3,3'-dimethoxystilbene | 6325-63-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 3,3'-dimethoxystilbene
• 英文别名: 3,3'-Dimethoxy-stilben；3,3'-Dimethoxy-stilbene；1-methoxy-3-[2-(3-methoxyphenyl)ethenyl]benzene
• CAS: 6325-63-9
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: ZBFPZUMLGZJSNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  3,3'-dimethoxystilbene 在 palladium on activated charcoal 、 三溴化硼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 3,3'-(ethane-1,2-diyl)diphenol
  参考文献：
  名称：

  A Bisphenolic Honokiol Analog Outcompetes Oral Antimicrobial Agent Cetylpyridinium Chloride via a Membrane-Associated Mechanism

  摘要：

  Targeting Streptococcus mutans is the primary focus in reducing dental caries, one of the most common maladies in the world. Previously, our groups discovered a potent bactericidal biaryl compound that was inspired by the natural product honokiol. Herein, a structure activity relationship (SAR) study to ascertain structural motifs key to inhibition is outlined. Furthermore, mechanism studies show that bacterial membrane disruption is central to the bacterial growth inhibition. During this process, it was discovered that analog C2 demonstrated a 4-fold better therapeutic index compared to the commercially available antimicrobial cetylpyridinium chloride (CPC) making it a viable alternative for oral care.

  DOI：

  10.1021/acsinfecdis.9b00190
• 作为产物：
  描述：

  3-methoxybenzaldehyde tosylhydrazone 在 硼酸三甲酯 、 lithium tert-butoxide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.0h， 以88%的产率得到3,3'-dimethoxystilbene
  参考文献：
  名称：

  Synthesis of stilbenes via homocoupling of aryl aldehyde tosylhydrazones

  摘要：

  Stilbenes are readily prepared in good yields via homocoupling of aryl aldehyde tosylhydrazones in the presence of lithium tert-butoxide and trimethyl borate under reflux in THF. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00859-0

文献信息

• B( <scp> C ₆ F ₅ </scp> ) <scp> ₃ ‐Catalyzed </scp> Hydroboration of Alkenes with <scp> <i>N</i> ‐Heterocyclic </scp> Carbene Boranes <i>via</i> B—H Bond Activation
  作者：Qiaotian Wang、Wei Meng、Xiangqing Feng、Haifeng Du

  DOI：10.1002/cjoc.202000489

  日期：2021.4

  Significantly, excellent regioselectivities were obtained in some cases. Mechanistic studies indicate that the B—H bond cleavage is likely involved in the rate‐determining step. In addition, an electrophilic addition of NHC‐borenium cation to alkenes and the subsequent formation of carbocation are also postulated. The current work provides a promising method for the activation of stable borane adducts

  在这项工作中，开发了一种新的活化N-杂环卡宾硼烷（NHC-硼烷）的方式，该方式是通过以沮丧的Lewis对方式通过路易斯酸B（C 6 F 5）3氢化物提取生成高反应性的两性离子物质。B（C 6 F 5）3的合适底物包括苯乙烯，β-甲基苯乙烯，苯乙烯和烷基烯烃等多种烯烃。催化硼氢化以高至高收率提供所需的产品。显着地，在某些情况下获得了优异的区域选择性。机理研究表明，在确定速率的步骤中可能涉及到B键的断裂。此外，还假定将NHC-硼阳离子亲电加成到烯烃中，并随后形成碳正离子。目前的工作为稳定硼烷加合物的活化提供了一种有前途的方法，这可能在将来引起一些有趣的转变。
• The effect of aryl substituents on arylcarbene reactivity
  作者：Hideo Tomioka、Kazuo Tabayashi、Yasuji Ozaki、Yasuji Izawa

  DOI：10.1016/s0040-4020(01)96384-7

  日期：1985.1

  and cyclohexane) and the relative rate of O—H insertion into methanol to stereospecific cyclopropanation of the olefin to C—H insertion into cyclohexane are calculated from the ratios of products and substrates. It is found (i) that the reactivities of the substrates decrease in the order of methanol, olefin and cyclohexane and (ii) that electron-donating substituents generally lead to reaction with

  取代的（p -MeO，p -Me，H，p -Cl，p -Br，m-Br，m-MeO，3,4-Cl 2，p -CO 2 Me，m-CN和p -CN）单苯基卡宾在底物的二元混合物（甲醇，顺式根据产物和底物的比例，计算出-4-甲基-2-戊烯和环己烷的OH插入到甲醇中烯烃的立体定向环丙烷化和OH插入到环己烷中的相对比率。发现（i）底物的反应性按甲醇，烯烃和环己烷的顺序降低，和（ii）供电子取代基通常导致与反应性较高的底物反应，而有利于与反应性较低的底物反应。在吸电子取代基的情况下。这些结果是通过取代基改变单线芳基卡宾的亲电性而不是单线态-三重态平衡的改变来解释的。
• Effect of base on alkyltriphenylphosphonium salts in polar aprotic solvents
  作者：Julius N Ngwendson、Cassandra M Schultze、Jordan W Bollinger、Anamitro Banerjee

  DOI：10.1139/v08-056

  日期：2008.7.1

  When arylmethyl phosphonium salts are treated with a base (e.g., t-BuOK or NaH) they homocouple to form symmetric 1,2-diarylethenes. In some cases, dilution and (or) use of excess base lead to very...

  当芳甲基鏻盐用碱（例如，t-BuOK 或 NaH）处理时，它们均偶合形成对称的 1,2-二芳基乙烯。在某些情况下，稀释和（或）使用过量的碱会导致非常……
• Assisted Tandem Catalytic Cross Metathesis–Oxidation: In One Flask from Styrenes to 1,2-Diketones and Further to Quinoxalines
  作者：Bernd Schmidt、Stefan Krehl、Sylvia Hauke

  DOI：10.1021/jo4005684

  日期：2013.6.7

  synthesized from styrenes by combining a cross metathesis and a Ru-catalyzed alkene oxidation to an assisted tandem catalytic sequence. The synthesis relies on the use of just one metathesis precatalyst, which was in situ converted to the oxidation catalyst by addition of an alkyl hydroperoxide as a chemical trigger and oxidant. The one-flask sequence can be extended beyond 1,2-diketones to quinoxalines, by

  通过结合交叉复分解和Ru催化的烯烃氧化至辅助串联催化序列，由苯乙烯合成1,2-二酮。合成依赖于仅使用一种易位预催化剂，该预催化剂通过加入烷基氢过氧化物作为化学触发剂和氧化剂而原位转化为氧化催化剂。通过氧化产物与邻苯二胺的缩合，一个烧瓶的序列可以扩展到1,2-二酮以外的喹喔啉。
• Substituent Effect Studies of Aryl-Assisted Solvolyses. I. The Acetolysis of 2,2-Bis(substituted phenyl)ethyl<i>p</i>-Toluenesulfonates
  作者：Mizue Fujio、Yasuyuki Maeda、Mutsuo Goto、Yoshihiro Saeki、Masaaki Mishima、Yuho Tsuno

  DOI：10.1246/bcsj.66.3015

  日期：1993.10

  The substituent effect on the acetolysis of 2,2-bis(substituted phenyl)ethyl p-toluenesulfonates at 90.10 °C can be described accurately in terms of the Yukawa–Tsuno (LArSR) relationship, giving a ρ value of −4.44 and an r value of 0.53. The substituent effect correlation of this system carrying two aryls is quite comparable to that of the 2-methyl-2-phenylpropyl system carrying a single aryl group, suggesting the close similarity in the structure of the transition states between the systems. The results can be reasonably accounted for on the basis of the accepted mechanism of this reaction, involving a rate-determining aryl-assisted transition state where only one aryl group of the two β-aryl groups participates.

  在90.10 °C下，2,2-双（取代苯基）乙基对甲苯磺酸酯的醇解反应中，取代基效应可以通过Yukawa–Tsuno（LArSR）关系进行准确描述，给出了ρ值为−4.44和r值为0.53。该系统中包含两个芳香基的取代基效应与包含单个芳香基的2-甲基-2-苯基丙基系统的相关性相当可比，这表明这两个系统的过渡态结构非常相似。根据这种反应的公认机制，结果可以合理地解释为涉及一个速率决定的芳基辅助过渡态，其中两个β-芳基中的仅一个芳基参与反应。