2-(2-acetylphenoxy)-1-iodoethane | 850895-58-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-acetylphenoxy)-1-iodoethane
• 英文别名: 2-(2-iodoethoxy)acetophenone；1-[2-(2-Iodoethoxy)phenyl]ethanone
• CAS: 850895-58-8
• 化学式: C₁₀H₁₁IO₂
• 分子量: 290.101
• InChiKey: NYPKFYJUQFQBCP-UHFFFAOYSA-N

物化性质

• 沸点：
  332.8±22.0 °C(Predicted)
• 密度：
  1.608±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  2-(2-acetylphenoxy)-1-iodoethane 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 48.0h， 生成 (2R)-2-[((2-(2-acetylphenoxy)ethyl)-amino)methyl]-1,4-benzodioxane
  参考文献：
  名称：

  QSAR study for a novel series of ortho monosubstituted phenoxy analogues of α1-adrenoceptor antagonist WB4101

  摘要：

  A number of (S)- and (R)-2-[(2-phenoxyethyl)aminomethyl]-1,4-benzodioxanes unsubstituted or ortho monosubstituted at the phenoxy moiety were synthesized and tested in binding assays on the alpha(1a)-AR, alpha(1b)-AR alpha(1d)-AR and the 5-HT1A receptor. The affinity values of the new compounds 1-16 were compared with those of the enantiomers of the 2,6-dimethoxyphenoxy analogue, the well-known alpha(1) antagonist WB4101, finding that the unsubstituted derivative (S)-1 and the o-methyl, the o-t-butyl, the o-fluoro and the o-methoxy derivatives, (S)-2, (S)-4, (S)-8 and (S)-16, respectively, display a significantly specific 5-HT1A affinity, very close, with the exception of (S)-4, to the almost nanomolar one of (S)-WB4101. Otherwise sensible affinity decreases were recorded for the three alpha(1)-AR subtypes. A classical quantitative structure-activity relationship (Hansch) analysis was successfully applied to compounds (S)-1 to (S)-16 and (S)-WB4101 to rationalize such binding data. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.01.034
• 作为产物：
  描述：

  2-(2-acetylphenoxy)ethanol 在 吡啶 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 12.0h， 生成 2-(2-acetylphenoxy)-1-iodoethane
  参考文献：
  名称：

  QSAR study for a novel series of ortho monosubstituted phenoxy analogues of α1-adrenoceptor antagonist WB4101

  摘要：

  A number of (S)- and (R)-2-[(2-phenoxyethyl)aminomethyl]-1,4-benzodioxanes unsubstituted or ortho monosubstituted at the phenoxy moiety were synthesized and tested in binding assays on the alpha(1a)-AR, alpha(1b)-AR alpha(1d)-AR and the 5-HT1A receptor. The affinity values of the new compounds 1-16 were compared with those of the enantiomers of the 2,6-dimethoxyphenoxy analogue, the well-known alpha(1) antagonist WB4101, finding that the unsubstituted derivative (S)-1 and the o-methyl, the o-t-butyl, the o-fluoro and the o-methoxy derivatives, (S)-2, (S)-4, (S)-8 and (S)-16, respectively, display a significantly specific 5-HT1A affinity, very close, with the exception of (S)-4, to the almost nanomolar one of (S)-WB4101. Otherwise sensible affinity decreases were recorded for the three alpha(1)-AR subtypes. A classical quantitative structure-activity relationship (Hansch) analysis was successfully applied to compounds (S)-1 to (S)-16 and (S)-WB4101 to rationalize such binding data. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.01.034