2-(4-nitrobenzoyl)-4,5-methylenedioxyphenylacetone | 433716-67-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-nitrobenzoyl)-4,5-methylenedioxyphenylacetone
• 英文别名: 1-[6-(4-nitrobenzoyl)-1,3-benzodioxol-5-yl]propan-2-one
• CAS: 433716-67-7
• 化学式: C₁₇H₁₃NO₆
• 分子量: 327.293
• InChiKey: AUGHAXCURHVZLX-UHFFFAOYSA-N

物化性质

• 沸点：
  564.9±50.0 °C(Predicted)
• 密度：
  1.380±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-nitrobenzoyl)-4,5-methylenedioxyphenylacetone 在 盐酸 、 sodium tetrahydroborate 、 对甲苯磺酸 、 一水合肼 、 甲基磺酰氯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 28.5h， 生成 3-methyl-6,7-methylenedioxy-1-(4-nitrophenyl)isoquinoline
  参考文献：
  名称：

  Synthesis and antitumor activity of 1,3-benzodioxole derivatives

  摘要：

  A series of 1,3-benzodioxoles (5-19) was synthesized and evaluated for their in vitro antitumor activity against human tumor cell lines. Some derivatives exhibited tumor growth inhibition activity. In particular, 6-(4-aminobenzoyl)-1,3-benzodioxole-5-acetic acid methyl ester 8, the most active compound of the series, possesses a significant growth inhibitory activity on 52 cell lines at concentrations ranging from 10(-7) to 10(-5) M. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01276-4
• 作为产物：
  描述：

  alpha-甲基-1,3-苯并二氧代-5-乙醇 在 phosphorus pentoxide 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 8.0h， 生成 2-(4-nitrobenzoyl)-4,5-methylenedioxyphenylacetone
  参考文献：
  名称：

  A SIMPLE AND EFFICIENT SYNTHESIS OF GYKI 52466 AND GYKI 52895

  摘要：

  The synthesis of 1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine (GYKI 52466. 1), the prototype of a series of noncompetitive AMPA receptor antagonists, and its 3,4-dihydroderivative (GYKI 52895, 2) is described. The title compounds have been prepared starting from safrole through a quite effective procedure.

  DOI：

  10.1081/scc-120002397

文献信息

• Synthesis of 2,3-Benzodiazepines and 2,3-Benzodiazepin-4-ones from Arynes and β-Diketones
  作者：Kentaro Okuma、Yukiko Tanabe、Noriyoshi Nagahora、Kosei Shioji

  DOI：10.1246/bcsj.20150064

  日期：2015.8.15

  2,3-Benzodiazepines were synthesized by two-step or one-pot reactions from aryne precursors. Reaction of 2-(trimethylsilyl)aryl triflates with β-diketones in the presence of CsF gave ortho-substitu...

  2,3-苯二氮卓类化合物是通过芳炔前体的两步或一锅反应合成的。在 CsF 存在下，2-（三甲基甲硅烷基）芳基三氟甲磺酸酯与 β-二酮反应得到邻位取代基...
• One-pot Synthesis of 2,3-Benzodiazepines from Arynes and β-Diketones
  作者：Kentaro Okuma、Yukiko Tanabe、Ryoichi Itoyama、Noriyoshi Nagahora、Kosei Shioji

  DOI：10.1246/cl.130580

  日期：2013.10.5

  Novel one-pot synthesis of 2,3-benzodiazepines from aryne precursors was accomplished. Tofisopam, well-known anxiolytics, could be synthesized via C–C bond insertion of 4,5-dimethoxybenzyne with 2-ethyl-1-(3,4-dimethoxyphenyl)butane-1,3-dione, followed by the reaction with hydrazine hydrate in a one-pot operation. This protocol is applicable to the synthesis of other biologically active 2,3-benzodiazepines, such as Girisopam and Nerisopam.

  成功实现了一锅合成2,3-苯二氮杂烯的小说方法。著名的抗焦虑药托非索潘可以通过4,5-二甲氧基苯乙炔与2-乙基-1-(3,4-二甲氧基苯基)丁烷-1,3-二酮的C–C键插入反应，随后在一锅反应中与水合肼反应来合成。该方法适用于其他生物活性2,3-苯二氮杂烯的合成，如吉利索潘和尼利索潘。
• Synthesis of novel type pyrazolyl and tetrazolyl isoquinolinium zwitterions
  作者：Ibolya Prauda、Jozsef Reiter

  DOI：10.1002/jhet.5570380130

  日期：2001.1

  New type pyrazol-3-yl-isoquinolinium hydrochloride (8a) and tetrazol-5-yl-isoquinolinium (8b) zwitterions were synthesised. Their structures were proved by ir, pmr, cmr, ms spectra as well as X-ray diffraction analysis of model compounds.

  合成了新型吡唑-3-基-异喹啉鎓盐酸盐（8a）和四唑-5-基-异喹啉鎓盐（8b）两性离子。通过ir，pmr，cmr，ms光谱以及模型化合物的X射线衍射分析证明了它们的结构。
• A SIMPLE AND EFFICIENT SYNTHESIS OF GYKI 52466 AND GYKI 52895
  作者：Maria Zappalà、Silvana Grasso、Nicola Micale、Santina Polimeni、Carlo De Micheli

  DOI：10.1081/scc-120002397

  日期：2002.1.1

  The synthesis of 1-(4-aminophenyl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine (GYKI 52466. 1), the prototype of a series of noncompetitive AMPA receptor antagonists, and its 3,4-dihydroderivative (GYKI 52895, 2) is described. The title compounds have been prepared starting from safrole through a quite effective procedure.
• Synthesis and antitumor activity of 1,3-benzodioxole derivatives
  作者：Nicola Micale、Maria Zappalà、Silvana Grasso

  DOI：10.1016/s0014-827x(02)01276-4

  日期：2002.9

  A series of 1,3-benzodioxoles (5-19) was synthesized and evaluated for their in vitro antitumor activity against human tumor cell lines. Some derivatives exhibited tumor growth inhibition activity. In particular, 6-(4-aminobenzoyl)-1,3-benzodioxole-5-acetic acid methyl ester 8, the most active compound of the series, possesses a significant growth inhibitory activity on 52 cell lines at concentrations ranging from 10(-7) to 10(-5) M. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.