ethyl-2-[3,5-di-iso-propyl-2-(2,2,2-trifluoroethoxy)benzene]cyclopentene-1-carboxylate | 606123-05-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl-2-[3,5-di-iso-propyl-2-(2,2,2-trifluoroethoxy)benzene]cyclopentene-1-carboxylate
• 英文别名: Ethyl 2-[3,5-di(propan-2-yl)-2-(2,2,2-trifluoroethoxy)phenyl]cyclopentene-1-carboxylate
• CAS: 606123-05-1
• 化学式: C₂₂H₂₉F₃O₃
• 分子量: 398.466
• InChiKey: MEHMIWNYJOTOLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl-2-[3,5-di-iso-propyl-2-(2,2,2-trifluoroethoxy)benzene]cyclopentene-1-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以97%的产率得到1-[3,5-di-iso-propyl-2-(2,2,2-trifluoroethoxy)benzene]cyclopentene-2-methanol
  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 盐酸 、 N-碘代丁二酰亚胺 、 四(三苯基膦)钯 、 正丁基锂 、 四甲基乙二胺 、 sodium carbonate 、 caesium carbonate 、 对甲苯磺酸 作用下， 以 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 17.25h， 生成 ethyl-2-[3,5-di-iso-propyl-2-(2,2,2-trifluoroethoxy)benzene]cyclopentene-1-carboxylate
  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

文献信息

• 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
  作者：Pierre-Yves Michellys、Robert J. Ardecky、Jyun-Hung Chen、Jennifer D'Arrigo、Timothy A. Grese、Donald S. Karanewsky、Mark D. Leibowitz、Sha Liu、Dale A. Mais、Christopher M. Mapes、Chahrzad Montrose-Rafizadeh、Katheen M. Ogilvie、Anne Reifel-Miller、Deepa Rungta、Anthony W. Thompson、John S. Tyhonas、Marcus F. Boehm

  DOI：10.1021/jm020401k

  日期：2003.9.1

  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.