3-methyl-5-[3-(3-methyl-4-nitro-5-isoxazolyl)-2-phenylpropyl]-4-nitroisoxazole | 496806-21-4

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 3-methyl-5-[3-(3-methyl-4-nitro-5-isoxazolyl)-2-phenylpropyl]-4-nitroisoxazole
• 英文别名: 2-phenyl-1,3-di(3-methyl-4-nitroisoxazol-5-yl)propane；3-Methyl-5-[3-(3-methyl-4-nitro-1,2-oxazol-5-yl)-2-phenylpropyl]-4-nitro-1,2-oxazole
• CAS: 496806-21-4
• 化学式: C₁₇H₁₆N₄O₆
• 分子量: 372.337
• InChiKey: LWHBHKAZDPURSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-methyl-5-[3-(3-methyl-4-nitro-5-isoxazolyl)-2-phenylpropyl]-4-nitroisoxazole 在 potassium permanganate 作用下， 以 水 、 丙酮 为溶剂， 以71%的产率得到3-苯基戊二酸
  参考文献：
  名称：

  Three multicomponent reactions of 3,5-dimethyl-4-nitroisoxazole

  摘要：

  The title compound is used to prepare 3-arylglutaric acids, bis-isoxazoles and bis-pyrazoles from commercially available materials. The methodologies described have afforded important synthetic intermediates in high yields and without the use of chromatography. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.015
• 作为产物：
  描述：

  3,5-二甲基-4-硝基异噁唑 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 1.5h， 生成 3-methyl-5-[3-(3-methyl-4-nitro-5-isoxazolyl)-2-phenylpropyl]-4-nitroisoxazole
  参考文献：
  名称：

  Multi-component synthesis and in vitro and in vivo anticancer activity of novel arylmethylene bis-isoxazolo[4,5-b]pyridine-N-oxides

  摘要：

  A three component one-pot protocol has been investigated for the synthesis of arylmethylene bis-isoxazolo[4,5-b]pyridine-N-oxides 1 from the commercially available materials. The title compounds 1 were also synthesized by a step-wise method and found to be identical with one-pot synthesis by spectral and analytical data. The newly synthesized compounds were evaluated for their in vitro anticancer activity against human cancer cell lines and in vivo anticancer activity on EAC-bearing mice. Compound 1a was found to be the most active both in in vitro and in vivo cytotoxic studies. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.004

文献信息

• Synthesis and in vitro and in vivo anticancer activity of novel phenylmethylene bis-isoxazolo[4,5-b]azepines
  作者：E. Rajanarendar、M. Nagi Reddy、K. Rama Murthy、P. Surendar、R.N. Reddy、Y.N. Reddy

  DOI：10.1016/j.bmcl.2011.11.044

  日期：2012.1

  piperidine afforded the Michael type adducts 8, which on treatment with different substituted chalcones in the presence of piperidine gave the Michael adducts 9. Compounds 9 underwent reductive cyclization on treatment with SnCl2–MeOH to afford the title compounds 10. Structure of these compounds was established on the basis of IR, 1H NMR, 13C NMR and Mass spectral data. The title compounds 10a–j were evaluated

  从3-甲基-4-硝基-5-苯乙烯基恶唑6合成了一系列新型的苯基亚甲基双-异恶唑并[4,5- b ] a庚因衍生物（10）。的反应6与3,5-二甲基-4- nitroisoxazole（7在哌啶，得到迈克尔加成物型）8，其用在哌啶的存在下不同的取代的查耳酮处理，得到的迈克尔加合物9。化合物9经过SnCl 2 -MeOH处理后进行还原环化，得到标题化合物10。这些化合物的结构是根据IR，1 H NMR，13 C NMR和质谱数据。评价了标题化合物10a – j的体外和体内抗癌活性。与标准药物顺铂相比，化合物10j具有良好的抗癌活性。
• A Fast and Highly Efficient Protocol for Synthesis of Pyrrolo[2,3-d]isoxazoles and a New Series of Novel Benzyl Bis-pyrrolo[2,3-d]isoxazoles Using Task-Specific Ionic Liquids as Catalyst and Green Solvent
  作者：Eligeti Rajanarendar、Samala Raju、Atthunuri Siva Rami Reddy、Kundur Govardhan Reddy、Modugu Nagi Reddy

  DOI：10.1248/cpb.58.833

  日期：——

  We report a mild, fast, highly efficient and eco-friendly protocol for the green synthesis of pyrrolo[2,3-d]isoxazoles and a new series of novel benzyl bis-pyrrolo[2,3-d]isoxazoles from nitro styrylisoxazoles in SnCl(2)-ionic liquid by reductive cyclization. These reactions were performed at ambient temperature which resulted in good yields in short reaction time, without requiring any organic solvent

  我们报告了一种温和，快速，高效和环保的方案，用于从硝基硝基苯乙烯基恶唑中合成吡咯并[2,3-d]异恶唑和一系列新的新型苄基双吡咯并[2,3-d]异恶唑。 SnCl（2）离子液体的还原环化。这些反应在环境温度下进行，从而在短的反应时间内获得了良好的产率，而无需任何有机溶剂和催化剂。
• Three multicomponent reactions of 3,5-dimethyl-4-nitroisoxazole
  作者：Mauro F.A. Adamo、Vivekananda R. Konda、Donato Donati、Piero Sarti-Fantoni、Tomas Torroba

  DOI：10.1016/j.tet.2007.07.015

  日期：2007.9

  The title compound is used to prepare 3-arylglutaric acids, bis-isoxazoles and bis-pyrazoles from commercially available materials. The methodologies described have afforded important synthetic intermediates in high yields and without the use of chromatography. (c) 2007 Elsevier Ltd. All rights reserved.
• Multi-component synthesis and in vitro and in vivo anticancer activity of novel arylmethylene bis-isoxazolo[4,5-b]pyridine-N-oxides
  作者：E. Rajanarendar、S. Raju、M. Nagi Reddy、S. Rama Krishna、L. Hari Kiran、A. Ram Narasimha Reddy、Y. Narasimha Reddy

  DOI：10.1016/j.ejmech.2012.02.004

  日期：2012.4

  A three component one-pot protocol has been investigated for the synthesis of arylmethylene bis-isoxazolo[4,5-b]pyridine-N-oxides 1 from the commercially available materials. The title compounds 1 were also synthesized by a step-wise method and found to be identical with one-pot synthesis by spectral and analytical data. The newly synthesized compounds were evaluated for their in vitro anticancer activity against human cancer cell lines and in vivo anticancer activity on EAC-bearing mice. Compound 1a was found to be the most active both in in vitro and in vivo cytotoxic studies. (C) 2012 Elsevier Masson SAS. All rights reserved.