2-oxo-2,5-dihydro-furan-3-carboxylic acid methyl ester | 63731-11-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 2-oxo-2,5-dihydro-furan-3-carboxylic acid methyl ester
• 英文别名: Methyl 2-oxo-2,5-dihydrofuran-3-carboxylate；methyl 5-oxo-2H-furan-4-carboxylate
• CAS: 63731-11-3
• 化学式: C₆H₆O₄
• 分子量: 142.111
• InChiKey: BGXMKPPPBMSLNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-oxotetrahydrofuran-3-carboxylic acid methyl ester 在 吡啶 、 苯基氯化硒 、 双氧水 作用下， 生成 2-oxo-2,5-dihydro-furan-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Enantioselective conjugate additions of silylketene acetals to 2-carboxycyclopentenones promoted by chiral Ti complexes

  摘要：

  The conjugate addition of silylketeneacetals to 2-carbalkoxycyclopentenones 1 promoted by TADDOL . TiCl2 complexes was studied. The reactions are highly syn selective. The enantioselectivity depends on the size of the substrate ester group, with the methyl ester 1b being more enantioselective than the ethyl ester 1a. E.c. up to 47% are achieved. The absolute configuration of the major product was established by chemical correlation to the known (+)-isodchydroiridodiol. The reaction of representative doubly activated alkenes was studied: good results were obtained with cyclopentenones and gamma-butenolides. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00825-9

文献信息

• QUESADA M. L.; SCHLESSINGER R. H., J. ORG. CHEM. <JOCE-AH>, 1978, 43, NO 2, 346-347
  作者：QUESADA M. L.、 SCHLESSINGER R. H.

  DOI：——

  日期：——
• Enantioselective conjugate additions of silylketene acetals to 2-carboxycyclopentenones promoted by chiral Ti complexes
  作者：Anna Bernardi、Katia Karamfilova、Silvia Sanguinetti、Carlo Scolastico

  DOI：10.1016/s0040-4020(97)00825-9

  日期：1997.9

  The conjugate addition of silylketeneacetals to 2-carbalkoxycyclopentenones 1 promoted by TADDOL . TiCl2 complexes was studied. The reactions are highly syn selective. The enantioselectivity depends on the size of the substrate ester group, with the methyl ester 1b being more enantioselective than the ethyl ester 1a. E.c. up to 47% are achieved. The absolute configuration of the major product was established by chemical correlation to the known (+)-isodchydroiridodiol. The reaction of representative doubly activated alkenes was studied: good results were obtained with cyclopentenones and gamma-butenolides. (C) 1997 Published by Elsevier Science Ltd.