(2Z,4E)-5-(6-tert-Butyl-1,1-dimethyl-indan-4-yl)-3-methyl-penta-2,4-dienal | 823192-24-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (2Z,4E)-5-(6-tert-Butyl-1,1-dimethyl-indan-4-yl)-3-methyl-penta-2,4-dienal
• CAS: 823192-24-1
• 化学式: C₂₁H₂₈O
• 分子量: 296.453
• InChiKey: SCYWKTJLRFKSQV-XDOICYCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 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：
  0.48
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (2Z,4E)-5-(6-tert-Butyl-1,1-dimethyl-indan-4-yl)-3-methyl-penta-2,4-dienal 在 N,N-二甲基丙烯基脲 、 氢氧化钾 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 (2E,4E,6Z,8E)-9-(6-tert-Butyl-1,1-dimethyl-indan-4-yl)-3,7-dimethyl-nona-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：

  2,4-Pentadien-1-ol,5-[6-(1,1-dimethylethyl)-2,3-dihydro-1,1-dimethyl-1H-inden-4-yl]-3-methyl-, (2Z,4E)- 在 N-甲基吲哚酮 、 四丙基高钌酸铵 作用下， 以 二氯甲烷 为溶剂， 以60%的产率得到(2Z,4E)-5-(6-tert-Butyl-1,1-dimethyl-indan-4-yl)-3-methyl-penta-2,4-dienal
  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