4'-aminoisocaprophenone | 802599-50-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4'-aminoisocaprophenone
• 英文别名: 1-Anilino-4-methyl-pentan-1-on；1-(4-Aminophenyl)-4-methylpentan-1-one
• CAS: 802599-50-4
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: VMFWOQAJMXRKIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4'-aminoisocaprophenone 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 1--4-methyl-pentan-1-ol
  参考文献：
  名称：

  Villa; Ferri; Grana, Farmaco, Edizione Scientifica, 1970, vol. 25, # 2, p. 118 - 124

  摘要：

  DOI：
• 作为产物：
  描述：

  4'-bromoisocaprophenone 在 copper(I) oxide 、 ammonium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 以0.53 g的产率得到4'-aminoisocaprophenone
  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-catalysed transfer hydrogenation of aromatic nitro compounds — an unusual chain elongation
  作者：János Németh、Árpád Kiss、Zoltán Hell

  DOI：10.1016/j.tetlet.2013.08.123

  日期：2013.11

  Aromatic nitro compounds are reduced via transfer hydrogenation in the presence of palladium on magnesium-lanthanum mixed oxide support in ethanol yielding the corresponding amines. With several acetophenone derivatives, the reduction was accompanied by chain elongation whilst the carbonyl group remained intact.

  在钯在乙醇中的镁-镧混合氧化物载体上存在钯时，通过转移氢化还原芳香族硝基化合物，得到相应的胺。对于几种苯乙酮衍生物，还原反应伴随着链延长，而羰基保持完整。
• 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.
• Villa; Ferri; Grana, Farmaco, Edizione Scientifica, 1970, vol. 25, # 2, p. 118 - 124
  作者：Villa、Ferri、Grana、Cattarini Mastelli

  DOI：——

  日期：——