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 | 1096364-59-8

• 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 (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
• 英文别名: ethyl (1S,7S,9R,12R)-7-methoxy-12-phenyl-8,11,13-trioxa-4-azatricyclo[7.4.0.02,6]trideca-2,5-diene-5-carboxylate
• CAS: 1096364-59-8
• 化学式: C₁₉H₂₁NO₆
• 分子量: 359.379
• InChiKey: OMJKTGHJELZKPV-HQJJXPTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  79
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (2R,4aR,6S,8aR)-6-methoxy-2-phenyl-8-tosyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine 、 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76%的产率得到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
  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.