ethyl 3-formyl-4-[(2R,4S,5R)-5-hydroxy-2-phenyl-1,3-dioxan-4-yl]-1H-pyrrole-2-carboxylate | 1096364-72-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 3-formyl-4-[(2R,4S,5R)-5-hydroxy-2-phenyl-1,3-dioxan-4-yl]-1H-pyrrole-2-carboxylate
• CAS: 1096364-72-5
• 化学式: C₁₈H₁₉NO₆
• 分子量: 345.352
• InChiKey: FAHHYEMHAGSLQE-UWWQBHOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  97.8
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl (2R,4aR,6S,9bS)-6-methoxy-2-phenyl-4a,6,8,9b-tetrahydro-4H-[1,3]dioxino[4',5':5,6]pyrano[3,4-c]pyrrole-7-carboxylate 在 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以73%的产率得到ethyl 3-formyl-4-[(2R,4S,5R)-5-hydroxy-2-phenyl-1,3-dioxan-4-yl]-1H-pyrrole-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.