[2-nitro-3-(2-nitrophenyl)prop-2-enyl] acetate | 114430-08-9

• 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-nitro-3-(2-nitrophenyl)prop-2-enyl] acetate
• CAS: 114430-08-9
• 化学式: C₁₁H₁₀N₂O₆
• 分子量: 266.21
• InChiKey: YRYIOHOQYJSJOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  112.58
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  [2-nitro-3-(2-nitrophenyl)prop-2-enyl] acetate 、 邻氨基二苯胺 以 甲醇 为溶剂， 反应 3.0h， 以71%的产率得到(E)-N1-(2-nitro-3-(2-nitrophenyl)allyl)-N2-phenylbenzene-1,2-diamine
  参考文献：
  名称：

  Base and catalyst-free synthesis of nitrobenzodiazepines via a cascade N-nitroallylation-intramolecular aza-Michael addition involving o-phenylenediamines and nitroallylic acetates

  摘要：

  DOI：

  10.1016/j.tet.2019.130761

文献信息

• Naphthoquinone-based chalcone hybrids and derivatives: synthesis and potent activity against cancer cell lines
  作者：Guilherme A. M. Jardim、Tiago T. Guimarães、Maria do Carmo F. R. Pinto、Bruno C. Cavalcanti、Kaio M. de Farias、Claudia Pessoa、Claudia C. Gatto、Divya K. Nair、Irishi N. N. Namboothiri、Eufrânio N. da Silva Júnior

  DOI：10.1039/c4md00371c

  日期：——

  Naphthoquinone-based chalcone hybrids were synthesized and evaluated for their cytotoxic activity against four cancer cell lines and PBMC. Some of the hybrids exhibited promising anticancer activity with IC₅₀ values < 1 μM.

  基于萘醌的查尔酮杂合物被合成并对其对四种癌细胞系和PBMC的细胞毒活性进行了评估。其中一些杂合物表现出有前景的抗癌活性，IC₅₀值小于1μM。
• Asymmetric synthesis of pyrano[2,3-c]pyrazoles via a cascade reaction between Morita–Baylis–Hillman acetates of nitroalkenes and pyrazolones
  作者：Jin Xie、Feng Sha、Xin-Yan Wu

  DOI：10.1016/j.tet.2016.05.033

  日期：2016.7

  The first organocatalytic enantioselective cascade reaction of Morita–Baylis–Hillman acetates of nitroalkenes with pyrazolones has been developed. With 20 mol % of chiral tertiary-amine squaramide, 1,4,5,6-tetrahydropyrano[2,3-c]pyrazoles were afforded in moderate yields (up to 71%) with excellent stereoselectivities (up to>99:1 dr and up to 98% ee).

  已经开发出Morita-Baylis-Hillman的硝基烯烃乙酸酯与吡唑啉酮的第一个有机催化对映选择性级联反应。有了20 mol％的手性叔胺方酸酰胺，就可以以中等收率（高达71％）提供1,4,5,6-四氢吡喃并[2,3-c]吡唑类化合物，且具有优异的立体选择性（高达> 99：1 dr以及高达98％的ee）。
• Synthesis of tetrahydrothiopyrano[2,3-<i>b</i>]indoles <i>via</i> [3+3] annulation of nitroallylic acetates with indoline-2-thiones
  作者：Pallabita Basu、Chiranjit Hazra、Thekke V. Baiju、Irishi N. N. Namboothiri

  DOI：10.1039/c9nj04754a

  日期：——

  and stereoselective synthesis of thiopyran annulated indoles. It involves a base mediated cascade [3+3] annulation of indoline-2-thiones and nitroallylic acetates. The tetrahydrothiopyranoindoles which were formed in good yields and in a short reaction time could be easily transformed to triazole derivatives by taking advantage of the nitro group present in the skeleton.

  已开发出一种有效的一锅法，用于区域和立体选择性合成噻吩并环的吲哚。它涉及吲哚啉-2-硫酮和硝基烯丙基乙酸盐的碱介导的级联[3 + 3]环化。利用骨架中存在的硝基，可以以高收率和短反应时间形成的四氢噻喃并吲哚易于转化为三唑衍生物。
• Chiral squaramide-catalyzed asymmetric synthesis of pyranones and pyranonaphthoquinones via cascade reactions of 1,3-dicarbonyls with Morita–Baylis–Hillman acetates of nitroalkenes
  作者：Divya K. Nair、Rubem F. S. Menna-Barreto、Eufrânio N. da Silva Júnior、Shaikh M. Mobin、Irishi N. N. Namboothiri

  DOI：10.1039/c4cc02279c

  日期：——

  Cascade reactions of 1,3-dicarbonyls with Morita-Baylis-Hillman acetates of nitroalkenes using a quinine derived chiral squaramide organocatalyst led to the formation of pyranones and pyranonaphthoquinones in good to excellent yields and high diastereo- and enantioselectivities. Representative examples of the reaction scale-up with a much lower catalyst loading without an appreciable loss of selectivities

  使用奎宁衍生的手性方酰胺有机催化剂，使1,3-二羰基化合物与硝基烯烃的森田-贝利斯-希尔曼乙酸酯级联反应，可形成吡喃酮和吡喃并萘醌，并具有良好的产率，高的非对映选择性和对映选择性。在此还报道了具有低得多的催化剂载量而没有明显的选择性损失和产物的合成转化的反应放大的代表性实例。由于结构与生物活性的α-拉帕酮有关，因此首次针对本文所述的化合物针对恰加斯氏病的病原体克氏锥虫的感染性血流形式进行了评估。
• Base and catalyst-free synthesis of nitrobenzodiazepines via a cascade N-nitroallylation-intramolecular aza-Michael addition involving o-phenylenediamines and nitroallylic acetates
  作者：Divya K. Nair、Sudheesh T. Sivanandan、Pravin Kendrekar、Irishi N.N. Namboothiri

  DOI：10.1016/j.tet.2019.130761

  日期：2019.12