5-[(E)-2-(2-Methoxy-phenyl)-vinyl]-3-methyl-4-nitro-isoxazole | 74917-83-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-[(E)-2-(2-Methoxy-phenyl)-vinyl]-3-methyl-4-nitro-isoxazole
• 英文别名: 5-[2-(2-Methoxyphenyl)ethenyl]-3-methyl-4-nitro-1,2-oxazole
• CAS: 74917-83-2
• 化学式: C₁₃H₁₂N₂O₄
• 分子量: 260.249
• InChiKey: QRDFNIVYTDSVQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  81.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[(E)-2-(2-Methoxy-phenyl)-vinyl]-3-methyl-4-nitro-isoxazole 在 盐酸 、 tin 作用下， 以47%的产率得到5-[(E)-2-(2-Methoxy-phenyl)-vinyl]-3-methyl-isoxazol-4-ylamine
  参考文献：
  名称：

  Martinez, R.; Cortes, E., Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 185 - 187

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-二甲基-4-硝基异噁唑 、 邻甲氧基苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 生成 5-[(E)-2-(2-Methoxy-phenyl)-vinyl]-3-methyl-4-nitro-isoxazole
  参考文献：
  名称：

  膦催化的[3 + 2]森田-贝利斯-希尔曼碳酸盐与异恶唑基烯烃的环化

  摘要：

  已开发出一种膦催化的森田-贝利斯-希尔曼（MBH）碳酸酯与3-甲基-4-硝基-5-苯乙烯基恶唑的碳酸盐环化反应[3 + 2]，以中等至良好的产率提供各种多功能异恶唑，具有中等至优异的非对映选择性。用螺环手性膦作为催化剂，获得高达89％的ee。

  DOI：

  10.1021/acs.joc.0c01948

文献信息

• The highly chemoselective transfer hydrogenation of the carbon–carbon double bond of conjugated nitroalkenes by a rhodium complex
  作者：Jing Xiang、Er-Xiao Sun、Chun-Xia Lian、Wei-Cheng Yuan、Jin Zhu、Qiwei Wang、Jingen Deng

  DOI：10.1016/j.tet.2012.04.028

  日期：2012.6

  Chemoselective transfer hydrogenation of conjugated nitroalkenes catalyzed by [RhCl2Cp∗]2–diamine complex (Cp∗=η5-C5Me5) using HCOOH/Et3N (5:2) (TEAF) as a hydrogen source was realized. A variety of nitrostyrenes, β-methyl nitrostyrenes, and 3-methyl-4-nitro-5-alkenyl-isoxazoles were reduced smoothly in good to excellent yields in short reaction time. Other functional groups are inert under the reaction

  通过[催化的RhCl缀合的硝基烯烃化学选择性转移氢化2的Cp * ] 2 -二胺复合物（CP * =η 5 -C 5我5）使用HCOOH / ET 3 N（5：2）（TEAF）作为氢源，实现。各种硝基苯乙烯，β-甲基硝基苯乙烯和3-甲基-4-硝基-5-链烯基-异恶唑均能在短时间内以良好或极好的收率顺利还原。在反应条件下，其他官能团是惰性的。
• Water-mediated and promoted eco-friendly one-pot synthesis of azaarene substituted isoxazoles
  作者：Dharavath Nagaraju、Eligeti Rajanarendar、Pittala Praveen Kumar、Modugu Nagi Reddy

  DOI：10.1039/c7nj01165b

  日期：——

  to be good CC electrophilic acceptors for the construction of various azaarene-containing Michael addition products. This method provides an efficient and environmentally benign method for the one-pot synthesis of biologically important azaarene-substituted isoxazole derivatives in good yields. The important aspects of the present methodology are the use of non-toxic solvent, that it is catalyst free

  已经描述了一种有效的绿色方法，用于在水中将2-甲基氮杂芳烃的sp 3 C–H键官能化为3-甲基-4-硝基-5-苯乙烯基恶唑。硝基苯乙烯基恶唑被证明是用于构建各种含氮杂芳烃的迈克尔加成产物的良好C C亲电受体。该方法提供了一种有效且对环境有益的方法，可以高收率一锅合成生物学上重要的氮杂芳烃取代的异恶唑衍生物。本方法学的重要方面是使用无毒溶剂，无催化剂，易于纯化和较大的底物范围。
• 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.
• Phosphine-Catalyzed [3 + 2] Annulation of Morita–Baylis–Hillman Carbonates with Isoxazole-Based Alkenes
  作者：Jianning Liao、Jipan Dong、Jiaqing Xu、Wei Wang、Yongjun Wu、Yuxia Hou、Hongchao Guo

  DOI：10.1021/acs.joc.0c01948

  日期：2021.2.5

  A phosphine-catalyzed [3 + 2] annulation of Morita–Baylis–Hillman (MBH) carbonates with 3-methyl-4-nitro-5-styrylisoxazoles has been developed to afford various multifunctional isoxazoles in moderate to good yields with moderate to excellent diastereoselectivities. With a spirocyclic chiral phosphine as the catalyst, up to 89% ee was obtained.

  已开发出一种膦催化的森田-贝利斯-希尔曼（MBH）碳酸酯与3-甲基-4-硝基-5-苯乙烯基恶唑的碳酸盐环化反应[3 + 2]，以中等至良好的产率提供各种多功能异恶唑，具有中等至优异的非对映选择性。用螺环手性膦作为催化剂，获得高达89％的ee。
• Martinez, R.; Cortes, E., Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 185 - 187
  作者：Martinez, R.、Cortes, E.

  DOI：——

  日期：——