1-(2-nitroethenyl)-3,5-bis(trifluoromethyl)benzene | 253122-83-7

• 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: 1-(2-nitroethenyl)-3,5-bis(trifluoromethyl)benzene
• CAS: 253122-83-7
• 化学式: C₁₀H₅F₆NO₂
• 分子量: 285.146
• InChiKey: YWHRYXZJZWKPRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(2-nitroethenyl)-3,5-bis(trifluoromethyl)benzene 在 sodium tetrahydroborate 、 silica gel 作用下， 以 氯仿 、 异丙醇 为溶剂， 反应 2.0h， 以96%的产率得到1-(2-nitroethyl)-3,5-bis(trifluoromethyl)benzene
  参考文献：
  名称：

  Design, Synthesis, and Efficacy Testing of Nitroethylene- and 7-Nitrobenzoxadiazol-Based Flavodoxin Inhibitors against Helicobacter pylori Drug-Resistant Clinical Strains and in Helicobacter pylori-Infected Mice

  摘要：

  Helicobacter pylori (Hp) infection is the main cause of peptic ulcer and gastric cancer. Hp eradication rates have fallen due to increasing bacterial resistance to currently used broad-spectrum antimicrobials. We have designed, synthesized, and tested redox variants of nitroethylene- and 7-nitrobenzoxadiazole-based inhibitors of the essential Hp protein flavodoxin. Derivatives of the 7-nitrobenzoxadiazole lead, carrying reduced forms of the nitro group and/or oxidized forms of a sulfur atom, display high therapeutic indexes against several reference Hp strains. These inhibitors are effective against metronidazole-, clarithromycin-, and rifampicin-resistant Hp clinical isolates. Their toxicity for mice after oral administration is low, and, when administered individually at single daily doses for 8 days in a mice model of Hp infection, they decrease significantly Hp gastric colonization rates and are able to eradicate the infection in up to 60% of the mice. These flavodoxin inhibitors constitute a novel family of Hp-specific antimicrobials that may help fight the constant increase of Hp antimicrobial-resistant strains.

  DOI：

  10.1021/acs.jmedchem.9b00355
• 作为产物：
  描述：

  硝基甲烷 、 3,5-双(三氟甲基)苄胺 在 4-(4-fluorophenyl)naphthalene-1,2-dione 、 氧气 作用下， 反应 12.0h， 以30%的产率得到1-(2-nitroethenyl)-3,5-bis(trifluoromethyl)benzene
  参考文献：
  名称：

  邻萘醌催化剂的基质混杂性：脱氧性交叉偶联和N-亚硝化的催化好氧胺氧化方案。

  摘要：

  基于邻萘醌的有机催化剂已被鉴定为通用的好氧氧化催化剂。伯胺很容易通过脱氨途径与伯硝基烷烃交联，从而以良好或优异的收率得到硝基烯烃衍生物。仲胺和叔胺对邻萘醌催化剂是惰性的。然而，仲硝基烷烃很容易通过邻萘醌催化剂转化为相应的亚硝酸盐类，后者将胺原位氧化为相应的N。-亚硝基化合物。在不以化学计量的量使用刺激性氧化剂的情况下，本催化好氧氧化方案利用底物的混杂特性在温和的反应条件下提供了容易的胺氧化产物的通道。

  DOI：

  10.1021/acscatal.9b03442

文献信息

• Synthesis of Chiral Cyclic Nitrones by Asymmetric Addition of β-Ketosulfones to Nitroalkenes followed by Reductive Cyclization
  作者：Olga García Mancheño、Pia Tangen、Renate Rohlmann、Roland Fröhlich、José Alemán

  DOI：10.1002/chem.201001914

  日期：2011.1.17

  transformed into chiral nitrones by reduction of the nitro group and in situ cyclization (up to 99:1 e.r. and >98:2 d.r.). Moreover, the utility of this method has additionally been demonstrated by the further transformation to functionalized N‐hydroxypyrrolidines that possess a quaternary center by addition of trimethylsilyl cyanide (TMSCN) to the CN bond of the cyclic nitrones in the presence of a

  介绍了硫脲金鸡纳生物碱催化的β-酮砜第一次有机催化加成至硝基烯烃。通过还原硝基和原位环化（高达99：1 er和> 98：2 dr），将容易获得的加成产物选择性转化为手性硝酮。此外，通过在路易斯酸存在下将三甲基甲硅烷基氰化物（TMSCN）加到环状硝酮的CN键上，进一步转化为具有季中心的官能化N-羟基吡咯烷，进一步证明了该方法的实用性。。
• Direct Synthesis of N-Unsubstituted 4-Aryl-1,2,3-triazoles Mediated by Amberlyst-15
  作者：Zu-Li Wang、Hui Zhang、Dao-Qing Dong

  DOI：10.1055/s-0035-1560488

  日期：——

  A highly efficient and effective method for the synthesis of N-unsubstituted 4-aryl-1,2,3-triazoles promoted by Amberlyst-15 is described. The promoter can be recycled and reused up to eight times without any reduction in its catalytic activity.
• Substrate Promiscuity of <i>ortho</i>-Naphthoquinone Catalyst: Catalytic Aerobic Amine Oxidation Protocols to Deaminative Cross-Coupling and <i>N</i>-Nitrosation
  作者：Tengda Si、Hun Young Kim、Kyungsoo Oh

  DOI：10.1021/acscatal.9b03442

  日期：2019.10.4

  been identified as versatile aerobic oxidation catalysts. Primary amines were readily cross-coupled with primary nitroalkanes via deaminative pathway to give nitroalkene derivatives in good to excellent yields. Secondary and tertiary amines were inert to ortho-naphthoquinone catalysts; however, secondary nitroalkanes were readily converted by ortho-naphthoquinone catalysts to the corresponding nitrite

  基于邻萘醌的有机催化剂已被鉴定为通用的好氧氧化催化剂。伯胺很容易通过脱氨途径与伯硝基烷烃交联，从而以良好或优异的收率得到硝基烯烃衍生物。仲胺和叔胺对邻萘醌催化剂是惰性的。然而，仲硝基烷烃很容易通过邻萘醌催化剂转化为相应的亚硝酸盐类，后者将胺原位氧化为相应的N。-亚硝基化合物。在不以化学计量的量使用刺激性氧化剂的情况下，本催化好氧氧化方案利用底物的混杂特性在温和的反应条件下提供了容易的胺氧化产物的通道。
• Design, Synthesis, and Efficacy Testing of Nitroethylene- and 7-Nitrobenzoxadiazol-Based Flavodoxin Inhibitors against <i>Helicobacter pylori</i> Drug-Resistant Clinical Strains and in <i>Helicobacter pylori</i>-Infected Mice
  作者：Sandra Salillas、Miriam Alías、Valérie Michel、Alejandro Mahía、Ainhoa Lucía、Liliana Rodrigues、Jessica Bueno、Juan José Galano-Frutos、Hilde De Reuse、Adrián Velázquez-Campoy、José Alberto Carrodeguas、Carlos Sostres、Javier Castillo、José Antonio Aínsa、María Dolores Díaz-de-Villegas、Ángel Lanas、Eliette Touati、Javier Sancho

  DOI：10.1021/acs.jmedchem.9b00355

  日期：2019.7.11

  Helicobacter pylori (Hp) infection is the main cause of peptic ulcer and gastric cancer. Hp eradication rates have fallen due to increasing bacterial resistance to currently used broad-spectrum antimicrobials. We have designed, synthesized, and tested redox variants of nitroethylene- and 7-nitrobenzoxadiazole-based inhibitors of the essential Hp protein flavodoxin. Derivatives of the 7-nitrobenzoxadiazole lead, carrying reduced forms of the nitro group and/or oxidized forms of a sulfur atom, display high therapeutic indexes against several reference Hp strains. These inhibitors are effective against metronidazole-, clarithromycin-, and rifampicin-resistant Hp clinical isolates. Their toxicity for mice after oral administration is low, and, when administered individually at single daily doses for 8 days in a mice model of Hp infection, they decrease significantly Hp gastric colonization rates and are able to eradicate the infection in up to 60% of the mice. These flavodoxin inhibitors constitute a novel family of Hp-specific antimicrobials that may help fight the constant increase of Hp antimicrobial-resistant strains.