methyl 3-(1,3-dioxoisoindolin-2-yl)-2-oxopropanoate | 153646-24-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl 3-(1,3-dioxoisoindolin-2-yl)-2-oxopropanoate
• 英文别名: methyl N-phthaloyl-3-amino-2-oxopropanoate；methyl 3-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-2-oxopropanoate；methyl 3-(1,3-dioxoisoindol-2-yl)-2-oxopropanoate
• CAS: 153646-24-3
• 化学式: C₁₂H₉NO₅
• mdl: MFCD23144250
• 分子量: 247.207
• InChiKey: CRFRUUGFDCLUOV-UHFFFAOYSA-N

物化性质

• 沸点：
  392.5±25.0 °C(Predicted)
• 密度：
  1.422±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-(1,3-dioxoisoindolin-2-yl)-2-oxopropanoate 在 (benzene)>Cl 盐酸 、 tetrafluoroboric acid 、 氢气 作用下， 以 甲醇 为溶剂， 30.0~60.0 ℃ 、10.13 MPa 条件下， 反应 72.5h， 生成 (S)-3-(1,3-二氧代-1,3-二氢-异吲哚-2-基)-2-羟基-丙酸
  参考文献：
  名称：

  Enantioselective synthesis of L- and D-isoserine via asymmetric hydrogenation of methyl N-phthaloyl-3-amino-2-oxopropanoate

  摘要：

  L- and D-isoserine were synthesized enantioselectively via asymmetric hydrogenation of 3-amino-2-oxoester 5 catalyzed by [RuCl(binap)(benzene)]Cl. Recrystallization and deprotection of (S)-6 (81% ee) afforded enantiomerically pure L-isoserine. The enantioface selection by the catalyst was opposite to that observed in asymmetric hydrogenation of other 2-oxoesters, such as methyl phenylglyoxylate and methyl 2-oxocyclohexylacetate.

  DOI：

  10.1016/s0957-4166(00)80068-3
• 作为产物：
  描述：

  N-邻苯二甲酰甘氨酰氯 在 盐酸 、 sodium iodide 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 methyl 3-(1,3-dioxoisoindolin-2-yl)-2-oxopropanoate
  参考文献：
  名称：

  Enantioselective synthesis of L- and D-isoserine via asymmetric hydrogenation of methyl N-phthaloyl-3-amino-2-oxopropanoate

  摘要：

  L- and D-isoserine were synthesized enantioselectively via asymmetric hydrogenation of 3-amino-2-oxoester 5 catalyzed by [RuCl(binap)(benzene)]Cl. Recrystallization and deprotection of (S)-6 (81% ee) afforded enantiomerically pure L-isoserine. The enantioface selection by the catalyst was opposite to that observed in asymmetric hydrogenation of other 2-oxoesters, such as methyl phenylglyoxylate and methyl 2-oxocyclohexylacetate.

  DOI：

  10.1016/s0957-4166(00)80068-3

文献信息

• [EN] IMIDAZOTRIAZINONE COMPOUNDS<br/>[FR] COMPOSÉS IMIDAZOTRIAZINONES
  申请人：ENVIVO PHARMACEUTICALS INC

  公开号：WO2012040230A1

  公开（公告）日：2012-03-29

  The present invention provides imidazotriazinone compounds which are inhibitors of phosphodiesterase 9. The present invention further provides processes, pharmaceutical compositions, pharmaceutical preparations and pharmaceutical use of the compounds in the treatment of PDE9 associated diseases or disorders in mammals, including CNS or neurodegeneration disorder.

  本发明提供了嘧啶三唑酮类化合物，这些化合物是磷酸二酯酶9的抑制剂。本发明还提供了在治疗哺乳动物中PDE9相关疾病或紊乱，包括中枢神经系统或神经退行性疾病中使用这些化合物的方法、药物组合物、药物制剂和药物用途。
• [EN] IMIDAZOTRIAZINONE COMPOUNDS<br/>[FR] COMPOSÉS D'IMIDAZOTRIAZINONE
  申请人：ENVIVO PHARMACEUTICALS INC

  公开号：WO2013142269A1

  公开（公告）日：2013-09-26

  The present invention provides imidazotriazinone compounds which are inhibitors of phosphodiesterase 9 and pharmaceutically acceptable salt thereof. The present invention further provides processes, pharmaceutical compositions, pharmaceutical preparations and pharmaceutical use of the compounds in the treatment of PDE9 associated diseases or disorders in mammals, including humans.

  本发明提供了咪唑三唑酮化合物，它们是磷酸二酯酶9的抑制剂及其药用盐。本发明还提供了用于治疗哺乳动物，包括人类，PDE9相关疾病或疾病的过程、药物组成、药物制剂和化合物的药用。
• IMIDAZOTRIAZINONE COMPOUNDS
  申请人：Ripka Amy

  公开号：US20120157458A1

  公开（公告）日：2012-06-21

  The present invention provides imidazotriazinone compounds which are inhibitors of phosphodiesterase 9. The present invention further provides processes, pharmaceutical compositions, pharmaceutical preparations and pharmaceutical use of the compounds in the treatment of PDE9 associated diseases or disorders in mammals, including humans.

  本发明提供了咪唑三唑酮类化合物，这些化合物是磷酸二酯酶9的抑制剂。本发明还提供了制备这些化合物的方法、药物组成物、制药制剂以及在哺乳动物中（包括人类）治疗与PDE9相关的疾病或紊乱的药物用途。
• Imidazotriazinone Compounds
  申请人：FORUM Pharmaceuticals, Inc.

  公开号：US20150191476A1

  公开（公告）日：2015-07-09

  The present invention provides imidazotriazinone compounds which are inhibitors of phosphodiesterase 9 and pharmaceutically acceptable salt thereof. The present invention further provides processes, pharmaceutical compositions, pharmaceutical preparations and pharmaceutical use of the compounds in the treatment of PDE9 associated diseases or disorders in mammals, including humans.

  本发明提供了咪唑三嗪酮类化合物及其医药上可接受的盐，这些化合物是磷酸二酯酶9的抑制剂。本发明还提供了制备该化合物的方法、药物组合物、药物制剂以及在哺乳动物，包括人类中治疗PDE9相关疾病或疾病的药物用途。
• US9540380B2
  申请人：——

  公开号：US9540380B2

  公开（公告）日：2017-01-10