3-[4-(4-hydroxy-3-isopropylbenzyl)-3,5-dimethylphenyl]acrylic acid benzyl ester | 565452-50-8

• 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: 3-[4-(4-hydroxy-3-isopropylbenzyl)-3,5-dimethylphenyl]acrylic acid benzyl ester
• 英文别名: benzyl (E)-3-[4-[(4-hydroxy-3-propan-2-ylphenyl)methyl]-3,5-dimethylphenyl]prop-2-enoate
• CAS: 565452-50-8
• 化学式: C₂₈H₃₀O₃
• 分子量: 414.544
• InChiKey: TUGDSNSQORUATM-ACCUITESSA-N

物化性质

• 沸点：
  569.0±45.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[4-(4-hydroxy-3-isopropylbenzyl)-3,5-dimethylphenyl]acrylic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以90%的产率得到3-[4-(4-Hydroxy-3-isopropyl-benzyl)-3,5-dimethyl-phenyl]-propionic acid
  参考文献：
  名称：

  Structural Determinants of Selective Thyromimetics

  摘要：

  The thyromimetic GC-1 shows a preference for binding the P form of the thyroid hormone receptor (TR). GC-1 was designed as an analogue of the thyromimetic DIMIT, which has alower affinity for TR and is not selective. GC-1 has a methylene group linking its two aromatic rings and an oxyacetic acid polar side chain, while DIMIT has an ether oxygen linking its aromatic rings and an L-alanine polar side chain. The structural features of GC-1 that confer its greater affinity and selectivity compared to DIMIT were analyzed with the preparation of analogues that bear only one of their two different structural features. The analogue of GC-1 with a biaryl ether has selectivity comparable to that of GC-1, while the analogue of DIMIT with a methylene group linking its aromatic rings is only slightly selective. These results demonstrate that the oxyacetic acid side chain of GC-1 is critical in conferring TR-beta selectivity.

  DOI：

  10.1021/jm0301181
• 作为产物：
  描述：

  4-溴-2-异丙基苯酚 在 palladium on activated charcoal 吡啶 、 咪唑 、 bis-triphenylphosphine-palladium(II) chloride 、 正丁基锂 、 氢气 、 臭氧 、 triethylamine tris(hydrogen fluoride) 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 乙酸乙酯 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， -78.0~60.0 ℃ 、241.32 kPa 条件下， 反应 34.5h， 生成 3-[4-(4-hydroxy-3-isopropylbenzyl)-3,5-dimethylphenyl]acrylic acid benzyl ester
  参考文献：
  名称：

  Structural Determinants of Selective Thyromimetics

  摘要：

  The thyromimetic GC-1 shows a preference for binding the P form of the thyroid hormone receptor (TR). GC-1 was designed as an analogue of the thyromimetic DIMIT, which has alower affinity for TR and is not selective. GC-1 has a methylene group linking its two aromatic rings and an oxyacetic acid polar side chain, while DIMIT has an ether oxygen linking its aromatic rings and an L-alanine polar side chain. The structural features of GC-1 that confer its greater affinity and selectivity compared to DIMIT were analyzed with the preparation of analogues that bear only one of their two different structural features. The analogue of GC-1 with a biaryl ether has selectivity comparable to that of GC-1, while the analogue of DIMIT with a methylene group linking its aromatic rings is only slightly selective. These results demonstrate that the oxyacetic acid side chain of GC-1 is critical in conferring TR-beta selectivity.

  DOI：

  10.1021/jm0301181

文献信息

• Structural Determinants of Selective Thyromimetics
  作者：Hikari A. I. Yoshihara、James W. Apriletti、John D. Baxter、Thomas S. Scanlan

  DOI：10.1021/jm0301181

  日期：2003.7.1

  The thyromimetic GC-1 shows a preference for binding the P form of the thyroid hormone receptor (TR). GC-1 was designed as an analogue of the thyromimetic DIMIT, which has alower affinity for TR and is not selective. GC-1 has a methylene group linking its two aromatic rings and an oxyacetic acid polar side chain, while DIMIT has an ether oxygen linking its aromatic rings and an L-alanine polar side chain. The structural features of GC-1 that confer its greater affinity and selectivity compared to DIMIT were analyzed with the preparation of analogues that bear only one of their two different structural features. The analogue of GC-1 with a biaryl ether has selectivity comparable to that of GC-1, while the analogue of DIMIT with a methylene group linking its aromatic rings is only slightly selective. These results demonstrate that the oxyacetic acid side chain of GC-1 is critical in conferring TR-beta selectivity.