(E)-4-cyanocinnamyl bromide | 99154-08-2

• 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: (E)-4-cyanocinnamyl bromide
• 英文别名: p-Cyancinnamylbromid；(E)-4-(3-Bromoprop-1-en-1-yl)benzonitrile；4-[(E)-3-bromoprop-1-enyl]benzonitrile
• CAS: 99154-08-2
• 化学式: C₁₀H₈BrN
• 分子量: 222.084
• InChiKey: CSDPTLGTZDYFHA-OWOJBTEDSA-N

物化性质

• 沸点：
  327.0±30.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  (E)-4-cyanocinnamyl bromide 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 (1R,4S,8S)-3-aza-8-(4-cyanophenyl)-4-isopropyl-3-(2,4,6-trimethylphenylsulfonyl)bicyclo[4.2.0]oct-5-ene
  参考文献：
  名称：

  双环[4.2.0] oct-5-ene衍生物通过丙二烯的热分子内[2 + 2]环加成反应形成的高区域选择性和立体选择性

  摘要：

  描述了具有额外多重键的丙二烯的热[2 + 2]环加成。通过在适当的溶剂（例如二恶烷或DMF）中简单地加热具有三原子系链的烯丙基或烯丙基，烯丙基部分的远端双键区域选择性地参与环加成反应，形成双环[4.2.0] oct-5-ene衍生物产量高到极好。在丙二烯的所有反应中，烯烃的几何结构已完全转移至环加合物。虽然末端异戊烯的反应提供了作为单一异构体的双环环丁烷衍生物，但是一些具有轴向手性的内部异丁烯的环加成产生了环加合物的非对映异构体混合物。这些结果与通过具有共平面的烯丙基的双自由基中间体的逐步机理很好地一致。

  DOI：

  10.1021/jo0700528
• 作为产物：
  描述：

  p-cyanocinnamaldehyde 在 sodium tetrahydroborate 、 氢溴酸 作用下， 生成 (E)-4-cyanocinnamyl bromide
  参考文献：
  名称：

  Zahl,G. et al., Justus Liebigs Annalen der Chemie, 1975, p. 1733 - 1743

  摘要：

  DOI：

文献信息

• Allylic and Allenic Halide Synthesis via NbCl₅- and NbBr₅-Mediated Alkoxide Rearrangements
  作者：P. C. Ravikumar、Lihua Yao、Fraser F. Fleming

  DOI：10.1021/jo901287f

  日期：2009.10.2

  Addition of NbCl5 or NbBr5 to a series of magnesium, lithium, or potassium allylic or propargylic alkoxides directly provides allylic or allenic halides. Halogenation formally occurs through a metalla-halo-[3,3] rearrangement, although concerted, ionic, and direct displacement mechanisms appear to operate competitively. Transposition of the olefin is equally effective for allylic alkoxides prepared

  将NbCl 5或 NbBr 5 添加到一系列镁、锂或钾的烯丙基或炔丙基醇盐中直接提供烯丙基或烯丙基卤化物。卤化通过金属-卤-[3,3] 重排正式发生，尽管协同、离子和直接置换机制似乎具有竞争性。烯烃的转位对于通过亲核加成、去质子化或还原制备的烯丙基醇盐同样有效。实验上，五卤化铌卤化反应迅速，萃取后可提供基本纯的 ( E )-烯丙基或烯丙基卤化物，适用于一系列脂肪族和芳香族醇、醛和酮。
• Palladium-Catalyzed Reductive Aminocarbonylation of <i>o</i>-Iodophenol-Derived Allyl Ethers with <i>o</i>-Nitrobenzaldehydes to 3-Alkenylquinolin-2(1<i>H</i>)-ones
  作者：Jian-Li Liu、Wei Wang、Xinxin Qi、Xiao-Feng Wu

  DOI：10.1021/acs.orglett.2c00648

  日期：2022.3.25

  An attractive palladium-catalyzed reductive aminocarbonylation reaction of allylic ethers has been explored for the synthesis of 3-alkenylquinolin-2(1H)-one derivatives. With Mo(CO)6 as both CO surrogate and reductant, a variety of 3-alkenylquinolin-2(1H)-ones were obtained in good to excellent yields from o-iodophenol-derived allyl ethers with o-nitrobenzaldehydes as the nitrogen sources. This reaction

  已经探索了一种有吸引力的钯催化的烯丙基醚的还原氨基羰基化反应，用于合成 3-alkenylquinolin-2(1 H )-one 衍生物。以Mo(CO) 6作为CO 替代物和还原剂，以邻硝基苯甲醛为氮源，由邻碘苯酚衍生的烯丙基醚以良好至优异的收率获得了多种3-alkenylquinolin-2(1 H )-one . 该反应通过级联途径进行，不依赖于以前的烯丙基羰基化反应所需的高压 CO 气体。该策略为构建 3-alkenylquinolin-2(1 H )-ones 提供了新途径。
• Organic compounds and their pharmaceutical use
  申请人：Lilly Industries Limited

  公开号：EP0146333A1

  公开（公告）日：1985-06-26

  @ There is described compounds of the formula in which R1 is hydrogen or C1-6alkyl, R2 is hydrogen, C1-6 alkyl or C3-6 alkenyl, and X is -CH = CH- or -(CH2)n- where n is 1 to 3, and Y is -CN or and salts thereof. The compounds in which Y is tetrazolyl possess pharmaceutical activity.

  @ 描述了式中的化合物 其中 R1 是氢或 C1-6 烷基，R2 是氢、C1-6 烷基或 C3-6 烯基，X 是-CH = CH- 或-(CH2)n-，其中 n 是 1 至 3，Y 是-CN 或 及其盐类。Y 为四唑基的化合物具有药物活性。
• Novel Inhibitors of Staphyloxanthin Virulence Factor in Comparison with Linezolid and Vancomycin versus Methicillin-Resistant, Linezolid-Resistant, and Vancomycin-Intermediate <i>Staphylococcus aureus</i> Infections in Vivo
  作者：Shuaishuai Ni、Hanwen Wei、Baoli Li、Feifei Chen、Yifu Liu、Wenhua Chen、Yixiang Xu、Xiaoxia Qiu、Xiaokang Li、Yanli Lu、Wenwen Liu、Linhao Hu、Dazheng Lin、Manjiong Wang、Xinyu Zheng、Fei Mao、Jin Zhu、Lefu Lan、Jian Li

  DOI：10.1021/acs.jmedchem.7b00949

  日期：2017.10.12

  Our previous work (Wang et al. J. Med. Chem. 2016, 59, 4831-4848) revealed that effective benzocycloalkane-derived staphyloxanthin inhibitors against methicillin-resistant Staphylococcus aureus (S. aureus) infections were accompanied by poor water solubility and high hERG inhibition and dosages (preadministration). In this study, 92 chroman and coumaran derivatives as novel inhibitors have been addressed for overcoming deficiencies above. Derivatives 69 and 105 displayed excellent pigment inhibitory activities and low hERG inhibition, along with improvement of solubility by salt type selection. The broad and significantly potent antibacterial spectra of 69 and 105 were displayed first with normal administration in the livers and hearts in mice against pigmented S. aureus Newman, Mu50 (vancomycin-intermediate S. aureus), and NRS271 (linezolid-resistant S. aureus), compared with linezolid and vancomycin. In summary, both 69 and 105 have the potential to be developed as good antibacterial candidates targeting virulence factors.
• Novel Staphyloxanthin Inhibitors with Improved Potency against Multidrug Resistant <i>Staphylococcus aureus</i>
  作者：Shuaishuai Ni、Baoli Li、Feifei Chen、Hanwen Wei、Fei Mao、Yifu Liu、Yixiang Xu、Xiaoxi Qiu、Xiaokang Li、Wenwen Liu、Linghao Hu、Dazheng Ling、Manjiong Wang、Xinyu Zheng、Jin Zhu、Lefu Lan、Jian Li

  DOI：10.1021/acsmedchemlett.7b00501

  日期：2018.3.8

  Diapophytoene desaturase (CrtN) is a potential novel target for intervening in the biosynthesis of the virulence factor staphyloxanthin. In this study, 38 1,4-benzodioxan-derived CrtN inhibitors were designed and synthesized to overwhelm the defects of leading compound 4a. Derivative 47 displayed superior pigment inhibitory activity, better hERG inhibitory properties and water solubility, and significantly sensitized MRSA strains to immune clearance in vitro. Notably, 47 displayed excellent efficacy against pigmented S. aureus Newman, Mu50 (vancomycin-intermediate MRSA, VISA), and NRS271 (linezolid-resistant MRSA, LRSA) comparable to that of linezolid and vancomycin in vivo.