(E)-3-[(4S,5S)-5-((E)-2-Methoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acrylic acid methyl ester | 913549-42-5

• 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: (E)-3-[(4S,5S)-5-((E)-2-Methoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acrylic acid methyl ester
• CAS: 913549-42-5
• 化学式: C₁₃H₁₈O₆
• 分子量: 270.282
• InChiKey: CMZOUPWUYOCRDR-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.96
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (-)-二甲基-2,3-邻异丙亚基-L-酒石酸酯 在 二异丁基氢化铝 作用下， 生成 (E)-3-[(4S,5S)-5-((E)-2-Methoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acrylic acid methyl ester
  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

• New chiral monodentate phospholane ligands by highly stereoselective hydrophosphination
  作者：Vitaliy Bilenko、Anke Spannenberg、Wolfgang Baumann、Igor Komarov、Armin Börner

  DOI：10.1016/j.tetasy.2006.06.047

  日期：2006.8

  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.