1-(m-nitrophenyl)-3-(p-methylphenyl)propan-1,3-dione | 57026-79-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(m-nitrophenyl)-3-(p-methylphenyl)propan-1,3-dione
• 英文别名: 1-(3-nitrophenyl)(p-tolyl)propane-1,3-dione；1-(4-Methylphenyl)-3-(3-nitrophenyl)propane-1,3-dione
• CAS: 57026-79-6
• 化学式: C₁₆H₁₃NO₄
• 分子量: 283.284
• InChiKey: SLOAQKWHOIAJDO-UHFFFAOYSA-N

物化性质

• 沸点：
  450.3±30.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(m-nitrophenyl)-3-(p-methylphenyl)propan-1,3-dione 在 盐酸 、 palladium on activated charcoal 、 氢气 、 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 17.0h， 生成 C₂₄H₁₉F₃N₄O
  参考文献：
  名称：

  Design, synthesis, and in vitro evaluation of N-(3-(3-alkyl-1H-pyrazol-5-yl) phenyl)-aryl amide for selective RAF inhibition

  摘要：

  Notorious oncogenic BRAF V600E plays a significant role in the signal transduction of the MAPK pathway, which is involved in tumor growth, especially in melanoma. Much effort has been made to suppress BRAF V600E through small molecules like vemurafenib and dabrafenib, but the MAPK pathway remains active through paradoxical activation, where CRAF transmits the signal of the MAPK pathway either alone or along with BRAF V600E. Therefore, we designed and synthesized a new series of N-(3-(3-alkyl-1H-pyrazol-5-yl) phenyl)-aryl amide/urea analogues that showed potent inhibitory activities against BRAF V600E and CRAF. Compound 7c exhibited particularly superior selectivity toward BRAF V600E and CRAF over 30 other protein kinases, implying that this chemotype could be investigated as a BRAF paradox breaker. (C) 2019 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2019.01.003
• 作为产物：
  描述：

  4-甲基苯丙酮 在 氢氧化钾 、 sodium hydroxide 、 溴 作用下， 以 甲醇 、 乙醇 、 氯仿 为溶剂， 反应 6.0h， 生成 1-(m-nitrophenyl)-3-(p-methylphenyl)propan-1,3-dione
  参考文献：
  名称：

  Has, Chandra; Saharia; Sharma, Journal of the Indian Chemical Society, 1996, vol. 73, # 11, p. 614 - 615

  摘要：

  DOI：

文献信息

• Rhodium-Catalyzed Aerobic Decomposition of 1,3-Diaryl-2-diazo-1,3-diketones: Mechanistic Investigation and Application to the Synthesis of Benzils
  作者：Jia-Liang Zhu、Yi-Ting Tsai

  DOI：10.1021/acs.joc.0c02366

  日期：2021.1.1

  proceed via the interaction of a ketene intermediate resulting from a Wolff rearrangement of the carbenoid, with a rhodium peroxide or peroxy radical species generated upon the activation of molecular oxygen. The proposed mechanism has been supported by the results from a set of controlled experiments. By using this newly developed strategy, a large array of benzil derivatives as well as 9,10-phenanthrenequinone

  基于铑（II）催化的需氧分解过程，报道了1,3-二芳基-2-重氮-1,3-二酮向1,2-二芳基-1,2-二酮（苯）的转化。该反应在环境温度下发生，并且可以在氧气的气球压力下由少量羧酸的铑（5mol％）催化。此外，显示出来自O 2试剂的氧原子被掺入产物中，并且这伴随着羰基单元从起始原料的挤出。从机理上讲，建议分解可以通过类胡萝卜素的沃尔夫重排产生的乙烯酮中间体与分子氧活化后产生的过氧化铑或过氧自由基的相互作用。一组受控实验的结果支持了所提出的机制。通过使用这种新开发的策略，从相应的重氮底物以不同的收率合成了大量苯并衍生物和9,10-菲醌。另一方面，由于难以诱导初始重排，该方法不能从2-重氮-1，3-茚满二酮生成苯并环丁烯-1,2-二酮。
• Design, synthesis, and in vitro evaluation of N-(3-(3-alkyl-1H-pyrazol-5-yl) phenyl)-aryl amide for selective RAF inhibition
  作者：Hoyong Jung、Jinwoong Kim、Daseul Im、Hyungwoo Moon、Jung-Mi Hah

  DOI：10.1016/j.bmcl.2019.01.003

  日期：2019.2

  Notorious oncogenic BRAF V600E plays a significant role in the signal transduction of the MAPK pathway, which is involved in tumor growth, especially in melanoma. Much effort has been made to suppress BRAF V600E through small molecules like vemurafenib and dabrafenib, but the MAPK pathway remains active through paradoxical activation, where CRAF transmits the signal of the MAPK pathway either alone or along with BRAF V600E. Therefore, we designed and synthesized a new series of N-(3-(3-alkyl-1H-pyrazol-5-yl) phenyl)-aryl amide/urea analogues that showed potent inhibitory activities against BRAF V600E and CRAF. Compound 7c exhibited particularly superior selectivity toward BRAF V600E and CRAF over 30 other protein kinases, implying that this chemotype could be investigated as a BRAF paradox breaker. (C) 2019 Elsevier Ltd. All rights reserved.
• Has, Chandra; Saharia; Sharma, Journal of the Indian Chemical Society, 1996, vol. 73, # 11, p. 614 - 615
  作者：Has, Chandra、Saharia、Sharma、Sharma

  DOI：——

  日期：——