(2E,4E)-2,4-dimethyl-5-(6,6,9,9-tetramethyl-4-oxo-6,7,8,9-tetrahydro-4H-benzo[g]chromen-3-yl)penta-2,4-dienoic acid | 1186311-40-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: (2E,4E)-2,4-dimethyl-5-(6,6,9,9-tetramethyl-4-oxo-6,7,8,9-tetrahydro-4H-benzo[g]chromen-3-yl)penta-2,4-dienoic acid
• 英文别名: (2E,4E)-2,4-dimethyl-5-(6,6,9,9-tetramethyl-4-oxo-7,8-dihydrobenzo[g]chromen-3-yl)penta-2,4-dienoic acid
• CAS: 1186311-40-9
• 化学式: C₂₄H₂₈O₄
• 分子量: 380.484
• InChiKey: IPUYNPMRTDZOIS-WEIBIQTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 硫酸 、 溶剂黄146 作用下， 以27%的产率得到(2E,4E)-2,4-dimethyl-5-(6,6,9,9-tetramethyl-4-oxo-6,7,8,9-tetrahydro-4H-benzo[g]chromen-3-yl)penta-2,4-dienoic acid
  参考文献：
  名称：

  Identification of a chromone-based retinoid containing a polyolefinic side chain via facile synthetic routes

  摘要：

  Attempts to prepare substituted chromones as novel retinoids revealed that some chromones were unstable under Wadsworth-Horner-Emmons reaction conditions. Hence, Wittig reactions were used to prepare chromone-based compounds as potential retinoids. Firstly, Wittig reagents prepared from 3-bromomethyl-chromen-4-one were reacted with olefinic-aldehydes to provide the target compounds with all-trans side chains in good yield. The approach supplies a useful general route to structurally diverse chromone-based compounds possessing a variety of side chains. Sequential Wittig reactions were used also to prepare a chromone-based retinoid. These novel compounds were evaluated in binding assays and a high affinity RAR ligand was identified. Crystal structures obtained for two key precursors aided the interpretation of binding data. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.081

文献信息

• Identification of a chromone-based retinoid containing a polyolefinic side chain via facile synthetic routes
  作者：Weilin Sun、Patrick J. Carroll、Dianne R. Soprano、Daniel J. Canney

  DOI：10.1016/j.bmcl.2009.05.081

  日期：2009.8

  Attempts to prepare substituted chromones as novel retinoids revealed that some chromones were unstable under Wadsworth-Horner-Emmons reaction conditions. Hence, Wittig reactions were used to prepare chromone-based compounds as potential retinoids. Firstly, Wittig reagents prepared from 3-bromomethyl-chromen-4-one were reacted with olefinic-aldehydes to provide the target compounds with all-trans side chains in good yield. The approach supplies a useful general route to structurally diverse chromone-based compounds possessing a variety of side chains. Sequential Wittig reactions were used also to prepare a chromone-based retinoid. These novel compounds were evaluated in binding assays and a high affinity RAR ligand was identified. Crystal structures obtained for two key precursors aided the interpretation of binding data. (C) 2009 Elsevier Ltd. All rights reserved.