯对映体形式的双环β-氨基酸支架的合成及其在Ugi多组分反应（U-5C-4CR）的分子内形式中的手性助剂的制备，以制备两种d的α-氨基酸衍生物-和l系列以直接且非常立体选择性的方式。Ugi缩合和除去手性助剂所需的温和条件使该方法对于制备各种不同结构的N-烷基化和未烷基化的氨基酸衍生物非常有吸引力。

  DOI：

  10.1021/jo048389m

文献信息

• Liquid Chromatographic Resolution of Tocainide and Its Analogues on a Doubly Tethered Chiral Stationary Phase Based on (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic Acid
  作者：Hee-Jin Kim、Hee-Jung Choi、Myung-Ho Hyun

  DOI：10.5012/bkcs.2010.31.03.678

  日期：2010.3.20

  A doubly tethered chiral stationary phase (CSP) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid were appli- ed to the liquid chromatographic resolution of racemic tocainide, an antiarrhythmic agent, and its analogues. The chiral recognition efficiency of the doubly tethered CSP for tocainide and its analogues was generally greater than that of the corresponding singly tethered CSP especially

  将基于 (+)-(18-crown-6)-2,3,11,12-四羧酸的双键手性固定相 (CSP) 应用于抗心律失常药物外消旋妥卡尼的液相色谱分离中，及其类似物。双束缚 CSP 对妥卡尼及其类似物的手性识别效率通常高于相应的单束缚 CSP，尤其是在分辨率 (RS) 方面。托卡尼及其类似物在双束缚 CSP 上的分离度取决于水性流动相中有机和酸性改性剂的含量和类型以及柱温。尤其，
• Protecting-Group-Free Amidation of Amino Acids using Lewis Acid Catalysts
  作者：Marco T. Sabatini、Valerija Karaluka、Rachel M. Lanigan、Lee T. Boulton、Matthew Badland、Tom D. Sheppard

  DOI：10.1002/chem.201800372

  日期：2018.5.11

  Amidation of unprotected amino acids has been investigated using a variety of ‘classical“ coupling reagents, stoichiometric or catalytic group(IV) metal salts, and boron Lewis acids. The scope of the reaction was explored through the attempted synthesis of amides derived from twenty natural, and several unnatural, amino acids, as well as a wide selection of primary and secondary amines. The study also

  已使用多种“经典”偶联剂，化学计量或催化基团（IV）金属盐和硼路易斯酸研究了未保护氨基酸的酰胺化。通过尝试合成衍生自二十种天然和几种非天然氨基酸以及广泛选择的伯胺和仲胺的酰胺，探索了反应的范围。该研究还研究了药用相关化合物的合成，以及这种直接酰胺化方法的可扩展性。最后，我们提供了对在这些反应中观察到的化学选择性的见解。
• [EN] NOVEL CYCLIC TREX1 INHIBITORS<br/>[FR] NOUVEAUX INHIBITEURS CYCLIQUES DE TREX1
  申请人：VENENUM BIODESIGN LLC

  公开号：WO2020210032A1

  公开（公告）日：2020-10-15

  The present invention provides compounds of Formula I: wherein, X, R1, R2, R3 and R4 are as defined herein, or a stereoisomer, tautomer, pharmaceutically acceptable salt, prodrug ester or solvate form thereof, wherein all of the variables are as defined herein. These compounds are effective at modulating the TREX1 protein and thus can be used as medicaments for treating or preventing disorders affected by the inhibition of TREX1.

  本发明提供了化合物的结构如下：其中，X、R1、R2、R3和R4的定义如本文所述，或其立体异构体、互变异构体、药学上可接受的盐、前药酯或溶剂化合物形式，其中所有变量均如本文所述。这些化合物能有效调节TREX1蛋白，因此可用作治疗或预防受TREX1抑制影响的疾病的药物。
• Substituted pyrrolo[1,2-a]pyrazines and pyrrolo[1,2-a][1,4]diazepines as TREX1 inhibitors
  申请人：VENENUM BIODESIGN, LLC

  公开号：US11306098B2

  公开（公告）日：2022-04-19

  The present invention provides compounds of Formula I wherein X, R1, R2, R3 and R4 are as defined herein, or a stereoisomer, tautomer, pharmaceutically acceptable salt, prodrug ester or solvate form thereof, wherein all of the variables are as defined herein. These compounds are effective at modulating the TREX1 protein and thus can be used as medicaments for treating or preventing disorders affected by the inhibition of TREX1.

  本发明提供了式 I 的化合物 其中 X、R1、R2、R3 和 R4 如本文所定义，或其立体异构体、同系物、药学上可接受的盐、原药酯或溶 剂形式，其中所有变量如本文所定义。这些化合物能有效调节 TREX1 蛋白，因此可用作治疗或预防受 TREX1 抑制影响的疾病的药物。
• NOVEL CYCLIC TREX1 INHIBITORS
  申请人：VENENUM BIODESIGN, LLC

  公开号：US20200317677A1

  公开（公告）日：2020-10-08

  The present invention provides compounds of Formula I wherein X, R 1 , R 2 , R 3 and R 4 are as defined herein, or a stereoisomer, tautomer, pharmaceutically acceptable salt, prodrug ester or solvate form thereof, wherein all of the variables are as defined herein. These compounds are effective at modulating the TREX1 protein and thus can be used as medicaments for treating or preventing disorders affected by the inhibition of TREX1.