5,6-Dihydro-4-methyl-6-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)-2H-pyran-2-ol | 162376-77-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,6-Dihydro-4-methyl-6-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)-2H-pyran-2-ol
• 英文别名: 4-methyl-2-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)-3,6-dihydro-2H-pyran-6-ol
• CAS: 162376-77-4
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: NGVFDOAZRPUXQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5,6-Dihydro-4-methyl-6-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)-2H-pyran-2-ol 在 盐酸 作用下， 以 1,2-二氯乙烷 为溶剂， 以87%的产率得到(2Z,4E)-3-Methyl-5-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)penta-2,4-dien-1-al
  参考文献：
  名称：

  Syntheses of High Specific Activity 2,3- and 3,4-[3H]2-9-cis-Retinoic Acid

  摘要：

  B-cis-Retinoic acid (9-cis-RA) is an endogenous hormone which binds and activates the retinoic acid receptors (RARs) and the retinoic X receptors (RXRs). In order to investigate the function of 9-cis-RA in vitro and in vivo high specific activity labeled 9-cis-RA was prepared. Two tritium labels were efficiently introduced at the 2,3- or 3,4-positions, respectively, in the cyclohexene ring moiety resulting in labeled 9-cis-RA with specific activity of 58-60 Ci/mmol. The critical ring-labeling step relies on a highly regioselective tritiation of either a terminal or an isolated double bond in the presence of the conjugated retinoate side chain. Moreover, the labeling is performed at the penultimate synthetic step resulting in optimization of radiochemical yields and ease of synthesis. This is the first reported synthesis of ring-labeled [H-3](2)-9-cis-RA, and the methodology described herein is applicable to the synthesis of other retinoic acid isomers.

  DOI：

  10.1021/jo00110a023
• 作为产物：
  描述：

  3-甲基-2-丁烯酸乙酯 在 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 0.75h， 生成 5,6-Dihydro-4-methyl-6-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)-2H-pyran-2-ol
  参考文献：
  名称：

  Syntheses of High Specific Activity 2,3- and 3,4-[3H]2-9-cis-Retinoic Acid

  摘要：

  B-cis-Retinoic acid (9-cis-RA) is an endogenous hormone which binds and activates the retinoic acid receptors (RARs) and the retinoic X receptors (RXRs). In order to investigate the function of 9-cis-RA in vitro and in vivo high specific activity labeled 9-cis-RA was prepared. Two tritium labels were efficiently introduced at the 2,3- or 3,4-positions, respectively, in the cyclohexene ring moiety resulting in labeled 9-cis-RA with specific activity of 58-60 Ci/mmol. The critical ring-labeling step relies on a highly regioselective tritiation of either a terminal or an isolated double bond in the presence of the conjugated retinoate side chain. Moreover, the labeling is performed at the penultimate synthetic step resulting in optimization of radiochemical yields and ease of synthesis. This is the first reported synthesis of ring-labeled [H-3](2)-9-cis-RA, and the methodology described herein is applicable to the synthesis of other retinoic acid isomers.

  DOI：

  10.1021/jo00110a023