(-)-(3R,4R)-β-(3,4-dimethoxyphenyl)acrylic acid 4-hydroxy-4-methyl-5-oxotetrahydrofuran-3-yl ester | 893418-50-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (-)-(3R,4R)-β-(3,4-dimethoxyphenyl)acrylic acid 4-hydroxy-4-methyl-5-oxotetrahydrofuran-3-yl ester
• CAS: 893418-50-3
• 化学式: C₁₆H₁₈O₇
• 分子量: 322.315
• InChiKey: MPWZCCFEAVGZNL-MOCUHTECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.94
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  91.29
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (-)-(3R,4R)-β-(3,4-dimethoxyphenyl)acrylic acid 4-hydroxy-4-methyl-5-oxotetrahydrofuran-3-yl ester 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以64%的产率得到3-(3,4-dimethoxyphenyl)acrylic acid 4-methyl-5-oxo-2,5-dihydrofuran-3-yl ester
  参考文献：
  名称：

  An efficient Amano PS-catalyzed chemo-, regio- and enantioselective hydrolysis of (±)-2,3-di-O-acetyl-2-C-methyl-d-erythrono-1,4-lactone: a facile preparation of bioactive natural products (−)-saccharinic acid lactone and potassium (2R,3R)-2,3,4-trihydroxy-2-methylbutanoate

  摘要：

  Saccharinic acid lactone (-)-1a is a suitable building block for the synthesis of many bioactive natural products. Amano PS-induced chemo-, regio- and enantioselective hydrolysis of diacetyl lactone (+/-)-3 has been carried out to obtain (-)-1a in 46% yield with 99% ee and diacetyl lactone (+)-3 in 49% yield with 99% ee. The Amano PS-catalyzed enantioselective acylation of (+/-)-1a with vinyl acetate as an acyl donor was relatively less efficient and furnished (-)-7 in 31% yield with 99% ee and (+)-1a in 63% yield. The conversion of (-)-1a to leaf-closing substance 2a and an attempted approach to naturally occurring compounds 1b and 2b have been also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.02.025
• 作为产物：
  描述：

  (-)-(3R,4R)-acetic acid 4-hydroxy-4-methyl-5-oxotetrahydrofuran-3-yl ester 在 4-二甲氨基吡啶 、 potassium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (-)-(3R,4R)-β-(3,4-dimethoxyphenyl)acrylic acid 4-hydroxy-4-methyl-5-oxotetrahydrofuran-3-yl ester
  参考文献：
  名称：

  An efficient Amano PS-catalyzed chemo-, regio- and enantioselective hydrolysis of (±)-2,3-di-O-acetyl-2-C-methyl-d-erythrono-1,4-lactone: a facile preparation of bioactive natural products (−)-saccharinic acid lactone and potassium (2R,3R)-2,3,4-trihydroxy-2-methylbutanoate

  摘要：

  Saccharinic acid lactone (-)-1a is a suitable building block for the synthesis of many bioactive natural products. Amano PS-induced chemo-, regio- and enantioselective hydrolysis of diacetyl lactone (+/-)-3 has been carried out to obtain (-)-1a in 46% yield with 99% ee and diacetyl lactone (+)-3 in 49% yield with 99% ee. The Amano PS-catalyzed enantioselective acylation of (+/-)-1a with vinyl acetate as an acyl donor was relatively less efficient and furnished (-)-7 in 31% yield with 99% ee and (+)-1a in 63% yield. The conversion of (-)-1a to leaf-closing substance 2a and an attempted approach to naturally occurring compounds 1b and 2b have been also described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.02.025