ethyl (+)-(2E,4E,6Z,8E)-3,7-dimethyl-9-[(3R,6R)-6-methyl-3-(prop-1-en-2-yl)cyclohex-1-ene]nona-2,4,6,8-tetraenoate | 1093863-65-0

• 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: ethyl (+)-(2E,4E,6Z,8E)-3,7-dimethyl-9-[(3R,6R)-6-methyl-3-(prop-1-en-2-yl)cyclohex-1-ene]nona-2,4,6,8-tetraenoate
• CAS: 1093863-65-0
• 化学式: C₂₃H₃₂O₂
• 分子量: 340.506
• InChiKey: UTSIGPNPHYSBBM-RICHRWEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  ethyl (+)-(2E,4E,6Z,8E)-3,7-dimethyl-9-[(3R,6R)-6-methyl-3-(prop-1-en-2-yl)cyclohex-1-ene]nona-2,4,6,8-tetraenoate 在 氢氧化钾 、 水 、 盐酸 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以75%的产率得到(+)-(2E,4E,6Z,8E)-3,7-dimethyl-9-[(3R,6R)-6-methyl-3-(prop-1-en-2-yl)cyclohex-1-ene]nona-2,4,6,8-tetraenoic acid
  参考文献：
  名称：

  New retinoid chemotypes: 9-cis-Retinoic acid analogs with hydrophobic rings derived from terpenes as selective RAR agonists

  摘要：

  A series of 9-cis-retinoic acid analogs modified at the hydrophobic ring with a (bi)cyclohexenyl moiety derived from natural terpenes has been stereoselectively prepared using a Suzuki cross-coupling as key step. Transient transactivation studies indicate that modi. cation of the hydrophobic ring impacts dramatically on RXR-binding and transactivation, with most retinoids being inactive on RXR beta, while preserving their RAR pan-agonist pro. le. Furthermore, only the RAR gamma subtype was capable of enantiomeric discrimination with some pairs of enantiomeric terpene-retinoids. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.069
• 作为产物：
  描述：

  (+)-(2R,5R)-2-methyl-5-propen-2-ylcyclohexanone 2,4,6-triisopropylbenzenesulfonylhydrazone 、 ethyl (2E,4E,6Z,8E)-9-iodo-3,7-dimethylnona-2,4,6,8-tetraenoate 在 正丁基锂 、 硼酸三异丙酯 、 四(三苯基膦)钯 、 氢氧化铊(Ⅰ) 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 0.5h， 以68%的产率得到ethyl (+)-(2E,4E,6Z,8E)-3,7-dimethyl-9-[(3R,6R)-6-methyl-3-(prop-1-en-2-yl)cyclohex-1-ene]nona-2,4,6,8-tetraenoate
  参考文献：
  名称：

  New retinoid chemotypes: 9-cis-Retinoic acid analogs with hydrophobic rings derived from terpenes as selective RAR agonists

  摘要：

  A series of 9-cis-retinoic acid analogs modified at the hydrophobic ring with a (bi)cyclohexenyl moiety derived from natural terpenes has been stereoselectively prepared using a Suzuki cross-coupling as key step. Transient transactivation studies indicate that modi. cation of the hydrophobic ring impacts dramatically on RXR-binding and transactivation, with most retinoids being inactive on RXR beta, while preserving their RAR pan-agonist pro. le. Furthermore, only the RAR gamma subtype was capable of enantiomeric discrimination with some pairs of enantiomeric terpene-retinoids. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.09.069