<(3R)-(-)-3-<2-(pyridin-4-yl)ethyl>-2-oxopiperidin-1-yl>acetic acid | 172649-75-1

• 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: <(3R)-(-)-3-<2-(pyridin-4-yl)ethyl>-2-oxopiperidin-1-yl>acetic acid
• 英文别名: 2-Oxo-3-(2-(4-pyridinyl)ethyl)-1-piperidineacetic acid, (3R)-；2-[(3R)-2-oxo-3-(2-pyridin-4-ylethyl)piperidin-1-yl]acetic acid
• CAS: 172649-75-1
• 化学式: C₁₄H₁₈N₂O₃
• 分子量: 262.309
• InChiKey: XDJQLJZNNOKIIU-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  70.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  quinidinium <(3R)-(-)-3-<2-(pyridin-4-yl)ethyl>-2-oxopiperidin-1-yl>acetate 在 sodium hydroxide 作用下， 以 吡啶 为溶剂， 生成 <(3R)-(-)-3-<2-(pyridin-4-yl)ethyl>-2-oxopiperidin-1-yl>acetic acid
  参考文献：
  名称：

  A Highly Efficient Synthesis of Fibrinogen Receptor Antagonist L-734,217 via a Novel Chemoselective Silyl-Mediated Conjugate Addition of δ-Lactams to 4-Vinylpyridine

  摘要：

  A highly practical chromatography-free six-step synthesis of L-734,217 suitable for large scale preparation is described. The key chiral pyridine acid intermediate (R)-1 was prepared in four steps based on a novel chemoselective silyl-mediated conjugate addition of ethyl (2-oxopiperidin-1-yl)acetate to 4-vinylpyridine and a highly productive, recyclable, kinetic resolution with quinine. Subsequent salt breaking/peptide coupling with benzyl 3-(R)-aminobutyrate (2) in a biphasic system, followed by concomitant hydrogenation of the pyridine ring and debenzylation afforded L-734,217 in 20% overall yield (30% with one recyle) from 2-piperidone. The mechanism of this key conjugate addition to 4-vinylpyridine was studied by C-13 NMR.

  DOI：

  10.1021/jo951214f

文献信息

• FIBRINOGEN RECEPTOR ANTAGONISTS
  申请人：MERCK & CO., INC.

  公开号：EP0866705A1

  公开（公告）日：1998-09-30
• EP0866705A4
  申请人：——

  公开号：EP0866705A4

  公开（公告）日：1999-03-03
• [EN] FIBRINOGEN RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DU RECEPTEUR DE FIBRINOGENE
  申请人：MERCK & CO., INC.

  公开号：WO1997014417A1

  公开（公告）日：1997-04-24

  (EN) Fibrinogen receptor antagonists having structure, for example, of (I) or for example (II).(FR) Antagonistes du récepteur de fibrinogène présentant, par exemple, la structure de la formule (I), ou par exemple de la formule (II).