diethyl 3,3.-[(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]bis(1Hpyrrole-2-carboxylate) | 1096364-71-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: diethyl 3,3.-[(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]bis(1Hpyrrole-2-carboxylate)
• 英文别名: ethyl 3-[(4R,5R)-5-(2-ethoxycarbonyl-1H-pyrrol-3-yl)-2,2-dimethyl-1,3-dioxolan-4-yl]-1H-pyrrole-2-carboxylate
• CAS: 1096364-71-4
• 化学式: C₁₉H₂₄N₂O₆
• 分子量: 376.409
• InChiKey: NNTSMVNKCWPKGA-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (4R,5R)-2,2-dimethyl-4,5-bis[(E)-2-(p-tolylsulfonyl)ethenyl]-1,3-dioxolane 、 异氰基乙酸乙酯 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以92%的产率得到diethyl 3,3.-[(4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]bis(1Hpyrrole-2-carboxylate)
  参考文献：
  名称：

  Densely Functionalized Chiral Pyrroles from Endocyclic, Exocyclic, and Acyclic Vinyl Sulfone-Modified Carbohydrates

  摘要：

  A wide range of vinyl sulfone-modified carbohydrates have been prepared as starting materials for the synthesis of polysubstituted chiral pyrroles. All these vinyl sulfones reacted efficiently with ethylisocyanoacetate to generate a plethora of new pyrrole derivatives. Furanosyl rings opened up during pyrrole synthesis, and pyranosyl rings were opened up by reacting the pyrrole with POCl3/DMF. This paper also reports one of the most efficient and practical routes for the synthesis of beta-substituted pyrroles.

  DOI：

  10.1021/jo801948m

文献信息

• Densely Functionalized Chiral Pyrroles from Endocyclic, Exocyclic, and Acyclic Vinyl Sulfone-Modified Carbohydrates
  作者：Rahul Bhattacharya、Ananta Kumar Atta、Debanjana Dey、Tanmaya Pathak

  DOI：10.1021/jo801948m

  日期：2009.1.16

  A wide range of vinyl sulfone-modified carbohydrates have been prepared as starting materials for the synthesis of polysubstituted chiral pyrroles. All these vinyl sulfones reacted efficiently with ethylisocyanoacetate to generate a plethora of new pyrrole derivatives. Furanosyl rings opened up during pyrrole synthesis, and pyranosyl rings were opened up by reacting the pyrrole with POCl3/DMF. This paper also reports one of the most efficient and practical routes for the synthesis of beta-substituted pyrroles.