4'-bromo-2-methylbutyrophenone | 64686-75-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4'-bromo-2-methylbutyrophenone
• 英文别名: 1-(4-bromophenyl)-2-methylbutan-1-one；(S)-2-Methyl-4'-brombutyrophenon
• CAS: 64686-75-5
• 化学式: C₁₁H₁₃BrO
• 分子量: 241.128
• InChiKey: JALIPXXESLYLMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4'-bromo-2-methylbutyrophenone 在 copper(I) oxide 、 ammonium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 以30 mg的产率得到4'-amino-2-methylbutyrophenone
  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
• 作为产物：
  描述：

  4-溴苯甲酸 在 [Ir(dF(CF₃)ppy)₂(dtbbpy)](PF₆) 、 C₆H₁₀N₃⁽¹⁺⁾*BF₄^(1-) 、 caesium carbonate 、 triethylamine tris(hydrogen fluoride) 、 ethanaminium,N-(difluoro-λ⁴-sulfanylidene)-N-ethyl-,tetrafluoroborate 作用下， 以 二氯甲烷 、 乙酸甲酯 为溶剂， 反应 7.0h， 生成 4'-bromo-2-methylbutyrophenone
  参考文献：
  名称：

  光氧化还原和 N-杂环卡宾协同催化 Suzuki-Miyaura 型反应：芳酰氟和烷基硼酸的自由基偶联

  摘要：

  通过协同N-杂环卡宾 (NHC) 和光氧化还原催化，揭示了苯甲酰氟与烷基硼酸合成酮的分子间 Suzuki-Miyaura 型反应。各种烷基硼酸无需外部氧化剂或活化剂即可转化为烷基自由基。此外，该催化体系可通过自由基中继过程实现苯乙烯的双官能化。机理实验表明苯甲酸阴离子中间体可能在该反应体系中发挥独特的作用。

  DOI：

  10.1021/acs.orglett.4c00334

文献信息

• Desai,A.P. et al., Journal of the Indian Chemical Society, 1970, vol. 47, p. 117 - 118
  作者：Desai,A.P. et al.

  DOI：——

  日期：——
• 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.
• Cooperative Photoredox and <i>N</i>-Heterocyclic Carbene Catalysis Suzuki–Miyaura-Type Reaction: Radical Coupling of Aroyl Fluorides and Alkyl Boronic Acids
  作者：Shihao Li、Chaoyang Zhang、Sheng Wang、Wenqing Yang、Xinru Fang、Shilu Fan、Qi Zhang、Xiao-Xuan Li、Yi-Si Feng

  DOI：10.1021/acs.orglett.4c00334

  日期：2024.3.1

  Suzuki–Miyaura-type reaction of benzoyl fluorides with alkyl boronic acids to synthetic ketone was revealed by cooperative N-heterocyclic carbene (NHC) and photoredox catalysis. Various alkyl boric acids can be converted into alkyl radicals without external oxidants or activators. Moreover, the catalytic system was feasible for the difunctionalization of styrenes via a radical relay process. Mechanistic

  通过协同N-杂环卡宾 (NHC) 和光氧化还原催化，揭示了苯甲酰氟与烷基硼酸合成酮的分子间 Suzuki-Miyaura 型反应。各种烷基硼酸无需外部氧化剂或活化剂即可转化为烷基自由基。此外，该催化体系可通过自由基中继过程实现苯乙烯的双官能化。机理实验表明苯甲酸阴离子中间体可能在该反应体系中发挥独特的作用。