Ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexa-1,4-dien-1-yl)nonatetraenoate | 162376-87-6

• 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,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexa-1,4-dien-1-yl)nonatetraenoate
• 英文别名: ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1,4-dienyl)-nona-2,4,6,8-tetraenoate；ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexa-1,4-dien-1-yl)nona-2,4,6,8-tetraenoate
• CAS: 162376-87-6
• 化学式: C₂₂H₃₀O₂
• 分子量: 326.479
• InChiKey: HGWCABZEQBEVDU-MTJYDOFUSA-N

物化性质

• 沸点：
  441.9±14.0 °C(Predicted)
• 密度：
  0.982±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexa-1,4-dien-1-yl)nonatetraenoate 在 Rh(PPh₃)Cl sodium hydroxide 、 氢气 作用下， 以 乙醇 、 苯 为溶剂， 反应 2.0h， 生成 9-顺式维甲酸
  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：

  5,6-Dihydro-4-methyl-6-(2,6,6-trimethylcyclohexa-1,4-dien-1-yl)-2H-pyran-2-ol 在 盐酸 N,N-二甲基丙烯基脲 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 1,2-二氯乙烷 为溶剂， 反应 1.33h， 生成 Ethyl (2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexa-1,4-dien-1-yl)nonatetraenoate
  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

文献信息

• Ring-labeled retinoids and intermediates, and methods for their
  申请人：Ligand Pharmaceuticals Incorporated

  公开号：US05514821A1

  公开（公告）日：1996-05-07

  Methods for the synthesis of dideuterium and/or ditritium ring-labeled retinoids and intermediates, and their use in the discovery of Retinoid X Receptor ligands are provided. In addition, dideuterium and/or ditritium ring-labeled retinoids and novel intermediates, as well as methods for their use in ligand binding and mass spectral studies are also provided.

  本发明提供了合成二氘和/或二氚环标记视黄醇类化合物和中间体的方法，并将其用于发现视黄酸X受体配体。此外，本发明还提供了二氘和/或二氚环标记的视黄醇类化合物和新型中间体，以及将它们用于配体结合和质谱研究的方法。