(2E,4E)-5-{3-[3,5-Diisopropyl-2-(2,2,2-trifluoro-ethoxy)-phenyl]-thiophen-2-yl}-3-methyl-penta-2,4-dienoic acid ethyl ester | 606122-91-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2E,4E)-5-{3-[3,5-Diisopropyl-2-(2,2,2-trifluoro-ethoxy)-phenyl]-thiophen-2-yl}-3-methyl-penta-2,4-dienoic acid ethyl ester
• CAS: 606122-91-2
• 化学式: C₂₆H₃₁F₃O₃S
• 分子量: 480.592
• InChiKey: GPDWWPKJEOYOEJ-VAJMCMFXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.13
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2E,4E)-5-{3-[3,5-Diisopropyl-2-(2,2,2-trifluoro-ethoxy)-phenyl]-thiophen-2-yl}-3-methyl-penta-2,4-dienoic acid ethyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以20%的产率得到5-{3-[3,5-Diisopropyl-2-(2,2,2-trifluoro-ethoxy)-phenyl]-thiophen-2-yl}-3-methyl-penta-2,4-dienoic acid
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Relationship Studies of Novel 6,7-Locked-[7-(2-alkoxy-3,5-dialkylbenzene)-3-methylocta]-2,4,6-trienoic Acids

  摘要：

  Retinoid X receptor:peroxisome proliferative-activated receptor (RXR:PPAR) heterodimers play a critical role in the regulation of glucose (RXR/PPARy) and lipid metabolism (RXR/PPARalpha). Previously, we described a concise structure-activity relationship study of selective RXR modulators possessing a (2E,4E,6Z)-3-methyl-7-(3,5-dialkyl-6-Eilkoxyphenyl)-octa-2,4,6-trienoic acid scaffold. These studies were focused on the 2-position alkoxy side chain. We describe here the design and synthesis of a novel series of RXR selective modulators possessing the same aromatic core structure with the addition of a ring locked 6--7-Z-olefin on the trienoic acid moiety. The synthesis and structure- activity relationship studies of these 6,7-locked cyclopentenyl, phenyl, thienyl, furan, and pyridine-trienoic acid derivatives is presented herein.

  DOI：

  10.1021/jm020401k
• 作为产物：
  描述：

  2,4-二异丙基苯酚 在 N,N-二甲基丙烯基脲 、 N-碘代丁二酰亚胺 、 四(三苯基膦)钯 、 正丁基锂 、 sodium carbonate 、 caesium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 18.83h， 生成 (2E,4E)-5-{3-[3,5-Diisopropyl-2-(2,2,2-trifluoro-ethoxy)-phenyl]-thiophen-2-yl}-3-methyl-penta-2,4-dienoic acid ethyl ester
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Relationship Studies of Novel 6,7-Locked-[7-(2-alkoxy-3,5-dialkylbenzene)-3-methylocta]-2,4,6-trienoic Acids

  摘要：

  Retinoid X receptor:peroxisome proliferative-activated receptor (RXR:PPAR) heterodimers play a critical role in the regulation of glucose (RXR/PPARy) and lipid metabolism (RXR/PPARalpha). Previously, we described a concise structure-activity relationship study of selective RXR modulators possessing a (2E,4E,6Z)-3-methyl-7-(3,5-dialkyl-6-Eilkoxyphenyl)-octa-2,4,6-trienoic acid scaffold. These studies were focused on the 2-position alkoxy side chain. We describe here the design and synthesis of a novel series of RXR selective modulators possessing the same aromatic core structure with the addition of a ring locked 6--7-Z-olefin on the trienoic acid moiety. The synthesis and structure- activity relationship studies of these 6,7-locked cyclopentenyl, phenyl, thienyl, furan, and pyridine-trienoic acid derivatives is presented herein.

  DOI：

  10.1021/jm020401k