3-[(1E,3E)-5-hydroxy-3-methylpenta-1,3-dienyl]-2,4,4-trimethyl(113C)cyclohex-2-en-1-one | 264279-45-0

• 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: 3-[(1E,3E)-5-hydroxy-3-methylpenta-1,3-dienyl]-2,4,4-trimethyl(113C)cyclohex-2-en-1-one
• CAS: 264279-45-0
• 化学式: C₁₅H₂₂O₂
• 分子量: 235.327
• InChiKey: BVUBYYWRFBEIET-GMYYHFJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-[(1E,3E)-5-hydroxy-3-methylpenta-1,3-dienyl]-2,4,4-trimethyl(113C)cyclohex-2-en-1-one 在 lithium diisopropyl amide 、 (+)-8,8-二氯樟脑磺哑嗪 作用下， 以 四氢呋喃 为溶剂， 反应 1.42h， 以68%的产率得到6-hydroxy-3-[(1E,3E)-5-hydroxy-3-methylpenta-1,3-dienyl]-2,4,4-trimethyl(113C)cyclohex-2-en-1-one
  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：

  2,6,6-trimethyl-3-oxo(313C)cyclohexene-1-carbonitrile 在 盐酸 、 正丁基锂 、 二异丁基氢化铝 、 对甲苯磺酸 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 水 、 丙酮 、 Petroleum ether 为溶剂， 反应 2.0h， 生成 3-[(1E,3E)-5-hydroxy-3-methylpenta-1,3-dienyl]-2,4,4-trimethyl(113C)cyclohex-2-en-1-one
  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