(3S,4R,5S)-5-丁基-5-乙氧基-3,4-二羟基二氢-2(3H)-呋喃酮 | 169396-07-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (3S,4R,5S)-5-丁基-5-乙氧基-3,4-二羟基二氢-2(3H)-呋喃酮
• 英文名称: (3S,4R,5S)-5-Butyl-5-ethoxy-3,4-dihydroxy-dihydro-furan-2-one
• 英文别名: (3S,4R,5S)-5-butyl-5-ethoxy-3,4-dihydroxyoxolan-2-one
• CAS: 169396-07-0
• 化学式: C₁₀H₁₈O₅
• 分子量: 218.25
• InChiKey: YNOAXFAKHFTGJD-XKSSXDPKSA-N

物化性质

• 沸点：
  331.7±31.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  对甲苯磺酰氯 、 (3S,4R,5S)-5-丁基-5-乙氧基-3,4-二羟基二氢-2(3H)-呋喃酮 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以93%的产率得到Toluene-4-sulfonic acid (3S,4R,5S)-5-butyl-5-ethoxy-4-hydroxy-2-oxo-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Asymmetric Functionalization of Chromium Carbene-Derived Optically Active 4,4-Disubstituted Butenolides

  摘要：

  Optically active 4,4-disubstituted butenolides were readily prepared by photolysis of chromium alkoxycarbene complexes with optically active ene carbamates, followed by Baeyer-Villiger oxidation/oxazolidinone elimination. These butenolides underwent clean 1,3-dipolar cycloaddition reactions with cyclic nitrones exclusively from the more hindered face of the butenolide. Azomethine ylides were considerably less stereoselective. Conjugate addition reactions also occurred from the more hindered face, while cis hydroxylation occurred from the opposite face.

  DOI：

  10.1021/jo00117a034
• 作为产物：
  描述：

  (5S)-5-butyl-5-ethoxyfuran-2-one 在 二环己烷并-18-冠醚-6 、 potassium permanganate 作用下， 以 二氯甲烷 为溶剂， 以66%的产率得到(3S,4R,5S)-5-丁基-5-乙氧基-3,4-二羟基二氢-2(3H)-呋喃酮
  参考文献：
  名称：

  Asymmetric Functionalization of Chromium Carbene-Derived Optically Active 4,4-Disubstituted Butenolides

  摘要：

  Optically active 4,4-disubstituted butenolides were readily prepared by photolysis of chromium alkoxycarbene complexes with optically active ene carbamates, followed by Baeyer-Villiger oxidation/oxazolidinone elimination. These butenolides underwent clean 1,3-dipolar cycloaddition reactions with cyclic nitrones exclusively from the more hindered face of the butenolide. Azomethine ylides were considerably less stereoselective. Conjugate addition reactions also occurred from the more hindered face, while cis hydroxylation occurred from the opposite face.

  DOI：

  10.1021/jo00117a034

文献信息

• Asymmetric Functionalization of Chromium Carbene-Derived Optically Active 4,4-Disubstituted Butenolides
  作者：A. D. Reed、Louis S. Hegedus

  DOI：10.1021/jo00117a034

  日期：1995.6

  Optically active 4,4-disubstituted butenolides were readily prepared by photolysis of chromium alkoxycarbene complexes with optically active ene carbamates, followed by Baeyer-Villiger oxidation/oxazolidinone elimination. These butenolides underwent clean 1,3-dipolar cycloaddition reactions with cyclic nitrones exclusively from the more hindered face of the butenolide. Azomethine ylides were considerably less stereoselective. Conjugate addition reactions also occurred from the more hindered face, while cis hydroxylation occurred from the opposite face.