(S)-2-(2-methoxy-2-methyl-[1,3]dioxolane-4-ylmethyl)-isoindole-1,3-dione | 879507-95-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (S)-2-(2-methoxy-2-methyl-[1,3]dioxolane-4-ylmethyl)-isoindole-1,3-dione
• 英文别名: 2-[[(4S)-2-methoxy-2-methyl-1,3-dioxolan-4-yl]methyl]isoindole-1,3-dione
• CAS: 879507-95-6
• 化学式: C₁₄H₁₅NO₅
• 分子量: 277.277
• InChiKey: TYMPSRQANLLUJX-CUVJYRNJSA-N

物化性质

• 沸点：
  391.1±37.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-(2-methoxy-2-methyl-[1,3]dioxolane-4-ylmethyl)-isoindole-1,3-dione 在 三甲基氯硅烷 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 38.0h， 生成
  参考文献：
  名称：

  Pilot Scale Process Development of SL65.0102-10, an N-Diazabicyclo[2.2.2]-octylmethyl Benzamide

  摘要：

  The process development and improvements for route selection, adapted to large scale for the pilot-scale preparation of SL65.0102-10, an N-diazabicyclo[2.2.2]-octylmethyl benzamide, a 5-HT3 and 5-HT4 receptor active ligand for the treatment of neurological disorders such as cognition impairment, are described in this article. Notable steps and enhancements are compared to the original route, including the improvement of a chiral epoxide synthesis by shortening the number of chemical steps, the deprotection of a quaternary ammonium salt, and the redesign of the final amidification coupling to avoid chromatography.

  DOI：

  10.1021/acs.oprd.6b00262
• 作为产物：
  描述：

  S-(-)-4-phthalimidomethyl-2,2-dimethyl-1,3-dioxolane 在 盐酸 、 4-甲基苯磺酸吡啶 作用下， 以 水 、 甲苯 为溶剂， 反应 2.25h， 生成 (S)-2-(2-methoxy-2-methyl-[1,3]dioxolane-4-ylmethyl)-isoindole-1,3-dione
  参考文献：
  名称：

  Pilot Scale Process Development of SL65.0102-10, an N-Diazabicyclo[2.2.2]-octylmethyl Benzamide

  摘要：

  The process development and improvements for route selection, adapted to large scale for the pilot-scale preparation of SL65.0102-10, an N-diazabicyclo[2.2.2]-octylmethyl benzamide, a 5-HT3 and 5-HT4 receptor active ligand for the treatment of neurological disorders such as cognition impairment, are described in this article. Notable steps and enhancements are compared to the original route, including the improvement of a chiral epoxide synthesis by shortening the number of chemical steps, the deprotection of a quaternary ammonium salt, and the redesign of the final amidification coupling to avoid chromatography.

  DOI：

  10.1021/acs.oprd.6b00262

文献信息

• [EN] PROCESS FOR PREPARATION OF PHTALIMIDE<br/>[FR] PROCESSUS DE PREPARATION DE PHTALIMIDE
  申请人：ASTRAZENECA AB

  公开号：WO2006031179A1

  公开（公告）日：2006-03-23

  The present invention is directed to a novel process for the synthesis of (S) -glycidyl phthalimide and to novel intermediates in the process. The process comprises, reacting a (R) -3 -Chloro-1,2-propanediol and phtalimide salt. Then reacting the product with trimethylorthoacetate and an essentially water free acid. Then reacting the product with acetyl halogenide and do a basic ester hydrolysis.

  本发明涉及一种合成(S)-甘氨酰噁二酰亚胺的新方法，以及该方法中的新中间体。该方法包括，将(R)-3-氯-1,2-丙二醇和邻苯二甲酰亚胺盐反应。然后将产物与三甲基正醛酸酯和基本无水酸反应。然后将产物与乙酰卤和进行碱性酯水解。
• [EN] PREPARATION METHOD FOR (S)-GLYCIDYL PHTHALIMIDE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE (S)-GLYCIDYLE PHTALIMIDE<br/>[ZH] 一种(S)-缩水甘油邻苯二甲酰亚胺的制备方法
  申请人：XIN FA PHARMACEUTICAL CO LTD

  公开号：WO2020051967A1

  公开（公告）日：2020-03-19

  本发明提供一种(S)-缩水甘油邻苯二甲酰亚胺(Ⅱ)的制备方法。利用邻苯二甲酰亚胺(Ⅲ)和(S)-1-取代基环氧丙烷(Ⅳ)为原料，在催化剂作用下反应生成2-((S)-3-取代基-2-羟基丙基)异二氢吲哚-1,3-二酮(Ⅴ)，最后经关环反应生成(S)-缩水甘油邻苯二甲酰亚胺(Ⅱ)。本发明方法原料廉价易得，反应条件易于实现，成本低；反应路线简短，操作简便，后处理简单；副反应少，目标产物收率和纯度高，适合工业化生产。