(R)-(5-methyl-furan-2-yl)hydroxyacetic acid butyl ester | 649757-24-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (R)-(5-methyl-furan-2-yl)hydroxyacetic acid butyl ester
• 英文别名: butyl (2R)-2-hydroxy-2-(5-methylfuran-2-yl)acetate
• CAS: 649757-24-4
• 化学式: C₁₁H₁₆O₄
• 分子量: 212.246
• InChiKey: IPBDESKXJRNFFB-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(5-methyl-furan-2-yl)hydroxyacetic acid butyl ester 在 lithium aluminium tetrahydride 作用下， 生成 (S)-1-(5-methyl-2-furyl)ethane-1,2-diol
  参考文献：
  名称：

  Highly Enantioselective Synthesis of 2-Furanyl-hydroxyacetates from Furans via the Friedel−Crafts Reaction

  摘要：

  The Friedel-Crafts reaction of alkyl glyoxylates with variously substituted furans was found to be efficiently catalyzed under simple, undemanding conditions by a 6,6'-dibromo-BINOL/Ti(IV) complex with high enantioselectivity. The reaction afforded chiral substituted 2-furanyl-hydroxyacetic acid esters, compounds of high synthetic interest, in good yield and enantiomeric excess, in most examples in the range of 90-97%.

  DOI：

  10.1021/ol800927w
• 作为产物：
  描述：

  2-甲基呋喃 、 乙醛酸正丁酯 在 titanium(IV) isopropylate 、 (R)-6,6'-dibromo-1,1'-binaphth-2-ol 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以95%的产率得到(R)-(5-methyl-furan-2-yl)hydroxyacetic acid butyl ester
  参考文献：
  名称：

  Highly Enantioselective Synthesis of 2-Furanyl-hydroxyacetates from Furans via the Friedel−Crafts Reaction

  摘要：

  The Friedel-Crafts reaction of alkyl glyoxylates with variously substituted furans was found to be efficiently catalyzed under simple, undemanding conditions by a 6,6'-dibromo-BINOL/Ti(IV) complex with high enantioselectivity. The reaction afforded chiral substituted 2-furanyl-hydroxyacetic acid esters, compounds of high synthetic interest, in good yield and enantiomeric excess, in most examples in the range of 90-97%.

  DOI：

  10.1021/ol800927w

文献信息

• (Salen)Co(II) complex—an efficient catalyst for the high-pressure Friedel–Crafts reaction of 2-methylfuran with alkyl glyoxylates
  作者：Piotr Kwiatkowski、Elżbieta Wojaczyńska、Janusz Jurczak

  DOI：10.1016/j.tetasy.2003.08.012

  日期：2003.11

  The high-pressure (10 kbar) reaction of 2-methylfuran I with alkyl glyoxylates 2, catalyzed by the chiral (Salen)Co(II) complex 4, afforded the Friedel-Crafts products 3 both in good yield (up to 70%) and enantio selectivity (up to 76% ee). (C) 2003 Elsevier Ltd. All rights reserved.
• Highly Enantioselective Synthesis of 2-Furanyl-hydroxyacetates from Furans via the Friedel−Crafts Reaction
  作者：Jakub Majer、Piotr Kwiatkowski、Janusz Jurczak

  DOI：10.1021/ol800927w

  日期：2008.7.17

  The Friedel-Crafts reaction of alkyl glyoxylates with variously substituted furans was found to be efficiently catalyzed under simple, undemanding conditions by a 6,6'-dibromo-BINOL/Ti(IV) complex with high enantioselectivity. The reaction afforded chiral substituted 2-furanyl-hydroxyacetic acid esters, compounds of high synthetic interest, in good yield and enantiomeric excess, in most examples in the range of 90-97%.