2-(5-(4-methoxybenzyl)-6-oxo-2-oxa-5-azaspiro[3.5]nonan-9-yl)isoindoline-1,3-dione | 1449603-86-4

• 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: 2-(5-(4-methoxybenzyl)-6-oxo-2-oxa-5-azaspiro[3.5]nonan-9-yl)isoindoline-1,3-dione
• CAS: 1449603-86-4
• 化学式: C₂₃H₂₂N₂O₅
• 分子量: 406.438
• InChiKey: IALFGTLLNFMSNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  76.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(5-(4-methoxybenzyl)-6-oxo-2-oxa-5-azaspiro[3.5]nonan-9-yl)isoindoline-1,3-dione 在 ammonium cerium (IV) nitrate 、 水 作用下， 以 乙腈 为溶剂， 反应 2.25h， 以54%的产率得到2-(6-oxo-2-oxa-5-azaspiro[3.5]nonan-9-yl)isoindoline-1,3-dione
  参考文献：
  名称：

  Synthesis and Stability of Oxetane Analogs of Thalidomide and Lenalidomide

  摘要：

  Oxetanes are used in drug discovery to enable physicochemical and metabolic property enhancement for the structures to which they are grafted. An imide C=O to oxetane swap on thalidomide and lenalidomide templates provides analogs with similar physicochemical and in vitro properties of the parent drugs, with an important exception: oxetane analog 2 displays a clear differentiation with respect to human plasma stability. The prospect of limiting in vivo stability/metabolism, blocking in vivo racemization, and potentially altering teratogenicity is appealing.

  DOI：

  10.1021/ol401705a
• 作为产物：
  描述：

  C₂₃H₂₃ClN₂O₅ 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以700 mg的产率得到2-(5-(4-methoxybenzyl)-6-oxo-2-oxa-5-azaspiro[3.5]nonan-9-yl)isoindoline-1,3-dione
  参考文献：
  名称：

  Synthesis and Stability of Oxetane Analogs of Thalidomide and Lenalidomide

  摘要：

  Oxetanes are used in drug discovery to enable physicochemical and metabolic property enhancement for the structures to which they are grafted. An imide C=O to oxetane swap on thalidomide and lenalidomide templates provides analogs with similar physicochemical and in vitro properties of the parent drugs, with an important exception: oxetane analog 2 displays a clear differentiation with respect to human plasma stability. The prospect of limiting in vivo stability/metabolism, blocking in vivo racemization, and potentially altering teratogenicity is appealing.

  DOI：

  10.1021/ol401705a