5-[4-[(E)-(3-ethyl-2,4,4-trimethylcyclohex-2-en-1-ylidene)methyl]phenyl]-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,2,4-oxadiazole | 1307916-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-[4-[(E)-(3-ethyl-2,4,4-trimethylcyclohex-2-en-1-ylidene)methyl]phenyl]-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,2,4-oxadiazole
• CAS: 1307916-59-1
• 化学式: C₃₂H₃₉BN₂O₃
• 分子量: 510.484
• InChiKey: GSGJXYXCJQOWJE-LKUDQCMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.63
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  57.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (E)-4-((3-ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium acetate 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.7h， 生成 5-[4-[(E)-(3-ethyl-2,4,4-trimethylcyclohex-2-en-1-ylidene)methyl]phenyl]-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,2,4-oxadiazole
  参考文献：
  名称：

  Design and synthesis of 3,5-disubstituted 1,2,4-oxadiazole containing retinoids from a retinoic acid receptor agonist

  摘要：

  We previously synthesized novel retinoid libraries, and after screening for bioactivity found one compound BT10 that functions as a specific agonist for retinoic acid receptors. This lead compound was further derivatized using SAR and LRD to obtain 3,5-disubstituted-1,2,4-oxadiazole-containing retinoids. The new oxadiazole (amide bioisosters)-containing retinoids (compounds 1, 2, 3, 4, 5, and 6) were synthesized in 42-65% yield by reacting with (E)-4-((3-ethy1,2-4,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid and phenyl substituted amidoxime in DMF using CDI as the coupling reagent. The biological activities of the synthesized compounds are currently being evaluated. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.011

文献信息

• Design and synthesis of 3,5-disubstituted 1,2,4-oxadiazole containing retinoids from a retinoic acid receptor agonist
  作者：Bhaskar C. Das、Xiang-Ying Tang、Swarnava Sanyal、Seetaram Mohapatra、Patrick Rogler、Sabita Nayak、Todd Evans

  DOI：10.1016/j.tetlet.2011.03.011

  日期：2011.5

  We previously synthesized novel retinoid libraries, and after screening for bioactivity found one compound BT10 that functions as a specific agonist for retinoic acid receptors. This lead compound was further derivatized using SAR and LRD to obtain 3,5-disubstituted-1,2,4-oxadiazole-containing retinoids. The new oxadiazole (amide bioisosters)-containing retinoids (compounds 1, 2, 3, 4, 5, and 6) were synthesized in 42-65% yield by reacting with (E)-4-((3-ethy1,2-4,4,4-trimethylcyclohex-2-enylidene)methyl)benzoic acid and phenyl substituted amidoxime in DMF using CDI as the coupling reagent. The biological activities of the synthesized compounds are currently being evaluated. (C) 2011 Elsevier Ltd. All rights reserved.