(S)-hydroxy-(4,5-dimethyl-furan-2-yl)-acetic acid (1'R,2'S,5'R)-8'-phenylmenthyl ester | 916067-33-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S)-hydroxy-(4,5-dimethyl-furan-2-yl)-acetic acid (1'R,2'S,5'R)-8'-phenylmenthyl ester
• 英文别名: [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] (2S)-2-(4,5-dimethylfuran-2-yl)-2-hydroxyacetate
• CAS: 916067-33-9
• 化学式: C₂₄H₃₂O₄
• 分子量: 384.516
• InChiKey: BUVURKGJMVATJS-XVJMICLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  (S)-hydroxy-(4,5-dimethyl-furan-2-yl)-acetic acid (1'R,2'S,5'R)-8'-phenylmenthyl ester 在 lithium aluminium tetrahydride 作用下， 生成 (R)-1-(4,5-dimethyl-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：

  di<(1R,2S,5R)-8-phenylmenthyl> fumarate 在 臭氧 、 magnesium bromide 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 (S)-hydroxy-(4,5-dimethyl-furan-2-yl)-acetic acid (1'R,2'S,5'R)-8'-phenylmenthyl ester
  参考文献：
  名称：

  Highly Diastereoselective Friedel−Crafts Reaction of Furans with 8-Phenylmenthyl Glyoxylate

  摘要：

  The Friedel-Crafts reaction of (1R)-8-phenylmenthyl glyoxylate with variously substituted furans was found to be efficiently promoted by SnCl(4) or magnesium salts with high diastereoselectivities. MgBr(2) performs especially well under simple, undemanding conditions, giving both high yields and high diastereoselectivities (> 90%). The reaction afforded chiral substituted furan-2-yl-hydroxyacetic acid esters, compounds of potentially high synthetic interest.

  DOI：

  10.1021/ol061943p

文献信息

• 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%.
• Highly Diastereoselective Friedel−Crafts Reaction of Furans with 8-Phenylmenthyl Glyoxylate
  作者：Piotr Kwiatkowski、Jakub Majer、Wojciech Chaładaj、Janusz Jurczak

  DOI：10.1021/ol061943p

  日期：2006.10.1

  The Friedel-Crafts reaction of (1R)-8-phenylmenthyl glyoxylate with variously substituted furans was found to be efficiently promoted by SnCl(4) or magnesium salts with high diastereoselectivities. MgBr(2) performs especially well under simple, undemanding conditions, giving both high yields and high diastereoselectivities (> 90%). The reaction afforded chiral substituted furan-2-yl-hydroxyacetic acid esters, compounds of potentially high synthetic interest.