ethyl 4-(5-(5,5-dimethyl-8-(phenylethynyl)-5,6-dihydronaphthalen-2-yl)-1,2,4-oxadiazol-3-yl)benzoate | 1360573-20-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 4-(5-(5,5-dimethyl-8-(phenylethynyl)-5,6-dihydronaphthalen-2-yl)-1,2,4-oxadiazol-3-yl)benzoate
• CAS: 1360573-20-1
• 化学式: C₃₁H₂₆N₂O₃
• 分子量: 474.559
• InChiKey: QCKHNQKTUVAJCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  36.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  65.22
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-(5-(5,5-dimethyl-8-(phenylethynyl)-5,6-dihydronaphthalen-2-yl)-1,2,4-oxadiazol-3-yl)benzoate 在 lithium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以33%的产率得到4-[5-[5,5-dimethyl-8-(2-phenylethynyl)-6H-naphthalen-2-yl]-1,2,4-oxadiazol-3-yl]benzoic acid
  参考文献：
  名称：

  Design and synthesis of boron containing potential pan-RAR inverse agonists

  摘要：

  We designed and successfully synthesized the compounds 5 and 8 as potential pan-RAR (retinoic acid receptor) agonists. These two compounds were designed based on an existing pan-RAR agonist (BMS493). We synthesized compound 5, in which the carboxylic acid group in BMS 493 was replaced by boronic ester; and compound 8, in which the double bond of BMS 493 was changed to an oxadiazole (as bioisosteres of double bond) ring. The two target molecules 5 and 8 were synthesized from the commercially available 7-bromo-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-one 1. Compound 1 was derivatized to intermediate 5,5-dimethyl-8-(phenylethynyl)-5,6-dihydronaphthalene-2 carbaldehyde 4 by using alkylation, dehydration, and metal exchange reactions. The intermediate 4 was further converted to 5 by using a Wittig reaction and to 8 by amide coupling and dehydration to give overall 18% and 33% yields, respectively, after 8 steps in each case. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.118
• 作为产物：
  描述：

  在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 叔丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 3.0h， 生成 ethyl 4-(5-(5,5-dimethyl-8-(phenylethynyl)-5,6-dihydronaphthalen-2-yl)-1,2,4-oxadiazol-3-yl)benzoate
  参考文献：
  名称：

  Design and synthesis of boron containing potential pan-RAR inverse agonists

  摘要：

  We designed and successfully synthesized the compounds 5 and 8 as potential pan-RAR (retinoic acid receptor) agonists. These two compounds were designed based on an existing pan-RAR agonist (BMS493). We synthesized compound 5, in which the carboxylic acid group in BMS 493 was replaced by boronic ester; and compound 8, in which the double bond of BMS 493 was changed to an oxadiazole (as bioisosteres of double bond) ring. The two target molecules 5 and 8 were synthesized from the commercially available 7-bromo-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-one 1. Compound 1 was derivatized to intermediate 5,5-dimethyl-8-(phenylethynyl)-5,6-dihydronaphthalene-2 carbaldehyde 4 by using alkylation, dehydration, and metal exchange reactions. The intermediate 4 was further converted to 5 by using a Wittig reaction and to 8 by amide coupling and dehydration to give overall 18% and 33% yields, respectively, after 8 steps in each case. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.118