ethyl (2E,4E)-3-methyl-5-(2,10,10-trimethyl-4,7-dioxaspiro[4,5]dec-1-en-1-yl)-2,4-pentadienoate | 264279-25-6

• 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: ethyl (2E,4E)-3-methyl-5-(2,10,10-trimethyl-4,7-dioxaspiro[4,5]dec-1-en-1-yl)-2,4-pentadienoate
• 英文别名: ethyl (2E,4E)-3-methyl-5-(6,8,8-trimethyl-1,4-dioxaspiro[4.5]dec-6-en-7-yl)penta-2,4-dienoate
• CAS: 264279-25-6
• 化学式: C₁₉H₂₈O₄
• 分子量: 320.429
• InChiKey: WROSTOGWHIRYTD-SCCLZRITSA-N

物化性质

• 沸点：
  423.7±40.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (2E,4E)-3-methyl-5-(2,10,10-trimethyl-4,7-dioxaspiro[4,5]dec-1-en-1-yl)-2,4-pentadienoate 在 二异丁基氢化铝 作用下， 以 Petroleum ether 为溶剂， 以52%的产率得到(2E,4E)-3-methyl-5-(2,10,10-trimethyl-4,7-dioxaspiro[4,5]dec-1-en-1-yl)-2,4-pentadienol
  参考文献：
  名称：

  Synthesis and Characterization ofall-E-(4,4′-13C2)-Astaxanthin Strategies for Labelling the C15-End Groups of Carotenoids

  摘要：

  The all-E isomer of (4,4'-C-13(2))astaxanthin (1a) has been prepared by total synthesis starting from commercially available 99% C-13 enriched acetonitrile. The labelled astaxanthin was obtained in high purity and with high isotope incorporation. For this synthesis, the C-15 + C-10 + C-15 strategy was used. The central C-10-synthon, 2,7-dimethylocta-2,4,6-triene-1,8-dial (3), was coupled with C-13-enriched C-15-phosphonium salt 2a. The new synthetic scheme for the preparation of the C-15-phosphonium salt is discussed in this paper; the same scheme can be used to label all positions and combinations of positions of the C-15-phosphonium salt.

  DOI：

  10.1002/(sici)1099-0690(200003)2000:5<829::aid-ejoc829>3.0.co;2-z
• 作为产物：
  描述：

  6-甲基-5-庚烯-2-酮 在 正丁基锂 、 硫酸 、 sodium hydride 、 二异丁基氢化铝 、 对甲苯磺酸 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 、 lithium diisopropyl amide 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 硝基甲烷 、 二氯甲烷 、 乙酸乙酯 、 Petroleum ether 为溶剂， 反应 4.5h， 生成 ethyl (2E,4E)-3-methyl-5-(2,10,10-trimethyl-4,7-dioxaspiro[4,5]dec-1-en-1-yl)-2,4-pentadienoate
  参考文献：
  名称：

  Synthesis and Characterization ofall-E-(4,4′-13C2)-Astaxanthin Strategies for Labelling the C15-End Groups of Carotenoids

  摘要：

  The all-E isomer of (4,4'-C-13(2))astaxanthin (1a) has been prepared by total synthesis starting from commercially available 99% C-13 enriched acetonitrile. The labelled astaxanthin was obtained in high purity and with high isotope incorporation. For this synthesis, the C-15 + C-10 + C-15 strategy was used. The central C-10-synthon, 2,7-dimethylocta-2,4,6-triene-1,8-dial (3), was coupled with C-13-enriched C-15-phosphonium salt 2a. The new synthetic scheme for the preparation of the C-15-phosphonium salt is discussed in this paper; the same scheme can be used to label all positions and combinations of positions of the C-15-phosphonium salt.

  DOI：

  10.1002/(sici)1099-0690(200003)2000:5<829::aid-ejoc829>3.0.co;2-z