(S)-3-amino-1-(p-methoxybenzyl)-4,4-dimethylpyrrolidin-2-one | 1248826-58-5

• 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: (S)-3-amino-1-(p-methoxybenzyl)-4,4-dimethylpyrrolidin-2-one
• 英文别名: (3S)-3-amino-1-[(4-methoxyphenyl)methyl]-4,4-dimethylpyrrolidin-2-one
• CAS: 1248826-58-5
• 化学式: C₁₄H₂₀N₂O₂
• 分子量: 248.325
• InChiKey: YFFGNQWRZNEDPG-GFCCVEGCSA-N

物化性质

• 沸点：
  415.2±45.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-amino-1-(p-methoxybenzyl)-4,4-dimethylpyrrolidin-2-one 在 ammonium cerium (IV) nitrate 、 5% Pd(II)/C(eggshell) 、 氢气 作用下， 以 水 、 乙腈 、 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 20.0h， 以67%的产率得到(S)-3-amino-4,4-dimethylpyrrolidin-2-one
  参考文献：
  名称：

  Straightforward preparation of enantiopure 3-amino-4,4-dimethylpyrrolidin-2-one and its derivatives

  摘要：

  An easy access to both enantiomers of 3-amino- and 3-(dimethylamino)-4,4-dimethylpyrrolidin-2-one from rac-pantolactam using (R)-alpha-methylbenzylamine as a chiral auxiliary is described. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.06.028
• 作为产物：
  描述：

  (3S,1'R)-1-(p-methoxybenzyl)-4,4-dimethyl-3-[(1-phenylethyl)amino]pyrrolidin-2-one 在 盐酸 、 5% Pd(II)/C(eggshell) 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 67.0h， 以94%的产率得到(S)-3-amino-1-(p-methoxybenzyl)-4,4-dimethylpyrrolidin-2-one
  参考文献：
  名称：

  Straightforward preparation of enantiopure 3-amino-4,4-dimethylpyrrolidin-2-one and its derivatives

  摘要：

  An easy access to both enantiomers of 3-amino- and 3-(dimethylamino)-4,4-dimethylpyrrolidin-2-one from rac-pantolactam using (R)-alpha-methylbenzylamine as a chiral auxiliary is described. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.06.028

文献信息

• Chemical compounds as H—PGDS inhibitors
  申请人：GlaxoSmithKline Intellectual Property Development Limited

  公开号：US11149035B2

  公开（公告）日：2021-10-19

  A compound of formula (I) wherein R1, R2, R3, R4, X, Y, and A are as defined herein. The compounds of the present invention are inhibitors of hematopoletic prostaglandin D synthase (H-PGDS) and can be useful in the treatment of Duchenne muscular dystrophy. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting H-PGDS activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

  式 (I) 的化合物 其中 R1、R2、R3、R4、X、Y 和 A 如本文所定义。 本发明的化合物是血液前列腺素 D 合酶（H-PGDS）的抑制剂，可用于治疗杜氏肌营养不良症。因此，本发明进一步涉及包含本发明化合物的药物组合物。本发明还进一步涉及使用本发明化合物或包含本发明化合物的药物组合物抑制 H-PGDS 活性和治疗与之相关疾病的方法。
• Chemical Compounds as H-PGDS Inhibitors
  申请人：GlaxoSmithKline Intellectual Property Development Limited

  公开号：US20200123152A1

  公开（公告）日：2020-04-23

  A compound of formula (I) wherein R 1 , R 2 , R 3 , R 4 , X, Y, and A are as defined herein. The compounds of the present invention are inhibitors of hematopoletic prostaglandin D synthase (H-PGDS) and can be useful in the treatment of Duchenne muscular dystrophy. Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting H-PGDS activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.
• Straightforward preparation of enantiopure 3-amino-4,4-dimethylpyrrolidin-2-one and its derivatives
  作者：Pelayo Camps、Diego Muñoz-Torrero、Jordi Rull、José Antonio Mayoral、Teresa Calvet、Mercè Font-Bardia

  DOI：10.1016/j.tetasy.2010.06.028

  日期：2010.9

  An easy access to both enantiomers of 3-amino- and 3-(dimethylamino)-4,4-dimethylpyrrolidin-2-one from rac-pantolactam using (R)-alpha-methylbenzylamine as a chiral auxiliary is described. (C) 2010 Elsevier Ltd. All rights reserved.