1-(3H-benzo[f]chromen-2-yl)ethanone

• 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: 1-(3H-benzo[f]chromen-2-yl)ethanone
• 英文别名: 3-acetyl-2H-benzo[f]chromene
• 化学式: C₁₅H₁₂O₂
• 分子量: 224.259
• InChiKey: IDUPZTIMKTYWMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  sodium cyanide 、 1-(3H-benzo[f]chromen-2-yl)ethanone 以 氘代二甲亚砜 、 重水 为溶剂， 生成 (Z)-1-(1-cyano-2-methyl-3-oxobut-1-en-1-yl)naphthalen-2-olate
  参考文献：
  名称：

  Highly selective sensing of cyanide by a benzochromene-based ratiometric fluorescence probe

  摘要：

  Enone-functionalized benzochromene chemodosimeter (1) was prepared through the Baylis-Hillman condensation reaction and was utilized as a ratiometric fluorescence probe for cyanide anions in aqueous buffer. The probe has shown a selective and sensitive response to cyanides over other various anions through the Michael addition and a subsequent [1,3]-sigmatropic rearrangement reaction. When cyanide anions were added, a prominent ratiometric fluorescence change of 1 was observed thus allowing to detect the micromolar concentration of cyanides by the naked eye. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.128
• 作为产物：
  描述：

  丁烯酮 、 2-羟基-1-萘甲醛 在 三乙烯二胺 作用下， 以 氯仿 、 水 为溶剂， 反应 120.0h， 以67%的产率得到1-(3H-benzo[f]chromen-2-yl)ethanone
  参考文献：
  名称：

  A convenient general synthesis of 3-substituted 2H-chromene derivatives

  摘要：

  在Baylis-Hillman条件下，2-羟基苯甲醛和2-羟基-1-萘甲醛与多种活化烯烃反应，显示出区域选择性的环化，生成相应的3-取代色烯衍生物。在某些情况下，观察到烯烃组分的竞争性二聚作用，并且在没有醛的情况下直接二聚也已被探索。

  DOI：

  10.1039/b201827f

文献信息

• A convenient general synthesis of 3-substituted 2H-chromene derivatives
  作者：Perry T Kaye、Xolani W. Nocanda

  DOI：10.1039/b201827f

  日期：2002.5.10

  Reactions of 2-hydroxybenzaldehydes and 2-hydroxy-1-naphthaldehydes with various activated alkenes under Baylis–Hillman conditions have been shown to proceed with regioselective cyclisation to afford the corresponding 3-substituted chromene derivatives. In some cases competitive dimerisation of the alkene component was observed, and direct dimerisation in the absence of the aldehyde has been explored.

  在Baylis-Hillman条件下，2-羟基苯甲醛和2-羟基-1-萘甲醛与多种活化烯烃反应，显示出区域选择性的环化，生成相应的3-取代色烯衍生物。在某些情况下，观察到烯烃组分的竞争性二聚作用，并且在没有醛的情况下直接二聚也已被探索。
• Highly selective sensing of cyanide by a benzochromene-based ratiometric fluorescence probe
  作者：Heejin Lee、Hae-Jo Kim

  DOI：10.1016/j.tetlet.2012.07.128

  日期：2012.10

  Enone-functionalized benzochromene chemodosimeter (1) was prepared through the Baylis-Hillman condensation reaction and was utilized as a ratiometric fluorescence probe for cyanide anions in aqueous buffer. The probe has shown a selective and sensitive response to cyanides over other various anions through the Michael addition and a subsequent [1,3]-sigmatropic rearrangement reaction. When cyanide anions were added, a prominent ratiometric fluorescence change of 1 was observed thus allowing to detect the micromolar concentration of cyanides by the naked eye. (C) 2012 Elsevier Ltd. All rights reserved.