2-(2,3-dihydro-3,3-dimethyl-5-benzofuranyl)-3-buten-2-ol | 213972-14-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 2-(2,3-dihydro-3,3-dimethyl-5-benzofuranyl)-3-buten-2-ol
• 英文别名: 2-(3,3-dimethyl-2H-1-benzofuran-5-yl)but-3-en-2-ol
• CAS: 213972-14-6
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: CPTXTEZMKLFSOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2,3-dihydro-3,3-dimethyl-5-benzofuranyl)-3-buten-2-ol 在 正丁基锂 作用下， 以 甲醇 为溶剂， 反应 66.25h， 生成
  参考文献：
  名称：

  Synthesis and Characterization of Heteroarotinoids Demonstrate Structure Specificity Relationships

  摘要：

  Heteroarotinoids are synthetic retinoids derived from trans-retinoic acid and the arotinoid structures and include a heteroatom in a five- or six-membered cyclic ring. This is the first systematic study of influences of the heteroatom, ring size, number of aryl groups, and terminal side chain on retinoid receptor specificity. Two new heteroarotinoids were synthesized and characterized. Although all heteroarotinoids activated RAR receptors, two dominant associations between structure and specificity were identified across all compounds. The six-membered ring conferred increased RAR beta specificity over the five-membered ring. The sulfur atom conferred greater specificity for RAR gamma than the oxygen atom. RAR alpha specificity was attenuated by a combination of influences from the heteroatom and aryl groups. In summary, the heteroatom and cyclic ring size exerted dominant effects, while the number of aryl rings and terminal side chain had attenuating effects on retinoid receptor specificity of heteroarotinoids.

  DOI：

  10.1021/jm980308p
• 作为产物：
  描述：

  以 四氢呋喃 为溶剂， 反应 7.5h， 生成 2-(2,3-dihydro-3,3-dimethyl-5-benzofuranyl)-3-buten-2-ol
  参考文献：
  名称：

  Synthesis and Characterization of Heteroarotinoids Demonstrate Structure Specificity Relationships

  摘要：

  Heteroarotinoids are synthetic retinoids derived from trans-retinoic acid and the arotinoid structures and include a heteroatom in a five- or six-membered cyclic ring. This is the first systematic study of influences of the heteroatom, ring size, number of aryl groups, and terminal side chain on retinoid receptor specificity. Two new heteroarotinoids were synthesized and characterized. Although all heteroarotinoids activated RAR receptors, two dominant associations between structure and specificity were identified across all compounds. The six-membered ring conferred increased RAR beta specificity over the five-membered ring. The sulfur atom conferred greater specificity for RAR gamma than the oxygen atom. RAR alpha specificity was attenuated by a combination of influences from the heteroatom and aryl groups. In summary, the heteroatom and cyclic ring size exerted dominant effects, while the number of aryl rings and terminal side chain had attenuating effects on retinoid receptor specificity of heteroarotinoids.

  DOI：

  10.1021/jm980308p

文献信息

• Synthesis and Characterization of Heteroarotinoids Demonstrate Structure Specificity Relationships
  作者：Doris M. Benbrook、Shankar Subramanian、Jonathan B. Gale、Shengquan Liu、Chad W. Brown、Marcus F. Boehm、K. Darrell Berlin

  DOI：10.1021/jm980308p

  日期：1998.9.1

  Heteroarotinoids are synthetic retinoids derived from trans-retinoic acid and the arotinoid structures and include a heteroatom in a five- or six-membered cyclic ring. This is the first systematic study of influences of the heteroatom, ring size, number of aryl groups, and terminal side chain on retinoid receptor specificity. Two new heteroarotinoids were synthesized and characterized. Although all heteroarotinoids activated RAR receptors, two dominant associations between structure and specificity were identified across all compounds. The six-membered ring conferred increased RAR beta specificity over the five-membered ring. The sulfur atom conferred greater specificity for RAR gamma than the oxygen atom. RAR alpha specificity was attenuated by a combination of influences from the heteroatom and aryl groups. In summary, the heteroatom and cyclic ring size exerted dominant effects, while the number of aryl rings and terminal side chain had attenuating effects on retinoid receptor specificity of heteroarotinoids.