(2Z,4E)-5-(3,5-ditert-butylphenyl)-3-methylpenta-2,4-dien-1-ol | 823192-19-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2Z,4E)-5-(3,5-ditert-butylphenyl)-3-methylpenta-2,4-dien-1-ol
• CAS: 823192-19-4
• 化学式: C₂₀H₃₀O
• 分子量: 286.458
• InChiKey: RXKNAHBZIDEWKE-QCAIBQKMSA-N

物化性质

• 沸点：
  380.4±11.0 °C(Predicted)
• 密度：
  0.941±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (2Z,4E)-5-(3,5-ditert-butylphenyl)-3-methylpenta-2,4-dien-1-ol 在 N,N-二甲基丙烯基脲 、 氢氧化钾 、 正丁基锂 、 N-甲基吲哚酮 、 四丙基高钌酸铵 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2E,4E,6Z,8E)-9-(3,5-ditert-butylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
  参考文献：
  名称：

  9-cis-Retinoic acid analogues with bulky hydrophobic rings: new RXR-selective agonists

  摘要：

  Stille cross-coupling of aryltriflates 10 and dienylstannane 11, oxidation and Horner-Wadsworth-Emmons reaction afforded stereoselectively retinoates 15. Saponification provided the carboxylic acids 8a and 86, retinoids that incorporate a bulky hydrophobic ring while preserving the 9-cis-geometry of the parent system. In contrast to the pan-RAR/RXR agonistic profile of the lower homologue of 8a, compound 7 (LG100567), retinoids 8 showed selective binding and transactivation of RXR, devoid of significant RAR activation. In PLB985 leukemia cells that require RXR agonists for differentiation compounds 8 induced maturation in the presence of the RAR-selective pan-agonist TTNPB; this effect was blocked by an RXR-selective antagonist. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.072
• 作为产物：
  描述：

  3,5-二叔丁基苯酚 在 tris(dibenzylideneacetone)dipalladium (0) 、 三苯胂 、 三乙胺 、 lithium chloride 作用下， 以 N-甲基吡咯烷酮 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 (2Z,4E)-5-(3,5-ditert-butylphenyl)-3-methylpenta-2,4-dien-1-ol
  参考文献：
  名称：

  9-cis-Retinoic acid analogues with bulky hydrophobic rings: new RXR-selective agonists

  摘要：

  Stille cross-coupling of aryltriflates 10 and dienylstannane 11, oxidation and Horner-Wadsworth-Emmons reaction afforded stereoselectively retinoates 15. Saponification provided the carboxylic acids 8a and 86, retinoids that incorporate a bulky hydrophobic ring while preserving the 9-cis-geometry of the parent system. In contrast to the pan-RAR/RXR agonistic profile of the lower homologue of 8a, compound 7 (LG100567), retinoids 8 showed selective binding and transactivation of RXR, devoid of significant RAR activation. In PLB985 leukemia cells that require RXR agonists for differentiation compounds 8 induced maturation in the presence of the RAR-selective pan-agonist TTNPB; this effect was blocked by an RXR-selective antagonist. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.072

文献信息

• 9-cis-Retinoic acid analogues with bulky hydrophobic rings: new RXR-selective agonists
  作者：Rosana Alvarez、M. Jesús Vega、Sabrina Kammerer、Aurélie Rossin、Pierre Germain、Hinrich Gronemeyer、Angel R. de Lera

  DOI：10.1016/j.bmcl.2004.08.072

  日期：2004.12

  Stille cross-coupling of aryltriflates 10 and dienylstannane 11, oxidation and Horner-Wadsworth-Emmons reaction afforded stereoselectively retinoates 15. Saponification provided the carboxylic acids 8a and 86, retinoids that incorporate a bulky hydrophobic ring while preserving the 9-cis-geometry of the parent system. In contrast to the pan-RAR/RXR agonistic profile of the lower homologue of 8a, compound 7 (LG100567), retinoids 8 showed selective binding and transactivation of RXR, devoid of significant RAR activation. In PLB985 leukemia cells that require RXR agonists for differentiation compounds 8 induced maturation in the presence of the RAR-selective pan-agonist TTNPB; this effect was blocked by an RXR-selective antagonist. (C) 2004 Elsevier Ltd. All rights reserved.