(-)-pulegone tosylhydrazone | 122407-23-2

• 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: (-)-pulegone tosylhydrazone
• 英文别名: (+)-Pulegontosylhydrazon
• CAS: 122407-23-2
• 化学式: C₁₇H₂₄N₂O₂S
• 分子量: 320.456
• InChiKey: XECDZLUTPYKAHE-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  58.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (-)-pulegone tosylhydrazone 、 ethyl (2E,4E,6Z,8E)-9-iodo-3,7-dimethylnona-2,4,6,8-tetraenoate 在 四甲基乙二胺 、 甲基锂 、 硼酸三异丙酯 、 四(三苯基膦)钯 、 氢氧化铊(Ⅰ) 作用下， 以 乙醚 、 水 为溶剂， 反应 0.5h， 以63%的产率得到ethyl (+)-(2E,4E,6Z,8E)-3,7-dimethyl-9-[(R)-5-methyl-2-(1-methylethen-1-yl)cyclohex-1-en-1-yl]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
• 作为产物：
  描述：

  长叶薄荷酮 、 对甲苯磺酰肼 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以92%的产率得到(-)-pulegone tosylhydrazone
  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