2-chlorocyclohept-1-enecarbonitrile | 1254119-61-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 2-chlorocyclohept-1-enecarbonitrile
• 英文别名: 2-chlorocyclohept-1-ene-1-carbonitrile；2-chlorocycloheptene-1-carbonitrile
• CAS: 1254119-61-3
• 化学式: C₈H₁₀ClN
• 分子量: 155.627
• InChiKey: YBKMBXGFGWMBHN-UHFFFAOYSA-N

物化性质

• 沸点：
  247.6±39.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-chlorocyclohept-1-enecarbonitrile 在 15-冠醚-5 、 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 40.25h， 生成 2-Oxo-1-prop-2-enylcycloheptane-1-carbonitrile
  参考文献：
  名称：

  环腈中四元中心的对映选择性安装

  摘要：

  通过将醇盐与氯烯腈共轭加成，然后进行克莱森重排，四元中心快速且选择性地安装在一系列七元和桥连环状氧腈中。使用这种策略，仲烯丙醇中甲醇的立体信息被转移到新生成的季中心。实验上，该序列在一次合成操作中以良好的收率和高选择性快速得到烷基氰基环庚酮和双环烷酮甲腈。

  DOI：

  10.1002/ejoc.201500895
• 作为产物：
  描述：

  2-羰基-环庚烷甲腈 在 四氯化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以76%的产率得到2-chlorocyclohept-1-enecarbonitrile
  参考文献：
  名称：

  环状季腈的对映选择性合成

  摘要：

  五元，六元和七元的2-氯烯烃腈与手性醇通过克莱森重排的结合立体选择性地生成季腈。该策略基于新的共轭加成-将烯丙基醇盐消除到2-氯环烯腈中，得到取代的2-烷氧基烯腈。随后的热解反应会掩盖环状氧腈，同时选择性地形成对映体比率通常大于9：1的新季铵中心。整体烷基化策略解决了对映选择性地生成受阻的四级中心同时安装酮，腈和烯烃官能团的挑战。

  DOI：

  10.1021/jo1011202

文献信息

• From cycloheptathiophene-3-carboxamide to oxazinone-based derivatives as allosteric HIV-1 ribonuclease H inhibitors
  作者：Serena Massari、Angela Corona、Simona Distinto、Jenny Desantis、Alessia Caredda、Stefano Sabatini、Giuseppe Manfroni、Tommaso Felicetti、Violetta Cecchetti、Christophe Pannecouque、Elias Maccioni、Enzo Tramontano、Oriana Tabarrini

  DOI：10.1080/14756366.2018.1523901

  日期：2019.1.1

  Abstract The paper focussed on a step-by-step structural modification of a cycloheptathiophene-3-carboxamide derivative recently identified by us as reverse transcriptase (RT)-associated ribonuclease H (RNase H) inhibitor. In particular, its conversion to a 2-aryl-cycloheptathienoozaxinone derivative and the successive thorough exploration of both 2-aromatic and cycloheptathieno moieties led to identify

  抽象的 本文重点研究了最近被我们鉴定为逆转录酶（RT）相关的核糖核酸酶H（RNase H）抑制剂的环庚噻吩-3-甲酰胺衍生物的逐步结构修饰。特别地，其向2-芳基-环庚硫基杂氮杂酮衍生物的转化以及对2-芳族和环庚二硫基部分的连续深入探索导致将基于恶嗪酮的化合物鉴定为新的抗RNA酶H化学型。支架C-2位置上邻苯二酚部分的出现对于实现有效的抗RNA酶H活性至关重要，该活性还包括三环衍生物的抗RNA依赖性DNA聚合酶（RDDP）活性。苯并噻吩并恶嗪酮衍生物22产生的最强双重抑制剂表现出IC 50相对于RNase H和RDDP功能的s分别为0.53和2.90μM。诱变和对接研究表明，化合物22结合了RT中的两个变构口袋，一个位于RNase H活性位点和引物结合区之间，另一个位于DNA聚合酶催化中心附近。
• Synthesis and characterization of 1,2,4-triazolo[1,5-a]pyrimidine-2-carboxamide-based compounds targeting the PA-PB1 interface of influenza A virus polymerase
  作者：Serena Massari、Chiara Bertagnin、Maria Chiara Pismataro、Anna Donnadio、Giulio Nannetti、Tommaso Felicetti、Stefano Di Bona、Maria Giulia Nizi、Leonardo Tensi、Giuseppe Manfroni、Maria Isabel Loza、Stefano Sabatini、Violetta Cecchetti、Jose Brea、Laura Goracci、Arianna Loregian、Oriana Tabarrini

  DOI：10.1016/j.ejmech.2020.112944

  日期：2021.1

  Influenza viruses (Flu) are responsible for seasonal epidemics causing high rates of morbidity, which can dramatically increase during severe pandemic outbreaks. Antiviral drugs are an indispensable weapon to treat infected people and reduce the impact on human health, nevertheless anti-Flu armamentarium still remains inadequate. In search for new anti-Flu drugs, our group has focused on viral RNA-dependent RNA polymerase (RdRP) developing disruptors of PA-PB1 subunits interface with the best compounds characterized by cycloheptathiophene-3-carboxamide and 1,2,4-triazolo[1,5-a]pyrimidine-2-carboxamide scaffolds. By merging these moieties, two very interesting hybrid compounds were recently identified, starting from which, in this paper, a series of analogues were designed and synthesized. In particular, a thorough exploration of the cycloheptathiophene-3-carboxamide moiety led to acquire important SAR insight and identify new active compounds showing both the ability to inhibit PA-PB1 interaction and viral replication in the micromolar range and at non-toxic concentrations. For few compounds, the ability to efficiently inhibit PA-PB1 subunits interaction did not translate into anti-Flu activity. Chemical/physical properties were investigated for a couple of compounds suggesting that the low solubility of compound 14, due to a strong crystal lattice, may have impaired its antiviral activity. Finally, computational studies performed on compound 23, in which the phenyl ring suitably replaced the cycloheptathiophene, suggested that, in addition to hydrophobic interactions, H-bonds enhanced its binding within the PAC cavity.
• Enantioselective Synthesis of Cyclic, Quaternary Oxonitriles
  作者：Yakup Güneş、M. Fatih Polat、Ertan Sahin、Fraser F. Fleming、Ramazan Altundas

  DOI：10.1021/jo1011202

  日期：2010.11.5

  Quaternary oxonitriles are stereoselectively generated from the union of five-, six-, and seven-membered 2-chloroalkenecarbonitriles with chiral alcohols via a Claisen rearrangement. The strategy rests on a new conjugate addition−elimination of allylic alkoxides to 2-chlorocycloalkenecarbonitriles to afford substituted 2-alkoxyalkenenitriles. Subsequent thermolysis unmasks a cyclic oxonitrile while

  五元，六元和七元的2-氯烯烃腈与手性醇通过克莱森重排的结合立体选择性地生成季腈。该策略基于新的共轭加成-将烯丙基醇盐消除到2-氯环烯腈中，得到取代的2-烷氧基烯腈。随后的热解反应会掩盖环状氧腈，同时选择性地形成对映体比率通常大于9：1的新季铵中心。整体烷基化策略解决了对映选择性地生成受阻的四级中心同时安装酮，腈和烯烃官能团的挑战。
• Enantioselective Installation of Quaternary Centers in Cyclic Oxonitriles
  作者：Yakup Gunes、Nejat Arcelik、Ertan Sahin、Fraser F. Fleming、Ramazan Altundas

  DOI：10.1002/ejoc.201500895

  日期：2015.10

  Quaternary centers are rapidly and selectively installed in a series of seven-membered and bridged cyclic oxonitriles through conjugate addition of an alkoxide to chloroalkenenitriles, followed by a Claisen rearrangement. Using this strategy, the stereogenic information of the carbinol in secondary allylic alcohols is transferred to the newly generated quaternary center. Experimentally, the sequence

  通过将醇盐与氯烯腈共轭加成，然后进行克莱森重排，四元中心快速且选择性地安装在一系列七元和桥连环状氧腈中。使用这种策略，仲烯丙醇中甲醇的立体信息被转移到新生成的季中心。实验上，该序列在一次合成操作中以良好的收率和高选择性快速得到烷基氰基环庚酮和双环烷酮甲腈。