3-((S)-5-Oxo-2,5-dihydro-furan-2-yl)-propionic acid isopropyl ester | 200408-64-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-((S)-5-Oxo-2,5-dihydro-furan-2-yl)-propionic acid isopropyl ester
• CAS: 200408-64-6
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: PWAKUMNSIBRQOE-QMMMGPOBSA-N

物化性质

• 沸点：
  317.9±15.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-((S)-5-Oxo-2,5-dihydro-furan-2-yl)-propionic acid isopropyl ester 在 4-二甲氨基吡啶 、 正丁基锂 、 二异丁基氢化铝 、 三乙胺 作用下， 以 正己烷 、 甲苯 、 乙腈 为溶剂， 生成 (Z)-(S)-1,7-Bis-(tert-butyl-diphenyl-silanyloxy)-hept-2-en-4-ol
  参考文献：
  名称：

  A new methodology for the stereoselective synthesis of 4-substituted butenolides: Asymmetric Michael addition reaction of 2-(trimethylsilyloxy)furans to oxazolidinone enoates

  摘要：

  Chiral Lewis acid promoted Michael addition of 2-(trimethylsilyloxy)furans to oxazolidinone enoates (2) in the presence of hexafluoroisopropanol proceeded stereoselectively to give 4-substituted butenolides in good yields. A 1:1 complex prepared in situ from Sc(OTf)(3) and 3,3'-bis(diethylaminomethyl)-1,1'-bi-2-naphthol 5b showed excellent anti-selectivity and moderate enantioselectivity, while Cu(OTf)(2)-bis(oxazoline) complex exhibited excellent enantioselectivity and moderate to good anti-selectivity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10152-1
• 作为产物：
  描述：

  titanium(IV)isopropoxide 、 (S)-3-[3-(2',5'-dihydro-5'-oxo-2'-furyl)]propanoyl-1,3-oxazolidin-2-one 以 异丙醇 为溶剂， 反应 7.0h， 以89%的产率得到3-((S)-5-Oxo-2,5-dihydro-furan-2-yl)-propionic acid isopropyl ester
  参考文献：
  名称：

  A new methodology for the stereoselective synthesis of 4-substituted butenolides: Asymmetric Michael addition reaction of 2-(trimethylsilyloxy)furans to oxazolidinone enoates

  摘要：

  Chiral Lewis acid promoted Michael addition of 2-(trimethylsilyloxy)furans to oxazolidinone enoates (2) in the presence of hexafluoroisopropanol proceeded stereoselectively to give 4-substituted butenolides in good yields. A 1:1 complex prepared in situ from Sc(OTf)(3) and 3,3'-bis(diethylaminomethyl)-1,1'-bi-2-naphthol 5b showed excellent anti-selectivity and moderate enantioselectivity, while Cu(OTf)(2)-bis(oxazoline) complex exhibited excellent enantioselectivity and moderate to good anti-selectivity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10152-1