2-Z-5-((4'R)-4'-hydroxy-2',2',6'-trimethylcyclohex-1'-enyl)-3-methyl-2-penten-4-yn-1-al | 160332-75-2

• 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: 2-Z-5-((4'R)-4'-hydroxy-2',2',6'-trimethylcyclohex-1'-enyl)-3-methyl-2-penten-4-yn-1-al
• 英文别名: (Z)-5-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-3-methylpent-2-en-4-ynal
• CAS: 160332-75-2
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: GZUYXUHVLCGNAS-LWMSPQMPSA-N

物化性质

• 沸点：
  352.5±42.0 °C(predicted)
• 密度：
  1.04±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：

  <(3R)-3-hydroxy-12'-apo-β-carotenyl>triphenylphosphonium bromide 、 2-Z-5-((4'R)-4'-hydroxy-2',2',6'-trimethylcyclohex-1'-enyl)-3-methyl-2-penten-4-yn-1-al 在 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 9-Z-(3R,3'R)-diatoxanthin
  参考文献：
  名称：

  Total synthesis of acetylenic carotenoids.

  摘要：

  Optically active 9-Z(3R,3'R)-diatoxanthin and 9-Z(3R)-7,8-didehydrocryptoxanthin were synthesised in an overall yield of 9% and 11% respectively, with a seven step C-9+C-6+C-25=C-40 strategy. A key intermediate was the previously undescribed C-15-acetylenic aldehyde 2-Z-5-((4'R)-4'-hydroxy-2',6',6'-trimethylcyclohex-1'-enyl)-3-methyl-2-penten-4-yn-1-al.Observed isomerisation shifts for the title compounds relative to the all-E isomers in H-1 NMR and C-13 NMR were as expected. CD properties are discussed.

  DOI：

  10.1016/0957-4166(94)80087-1
• 作为产物：
  描述：

  (4R*,6R*)-2,2,6-Trimethyl-4-hydroxycyclohexan-1-one 在 manganese(IV) oxide 、 氢氧化钾 、 potassium hydrogensulfate 、 乙基溴化镁 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 54.75h， 生成 2-Z-5-((4'R)-4'-hydroxy-2',2',6'-trimethylcyclohex-1'-enyl)-3-methyl-2-penten-4-yn-1-al
  参考文献：
  名称：

  Total synthesis of acetylenic carotenoids.

  摘要：

  Optically active 9-Z(3R,3'R)-diatoxanthin and 9-Z(3R)-7,8-didehydrocryptoxanthin were synthesised in an overall yield of 9% and 11% respectively, with a seven step C-9+C-6+C-25=C-40 strategy. A key intermediate was the previously undescribed C-15-acetylenic aldehyde 2-Z-5-((4'R)-4'-hydroxy-2',6',6'-trimethylcyclohex-1'-enyl)-3-methyl-2-penten-4-yn-1-al.Observed isomerisation shifts for the title compounds relative to the all-E isomers in H-1 NMR and C-13 NMR were as expected. CD properties are discussed.

  DOI：

  10.1016/0957-4166(94)80087-1

文献信息

• Total synthesis of acetylenic carotenoids.
  作者：Jarle André Haugan、Synnøve Liaaen-Jensen

  DOI：10.1016/0957-4166(94)80087-1

  日期：1994.9

  Optically active 9-Z(3R,3'R)-diatoxanthin and 9-Z(3R)-7,8-didehydrocryptoxanthin were synthesised in an overall yield of 9% and 11% respectively, with a seven step C-9+C-6+C-25=C-40 strategy. A key intermediate was the previously undescribed C-15-acetylenic aldehyde 2-Z-5-((4'R)-4'-hydroxy-2',6',6'-trimethylcyclohex-1'-enyl)-3-methyl-2-penten-4-yn-1-al.Observed isomerisation shifts for the title compounds relative to the all-E isomers in H-1 NMR and C-13 NMR were as expected. CD properties are discussed.