(3aR,7aS)-5-benzyl-2,2-dimethyltetrahydro[1,3]dioxolo[4,5-c]pyridin-7(4H)-one | 476310-40-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3aR,7aS)-5-benzyl-2,2-dimethyltetrahydro[1,3]dioxolo[4,5-c]pyridin-7(4H)-one
• 英文别名: (3aR,7aS)-5-benzyl-2,2-dimethyl-3a,4,6,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyridin-7-one
• CAS: 476310-40-4
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: QLIMXUVKIKLXLV-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,7aS)-5-benzyl-2,2-dimethyltetrahydro[1,3]dioxolo[4,5-c]pyridin-7(4H)-one 在 sodium tetrahydroborate 、 sodium chloride 作用下， 以 甲醇 为溶剂， 反应 64.0h， 以85%的产率得到(3aR,7aR)-5-benzyl-2,2-dimethylhexahydro[1,3]dioxolo[4,5-c]pyridin-7-ol
  参考文献：
  名称：

  Design and Development of a Common Synthetic Strategy for a Variety of 1-N-Iminosugars

  摘要：

  [GRAPHICS]A new synthetic strategy has been developed for a general approach toward the synthesis of a variety of 1-N-iminosugar-type glycosidase inhibitors utilizing precursors developed by the PET-mediated cyclization of alpha-trimethylsilylmethylamine radical cation to a tethered pi-functionality.

  DOI：

  10.1021/ol026711e
• 作为产物：
  描述：

  (3aR,7aR)-5-benzyl-2,2-dimethyl-7-methylenehexahydro-[1,3]dioxolo[4,5-c]pyridine 在 吡啶 、 sodium periodate 、 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 25.0h， 生成 (3aR,7aS)-5-benzyl-2,2-dimethyltetrahydro[1,3]dioxolo[4,5-c]pyridin-7(4H)-one
  参考文献：
  名称：

  A new access to polyhydroxy piperidines of the azasugar class: synthesis and glycosidase inhibition studies

  摘要：

  一种新的合成策略被设计用于获得属于糖氨基酸酶抑制剂类的多羟基化哌啶的多样性。关键前驱体 (3aR, 7aR)-5-苄基-2,2-二甲基-7-亚烯基六氢[1,3]二氧杂[4,5-c]吡啶是通过光诱导电子转移（PET）环化反应获得的，该反应涉及相应的α-三甲基硅基甲基氨基自由基阳离子与连接的炔烃功能团。新分子的抑制特性已被评估，结果发现它们对某些β-糖苷酶的抑制作用为中等到弱。

  DOI：

  10.1039/b307455b

文献信息

• A new access to polyhydroxy piperidines of the azasugar class: synthesis and glycosidase inhibition studies
  作者：Ganesh Pandey、Manmohan Kapur、M. Islam Khan、Sushama M. Gaikwad

  DOI：10.1039/b307455b

  日期：——

  A new synthetic strategy has been devised to access a variety of polyhydroxylated piperidines belonging to the azasugar class of glycosidase inhibitors. The key precursor (3aR, 7aR)-5-benzyl-2,2-dimethyl-7-methylenehexahydro[1,3]dioxo[4,5-c]pyridine is obtained by photoinduced electron transfer (PET) cyclization of the corresponding α-trimethylsilylmethylamine radical cation to the tethered acetylene functionality. The new molecules have been evaluated for inhibitory properties for certain β-glycosidases and have been found to be moderate to weak inhibitors of the enzymes under study.

  一种新的合成策略被设计用于获得属于糖氨基酸酶抑制剂类的多羟基化哌啶的多样性。关键前驱体 (3aR, 7aR)-5-苄基-2,2-二甲基-7-亚烯基六氢[1,3]二氧杂[4,5-c]吡啶是通过光诱导电子转移（PET）环化反应获得的，该反应涉及相应的α-三甲基硅基甲基氨基自由基阳离子与连接的炔烃功能团。新分子的抑制特性已被评估，结果发现它们对某些β-糖苷酶的抑制作用为中等到弱。
• Design and Development of a Common Synthetic Strategy for a Variety of 1-<i>N</i>-Iminosugars
  作者：Ganesh Pandey、Manmohan Kapur

  DOI：10.1021/ol026711e

  日期：2002.10.1

  [GRAPHICS]A new synthetic strategy has been developed for a general approach toward the synthesis of a variety of 1-N-iminosugar-type glycosidase inhibitors utilizing precursors developed by the PET-mediated cyclization of alpha-trimethylsilylmethylamine radical cation to a tethered pi-functionality.