(2R,3R)-2-(4-Methoxy-phenyl)-5-methyl-2,3-dihydro-furan-3,4-dicarboxylic acid 4-isopropyl ester 3-methyl ester | 326487-47-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,3R)-2-(4-Methoxy-phenyl)-5-methyl-2,3-dihydro-furan-3,4-dicarboxylic acid 4-isopropyl ester 3-methyl ester
• 英文别名: 3-O-methyl 4-O-propan-2-yl (2R,3R)-2-(4-methoxyphenyl)-5-methyl-2,3-dihydrofuran-3,4-dicarboxylate
• CAS: 326487-47-2
• 化学式: C₁₈H₂₂O₆
• 分子量: 334.369
• InChiKey: CXMVBBLZKMFEOG-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-(4-Methoxy-phenyl)-5-methyl-2,3-dihydro-furan-3,4-dicarboxylic acid 4-isopropyl ester 3-methyl ester 在 lithium hydroxide 、 氯化亚砜 、 三乙胺 作用下， 以 甲醇 、 水 、 苯 为溶剂， 反应 12.75h， 生成 propan-2-yl (2R,3R)-3-[(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl]-2-(4-methoxyphenyl)-5-methyl-2,3-dihydrofuran-4-carboxylate
  参考文献：
  名称：

  Asymmetric Mn(III)-based radical synthesis of functionalized 2,3-dihydrofurans

  摘要：

  The oxidative radical addition of alkyl acetoacetates to p-methoxycinnamoyl oxazolidinones promoted by Mn(III) has been studied. It only gives trans-disubstituted 2,3-dihydrofurans, with d.r. ranging from 2:1 to 9:1, depending on the substituent of the chiral auxiliary. After chromatographic separation of the two diastereomers, the oxazolidinone can be removed to afford enantiopure dihydrofuranyl esters in good overall yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01729-9
• 作为产物：
  描述：

  乙酰乙酸异丙酯 在 manganese triacetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 溶剂黄146 为溶剂， 反应 5.5h， 生成 (2R,3R)-2-(4-Methoxy-phenyl)-5-methyl-2,3-dihydro-furan-3,4-dicarboxylic acid 4-isopropyl ester 3-methyl ester
  参考文献：
  名称：

  Asymmetric Mn(III)-based radical synthesis of functionalized 2,3-dihydrofurans

  摘要：

  The oxidative radical addition of alkyl acetoacetates to p-methoxycinnamoyl oxazolidinones promoted by Mn(III) has been studied. It only gives trans-disubstituted 2,3-dihydrofurans, with d.r. ranging from 2:1 to 9:1, depending on the substituent of the chiral auxiliary. After chromatographic separation of the two diastereomers, the oxazolidinone can be removed to afford enantiopure dihydrofuranyl esters in good overall yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01729-9

文献信息

• Asymmetric Mn(III)-based radical synthesis of functionalized 2,3-dihydrofurans
  作者：Frédéric Garzino、Alain Méou、Pierre Brun

  DOI：10.1016/s0040-4039(00)01729-9

  日期：2000.12

  The oxidative radical addition of alkyl acetoacetates to p-methoxycinnamoyl oxazolidinones promoted by Mn(III) has been studied. It only gives trans-disubstituted 2,3-dihydrofurans, with d.r. ranging from 2:1 to 9:1, depending on the substituent of the chiral auxiliary. After chromatographic separation of the two diastereomers, the oxazolidinone can be removed to afford enantiopure dihydrofuranyl esters in good overall yield. (C) 2000 Elsevier Science Ltd. All rights reserved.