(E)-2-methyl-3-(6,6,9,9-tetramethyl-4-oxo-6,7,8,9-tetrahydro-4H-benzo[g]chromen-3-yl)acrylaldehyde | 1186311-38-5

• 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: (E)-2-methyl-3-(6,6,9,9-tetramethyl-4-oxo-6,7,8,9-tetrahydro-4H-benzo[g]chromen-3-yl)acrylaldehyde
• 英文别名: (E)-2-methyl-3-(6,6,9,9-tetramethyl-4-oxo-7,8-dihydrobenzo[g]chromen-3-yl)prop-2-enal
• CAS: 1186311-38-5
• 化学式: C₂₁H₂₄O₃
• 分子量: 324.42
• InChiKey: ASFDRZOESSFCFI-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.74
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  47.28
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-2-methyl-3-(6,6,9,9-tetramethyl-4-oxo-6,7,8,9-tetrahydro-4H-benzo[g]chromen-3-yl)acrylaldehyde 、 乙氧甲酰基亚乙基三苯基 以50%的产率得到
  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
• 作为产物：
  描述：

  6,6,9,9-tetramethyl-4-oxo-6,7,8,9-tetrahydro-4H-benzo[g]chromene-3-carbaldehyde 、 2-(三苯基正膦基)丙醛 以 二氯甲烷 为溶剂， 反应 48.0h， 以72%的产率得到(E)-2-methyl-3-(6,6,9,9-tetramethyl-4-oxo-6,7,8,9-tetrahydro-4H-benzo[g]chromen-3-yl)acrylaldehyde
  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