4'-aminoisovalerophenone | 121198-77-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4'-aminoisovalerophenone
• 英文别名: 1-(4-amino-phenyl)-3-methyl-butan-1-one；1-(4-Amino-phenyl)-3-methyl-butan-1-on；1-(4-Aminophenyl)-3-methylbutan-1-one
• CAS: 121198-77-4
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: ASZLECJXVTVBBY-UHFFFAOYSA-N

物化性质

• 沸点：
  323.7±15.0 °C(Predicted)
• 密度：
  1.023±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  1-(4-bromophenyl)-3-methylbutan-1-one 在 copper(I) oxide 、 ammonium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 以0.72 g的产率得到4'-aminoisovalerophenone
  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

• Palladium-Catalyzed Reaction of Acyliron Complexes with Aryl Halides. A Convenient Synthesis of Aromatic Ketones
  作者：Teruyoshi Koga、Shinako Makinouchi、Nobuhisa Okukado

  DOI：10.1246/cl.1988.1141

  日期：1988.7.5

  Acyliron complexes, easily prepared from disodium tetracarbonylferrate and alkyl halides, reacted with aryl iodides in the presence of a catalytic amount of Pd(PPh3)4 and a cocatalyst, ZnCl2, to give aromatic ketones in good yields. (R)-2-Methyl-1-phenyl-1-octanone was prepared starting from (S)-2-bromooctane in an excellent optical yield.

  在催化量的 Pd(PPh3)4 和助催化剂 ZnCl2 存在下，丙烯酰络合物很容易由四羰基铁酸二钠和烷基卤化物制备，与芳基碘反应，以良好的收率得到芳族酮。(R)-2-甲基-1-苯基-1-辛酮是从 (S)-2-溴辛烷以优异的光学产率制备的。
• DE715930
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.

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