(E)-β-(3,5-dimethoxyphenyl)-vinyl iodide | 956499-10-8

• 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)-β-(3,5-dimethoxyphenyl)-vinyl iodide
• 英文别名: 1-[(E)-2-iodoethenyl]-3,5-dimethoxybenzene
• CAS: 956499-10-8
• 化学式: C₁₀H₁₁IO₂
• 分子量: 290.101
• InChiKey: QDCWASGULWEGGQ-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-β-(3,5-dimethoxyphenyl)-vinyl iodide 、 4-甲氧基苯酚 在 N-甲基吗啉 、 caesium carbonate 、 copper(l) chloride 作用下， 以 甲苯 为溶剂， 以62%的产率得到1,3-dimethoxy-5-[(E)-2-(4-methoxyphenoxy)ethenyl]benzene
  参考文献：
  名称：

  New classes of Gram-positive selective antibacterials: Inhibitors of MRSA and surrogates of the causative agents of anthrax and tuberculosis

  摘要：

  An antimicrobial phenolic stilbene, (E)-3-hydroxy-5-methoxystilbene, 1 was recently isolated from the leaves of Comptonia peregrina (L.) Coulter and shown to possess inhibitory activity against several Gram-positive bacteria, including isolates of methicillin-resistant Staphylococcus aureus (MRSA), Mycobacterium bovis BCG, and avirulent Bacillus anthracis (Sterne strain), among others. These results prompted the design and synthesis of two new classes of compounds, phenoxystyrenes and phenothiostyrenes, as analogs of the natural antimicrobial stilbene. These and additional stilbenoid analogs were synthesized using new, efficient, copper-mediated coupling strategies. Minimum inhibitory concentration (MIC) antimicrobial assays were performed on all compounds prepared. These preliminary structure-activity relationship studies indicated that both new classes of synthetic analogs, as well as the stilbenes, show promising activity against Gram-positive bacteria when at least one phenolic moiety is present, but not when absent. The potencies of the phenolic phenoxystyrenes and phenothiostyrenes were found to be comparable to those of the phenolic stilbenes tested. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.085
• 作为产物：
  描述：

  碘仿 、 3,5-二甲氧基苯甲醛 在 chromium dichloride 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到(E)-β-(3,5-dimethoxyphenyl)-vinyl iodide
  参考文献：
  名称：

  一种高效多功能配体在铜催化乙烯基卤化物与 N-杂环和酚的交叉偶联反应中的首次应用

  摘要：

  2-Pyridin-2-yl-1H-benzoimidazole L3 是一种新型、高效、多功能的双齿 N 供体配体，适用于铜催化形成乙烯基 CN 和 CO 键。这种廉价且易于制备的配体促进了铜催化的烯基溴化物和碘化物与N-杂环和酚的交叉偶联反应，以良好至极好的收率提供所需的交叉偶联产物，并完全保留立体化学。这种方法特别值得注意，因为它的效率，即温和的反应条件、低催化剂负载、简单、多功能和优异的官能团耐受性。

  DOI：

  10.1021/ol9026446

文献信息

• Stereospecific Iron-Catalyzed Carbon (sp²)–Carbon (sp²) Cross-Coupling of Aryllithium with Vinyl Halides
  作者：Peng Chen、Zhi-Yong Wang、Xiao-Shui Peng、Henry N.C. Wong

  DOI：10.1021/acs.orglett.1c01318

  日期：2021.6.4

  We present herein an efficient synthetic protocol involving iron-catalyzed cross-coupling of organolithium compounds with vinyl halides as key coupling partners. More than 30 examples were obtained with moderate to good yields and high stereoselectivities. The practicality of this method is evidenced by a gram-scale synthesis. In addition, a preliminary mechanistic investigation was also performed

  我们在此提出了一种有效的合成方案，涉及有机锂化合物与乙烯基卤化物作为关键偶联伙伴的铁催化交叉偶联。获得了 30 多个具有中等至良好产率和高立体选择性的实例。克级合成证明了该方法的实用性。此外，还进行了初步的机械调查。
• Palladium-Catalyzed Fluorosulfonylvinylation of Organic Iodides
  作者：Gao-Feng Zha、Qinheng Zheng、Jing Leng、Peng Wu、Hua-Li Qin、K. Barry Sharpless

  DOI：10.1002/anie.201701162

  日期：2017.4.18

  A palladium‐catalyzed fluorosulfonylvinylation reaction of organic iodides is described. Catalytic Pd(OAc)2 with a stoichiometric amount of silver(I) trifluoroacetate enables the coupling process between either an (hetero)aryl or alkenyl iodide with ethenesulfonyl fluoride (ESF). The method is demonstrated in the successful syntheses of eighty‐eight otherwise difficult to access compounds, in up to

  描述了钯催化的有机碘的氟磺酰基乙烯基化反应。具有化学计量的三氟乙酸银（I）的催化Pd（OAc）2使（杂）芳基或烯基碘化物与乙磺酰氟（ESF）之间的偶联过程成为可能。该方法已成功合成了88种原本难以接近的化合物，收率高达99％，其中包括前所未有的2-杂芳基磺酰氟和1,3-二烯基磺酰氟。
• ANTI-INFECTIVE AGENTS AND METHODS OF USE
  申请人：Monte Aaron

  公开号：US20070292545A1

  公开（公告）日：2007-12-20

  The present invention provides compounds and methods of using of the compounds as anti-infective agents. In a preferred embodiment, the present invention provides wherein R 1 is not H when R 2 is H and R 2 is not H when R 1 is H, further wherein R 1 is CH (2n+1) O, wherein n is 1-10; wherein R 2 is OH or CH (2n+1) O, wherein n is 1-10; and wherein A, B and R 1 , R 2 , R 5 , R 6 , and R 7 are independently selected from a group consisting of H, alkyl and aryl groups and R 11 is an alkyl or an aryl group

  本发明提供化合物及其使用方法作为抗感染剂。在一种优选实施例中，本发明提供其中R1不是H时，R2是H，且R2不是H时，R1是H，进一步地，其中R1是CH（2n+1）O，其中n为1-10；其中R2是OH或CH（2n+1）O，其中n为1-10；以及其中A、B和R1、R2、R5、R6和R7分别独立地选自H、烷基和芳基基团，而R11是烷基或芳基基团。
• Broad Spectrum Gram-Positive Antimicrobials and Anthelmintics with Efficacy Against Drug-Resistant Strains and Mycobacterium Species
  申请人：Monte Aaron P.

  公开号：US20110092578A1

  公开（公告）日：2011-04-21

  The present invention provides compounds and methods of using of the compounds as anti-infective and anthelminitc agents. In a preferred embodiment, the present invention provides the following compound of Formula III: wherein: R 1 is not H when R 2 is H and R 2 is not H when R 1 is H, further wherein R 1 is OH or CH (2n+1) O, wherein n is 1-10; R 2 is OH or CH (2n+1) O, where n is 1-10; W is alkyl, phenyl, halophenyl, pyridyl, piperidyl, or a substituted or unsubstituted aryl group, including unsubstituted and substituted aromatic heterocycles; and L is an optional linker or linking group selected from O, S, NH, CF 2 , or CH 2 , and x=0 or 1, i.e., if x=0, no linking group is present.

  本发明提供了化合物及其使用方法，作为抗感染和驱虫剂。在一种优选实施例中，本发明提供以下III式化合物：其中：当R2为H时，R1不是H，当R1为H时，R2不是H，进一步地，其中R1为OH或CH（2n+1）O，其中n为1-10；R2为OH或CH（2n+1）O，其中n为1-10；W为烷基、苯基、卤代苯基、吡啶基、哌啶基或取代或未取代的芳基基团，包括未取代和取代的芳香杂环；L是可选的连接或连接基，选择自O、S、NH、CF2或CH2，x=0或1，即如果x=0，则不存在连接基。
• US8530512B2
  申请人：——

  公开号：US8530512B2

  公开（公告）日：2013-09-10