4-aminophenyl cyclobutyl ketone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-aminophenyl cyclobutyl ketone
• 英文别名: 4-Cyclobutanecarbonylaniline；(4-aminophenyl)-cyclobutylmethanone
• 化学式: C₁₁H₁₃NO
• mdl: MFCD19673477
• 分子量: 175.23
• InChiKey: LXTHVGZRVLIZPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (4-溴苯基)(环丁基)甲酮 在 copper(I) oxide 、 ammonium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 以0.10 g的产率得到4-aminophenyl cyclobutyl ketone
  参考文献：
  名称：

  Synthesis and methemoglobinemia-inducing properties of analogues of para-aminopropiophenone designed as humane rodenticides

  摘要：

  A number of structural analogues of the known toxicant para-aminopropiophenone (PAPP) have been prepared and evaluated for their capacity to induce methemoglobinemia-with a view to their possible application as humane pest control agents. It was found that an optimal lipophilicity for the formation of methemoglobin (metHb) in vitro existed for alkyl analogues of PAPP (aminophenones 1-20; compound 6 metHb% = 74.1 +/- 2). Besides lipophilicity, this structural sub-class suggested there were certain structural requirements for activity, with both branched (10-16) and cyclic (17-20) alkyl analogues exhibiting inferior in vitro metHb induction. Of the four candidates (compounds 4, 6, 13 and 23) evaluated in vivo, 4 exhibited the greatest toxicity. In parallel, aminophenone bioisosteres, including oximes 30-32, sulfoxide 33, sulfone 34 and sulfonamides 35-36, were found to be inferior metHb inducers to lead ketone 4. Closer examination of Hammett substituent constants suggests that a particular combination of the field and resonance parameters may be significant with respect to the redox mechanisms behind PAPPs metHb toxicity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.046

文献信息

• Direct preparation of new organozinc reagents, aminophenylzinc iodides, and their applications
  作者：Hye-Soo Jung、Seung-Hoi Kim

  DOI：10.1016/j.tetlet.2015.01.053

  日期：2015.2

  New organozinc reagents, 4-aminophenyl zinc iodide (A) and 3-aminophenyl zinc iodide (B), have been generated easily and effectively by the direct insertion of active zinc to iodoanilines which possess acidic protons. The subsequent coupling reactions of the organozincs with various acid chlorides turned out to be an efficient tool for the preparation of aminophenyl ketones.

  通过将活性锌直接插入具有酸性质子的碘代苯胺中，可以轻松而有效地产生新的有机锌试剂，即4-氨基苯基碘化锌（A）和3-氨基苯基碘化锌（B）。后来有机锌与各种酰氯的偶合反应被证明是制备氨基苯基酮的有效工具。
• Synthesis and methemoglobinemia-inducing properties of analogues of para-aminopropiophenone designed as humane rodenticides
  作者：David Rennison、Daniel Conole、Malcolm D. Tingle、Junpeng Yang、Charles T. Eason、Margaret A. Brimble

  DOI：10.1016/j.bmcl.2013.10.046

  日期：2013.12

  A number of structural analogues of the known toxicant para-aminopropiophenone (PAPP) have been prepared and evaluated for their capacity to induce methemoglobinemia-with a view to their possible application as humane pest control agents. It was found that an optimal lipophilicity for the formation of methemoglobin (metHb) in vitro existed for alkyl analogues of PAPP (aminophenones 1-20; compound 6 metHb% = 74.1 +/- 2). Besides lipophilicity, this structural sub-class suggested there were certain structural requirements for activity, with both branched (10-16) and cyclic (17-20) alkyl analogues exhibiting inferior in vitro metHb induction. Of the four candidates (compounds 4, 6, 13 and 23) evaluated in vivo, 4 exhibited the greatest toxicity. In parallel, aminophenone bioisosteres, including oximes 30-32, sulfoxide 33, sulfone 34 and sulfonamides 35-36, were found to be inferior metHb inducers to lead ketone 4. Closer examination of Hammett substituent constants suggests that a particular combination of the field and resonance parameters may be significant with respect to the redox mechanisms behind PAPPs metHb toxicity. (C) 2013 Elsevier Ltd. All rights reserved.