(2S)-环戊基甘氨酸甲酯 | 801162-35-6

• 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
• 中文名称: (2S)-环戊基甘氨酸甲酯
• 英文名称: (2S)-cyclopentyl glycine methyl ester
• 英文别名: cyclopentylglycine methyl ester；L-2-Cyclopentyl-2-amino-essigsaeuremethylester；(S)-Methyl 2-amino-2-cyclopentylacetate；methyl (2S)-2-amino-2-cyclopentylacetate
• CAS: 801162-35-6
• 化学式: C₈H₁₅NO₂
• 分子量: 157.213
• InChiKey: ZGQSMYWOPKCARZ-ZETCQYMHSA-N

物化性质

• 沸点：
  209.6±13.0 °C(Predicted)
• 密度：
  1.062±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (2S)-环戊基甘氨酸甲酯 在 4-二甲氨基吡啶 、 lithium hydroxide monohydrate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 6.0h， 生成 (S)-2-(((((1R,2S)-2-allylcyclopentyl)oxy)carbonyl)amino)-2-cyclopentylacetic acid
  参考文献：
  名称：

  Development of macrocyclic inhibitors of HCV NS3/4A protease with cyclic constrained P2–P4 linkers

  摘要：

  A series of macrocyclic compounds containing a cyclic constraint in the P2-P4 linker region have been discovered and shown to exhibit excellent HCV NS3/4a genotype 3a and genotype 1b R155 K, A156T, A156 V, and D168 V mutant activity while maintaining high rat liver exposure. The effect of the constraint is most dramatic against gt 1b A156 mutants where similar to 20-fold improvements in potency are achieved by introduction of a variety of ring systems into the P2-P4 linker. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.061
• 作为产物：
  描述：

  乙酰基氨基-环戊基-乙酸 在 氯化亚砜 作用下， 生成 (2S)-环戊基甘氨酸甲酯
  参考文献：
  名称：

  Eisler,K. et al., Collection of Czechoslovak Chemical Communications, 1966, vol. 31, p. 4563 - 4580

  摘要：

  DOI：

文献信息

• [EN] SMALL MOLECULE MODULATORS OF IL-17<br/>[FR] MODULATEURS À PETITES MOLÉCULES D'IL-17
  申请人：LEO PHARMA AS

  公开号：WO2021250194A1

  公开（公告）日：2021-12-16

  The present invention relates to a compound according to formula (I), (I) and pharmaceutically acceptable salts, hydrates, or solvates thereof. The invention further relates to said compounds for use in therapy, to pharmaceutical compositions comprising said compounds, to methods of treating diseases, e.g. dermal diseases, with said compounds, and to the use of said compounds in the manufacture of medicaments.

  本发明涉及一种符合式(I)的化合物，以及其药学上可接受的盐、水合物或溶剂合物。该发明还涉及上述化合物在治疗中的应用，包括包含该化合物的药物组合物，用于使用该化合物制造药物的方法，例如用于治疗皮肤病等疾病的方法。
• Highly Efficient Carbamate Formation from Alcohols and Hindered Amino Acids or Esters Using N,N′-Disuccinimidyl Carbonate (DSC)
  作者：Hongmei Li、Cheng-yi Chen、Jaume Balsells Padros

  DOI：10.1055/s-0030-1260584

  日期：2011.6

  A highly efficient and straightforward protocol to prepare carbamates from alcohols and hindered amino acids/esters mediated by N,N′-disuccinimidyl carbonate (DSC) in the presence of catalytic amount of pyridine is described. This method could be carried out under mild conditions in one pot, and a wide variety of carbamates were obtained in high yield with excellent purity.

  本研究介绍了一种在催化量的吡啶存在下，以 N,N′-二琥珀酰亚胺基碳酸酯（DSC）为介导，从醇和受阻氨基酸/酯制备氨基甲酸酯的高效而简单的方法。该方法可在温和的条件下一锅完成，并能以高产率和极高的纯度获得多种氨基甲酸酯。
• Aspartyl β-Turn-Based Dirhodium(II) Metallopeptides for Benzylic C(sp³)–H Amination: Enantioselectivity and X-ray Structural Analysis
  作者：Naudin van den Heuvel、Savannah M. Mason、Brandon Q. Mercado、Scott J. Miller

  DOI：10.1021/jacs.3c03587

  日期：2023.6.7

  significant advances in catalyst design, full site- and enantiocontrol in complex molecular regimes remain elusive using established catalyst systems. To address these challenges, we herein describe a new class of peptide-based dirhodium(II) complexes derived from aspartic acid-containing β-turn-forming tetramers. This highly modular system can serve as a platform for the rapid generation of new chiral dirhodium(II)

  C(sp 3 )–H 键的胺化是将氮直接引入复杂有机框架的有力工具。尽管催化剂设计取得了重大进展，但使用现有的催化剂系统仍然难以实现复杂分子状态的全位点和对映体控制。为了应对这些挑战，我们在此描述了一类新型的基于肽的二铑(II)复合物，其衍生自含天冬氨酸的β-转角形成四聚体。这种高度模块化的系统可以作为快速生成新型手性二铑 (II) 催化剂库的平台，一系列 38 种催化剂的轻松合成说明了这一点。重要的是，我们提出了二铑（II）四天冬氨酸复合物的第一个晶体结构，它揭示了肽基配体的β-转角构象的保留；明显的氢键网络，以及导致铑中心不等价的近C 4对称性。该催化剂平台的实用性通过苄基 C(sp 3 )–H 键的对映选择性胺化得以体现，即使对于存在挑战的底物，也可以获得高达 95.5:4.5 er 的最先进水平的对映选择性与先前报道的催化剂系统。此外，我们发现这些配合物通过插入到酰胺氮的 C(sp
• Anthranilimide-based glycogen phosphorylase inhibitors for the treatment of type 2 diabetes: 1. Identification of 1-amino-1-cycloalkyl carboxylic acid headgroups
  作者：Steven M. Sparks、Pierette Banker、David M. Bickett、H. Luke Carter、Daphne C. Clancy、Scott H. Dickerson、Kate A. Dwornik、Dulce M. Garrido、Pamela L. Golden、Robert T. Nolte、Andrew J. Peat、Lauren R. Sheckler、Francis X. Tavares、Stephen A. Thomson、Liping Wang、James E. Weiel

  DOI：10.1016/j.bmcl.2008.11.085

  日期：2009.2

  Optimization of the amino acid residue within a series of anthranilimide-based glycogen phosphorylase inhibitors is described. These studies culminated in the identification of anthranilimides 16 and 22 which displayed potent in vitro inhibition of GPa in addition to reduced inhibition of CYP2C9 and excellent pharmacokinetic properties. (C) 2008 Elsevier Ltd. All rights reserved.
• Aza-Diels−Alder Reaction of Methyl 2-[(<i>R</i>)-1-Phenylethyl]iminoethanoate with Cyclopentadiene Using Practical and Environmentally Friendly Biphasic Solvent System
  作者：Norio Hashimoto、Hironobu Yasuda、Masaru Hayashi、Yoo Tanabe

  DOI：10.1021/op049828m

  日期：2005.1.1

  Aza-Diels-Aider reaction between 2-[(R)-1-phenylethyl]imino-ethanoate (1) and cyclopentadiene using the biphasic solvent system (TMSCI-CH3OH/toluene) gave (1S,3S,4R)-2[(R)-1-phenylethyl]-2-aza-bicyclo[2.2.1]hept-5-ene-3-carboxylates (3a) in 32% isolated yield. The present method is advantageous for the large-scale synthesis, because (i) the reported methods required harmful and expensive fluorinated chemicals, (ii) methyl analogue 3a was practically isolated as a crystalline solid, and (iii) the reaction was conducted with very little observable exotherm. In addition, the absolute configurations of the other three diastereomers 2, 4, and 5 were unambiguously determined.