(5S)-5-[(2S)-5-oxo-2,5-dihydro-2-furanyl]-2,5-dihydro-2-furanone | 155103-45-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (5S)-5-[(2S)-5-oxo-2,5-dihydro-2-furanyl]-2,5-dihydro-2-furanone
• 英文别名: 5(H)-2-bisfuranone；(2S)-2-[(2S)-5-oxo-2H-furan-2-yl]-2H-furan-5-one
• CAS: 155103-45-0
• 化学式: C₈H₆O₄
• 分子量: 166.133
• InChiKey: VCHDYHWRVCLEJK-WDSKDSINSA-N

物化性质

• 熔点：
  184 °C(Solvent: Hexane; Ethanol)
• 沸点：
  487.2±45.0 °C(predicted)
• 密度：
  1.473±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.05
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (5S)-5-[(2S)-5-oxo-2,5-dihydro-2-furanyl]-2,5-dihydro-2-furanone 在 三乙烯二胺 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (3aR,4aR,7aR,7bR)-4-cyclohexylperhydrofuro[2',3':4,5]phospholo[3,2-b]furan-2,6-dione
  参考文献：
  名称：

  New chiral monodentate phospholane ligands by highly stereoselective hydrophosphination

  摘要：

  New chiral phospholanes 6 were prepared in both enantiomeric forms starting from L- and D-tartaric acid. The key step in the synthetic sequence is the double hydrophosphination of unsaturated chiral bis(lactone) 9 by NaPhPH(BH3). This method was used for the first time in the formation of chiral phospholanes. The structure of phospholane 6a was confirmed by X-ray crystallography. sigma-Donor properties of the phospholanes were estimated by measurement of (1)J((PSe)-P-31-Se-77) coupling constants in the corresponding phosphine selenides. The new phospholanes were tested as ligands in the Rh-catalyzed enantioselective hydrogenation of functionalized standard olefins (65-92% ee). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.047
• 作为产物：
  描述：

  (E)-3-[(4S,5S)-5-((E)-2-Methoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acrylic acid methyl ester 在 甲烷磺酸 、 水 作用下， 以 乙二醇二甲醚 为溶剂， 以4.7 g的产率得到(5S)-5-[(2S)-5-oxo-2,5-dihydro-2-furanyl]-2,5-dihydro-2-furanone
  参考文献：
  名称：

  New chiral monodentate phospholane ligands by highly stereoselective hydrophosphination

  摘要：

  New chiral phospholanes 6 were prepared in both enantiomeric forms starting from L- and D-tartaric acid. The key step in the synthetic sequence is the double hydrophosphination of unsaturated chiral bis(lactone) 9 by NaPhPH(BH3). This method was used for the first time in the formation of chiral phospholanes. The structure of phospholane 6a was confirmed by X-ray crystallography. sigma-Donor properties of the phospholanes were estimated by measurement of (1)J((PSe)-P-31-Se-77) coupling constants in the corresponding phosphine selenides. The new phospholanes were tested as ligands in the Rh-catalyzed enantioselective hydrogenation of functionalized standard olefins (65-92% ee). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.047

文献信息

• Novel Strategy for the Bis-Butenolide Synthesis via Ring-Closing Metathesis
  作者：Christophe Len、Muriel Billamboz、Jean Legeay、Frédéric Hapiot、Eric Monflier

  DOI：10.1055/s-0031-1289621

  日期：2012.1

  A new synthesis to bis-butenolide derivatives from inexpensive divinylglycol is described, employing a sequential double acylation followed by a double ring-closing metathesis. The selectivity is affected by the choice of catalyst.

  一种从廉价的二乙烯甘油合成双丁烯内酯衍生物的新方法被报道，该方法采用连续的双酰化反应，随后进行双环化关环复分解反应。选择性受到催化剂选择的影响。
• Stereoselective synthesis of new functionalized bisphosphines
  作者：Yann Gourdel、Pascal Pellon、Loïc Toupet、Maurice Le Corre

  DOI：10.1016/0040-4039(94)88022-0

  日期：1994.2

  Chiral functionalized bisdiphenylphosphines have been prepared and isolated from natural tartaric acid via the dihydrophosphorylation of dimethyl 4,5-O-isopropylidene-2,6-octanedienedioate, 4,5-O-isopropylidene-2,6-octanedienedinitrile and bis 5 (H)-2-furanone.

  已通过4,5-O-异亚丙基-2,6-辛二烯二酸二甲酯，4,5-O-异亚丙基-2,6-辛二烯二init酸酯和bis 5（H）的二氢磷酸化反应制备了手性官能化的双二苯基膦并从天然酒石酸中分离出-2-呋喃酮。