methyl 2-[(E)-2-(4-methylphenyl)ethenyl]benzoate

• 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: methyl 2-[(E)-2-(4-methylphenyl)ethenyl]benzoate
• 英文别名: (E)-methyl 2-(4-methylstyryl)benzoate；methyl (E)-2-(4-methylstyryl)benzoate；methyl 2-(4-methylstyryl)benzoate
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: FMJLCBZBMOONOS-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 2-[(E)-2-(4-methylphenyl)ethenyl]benzoate 在 5percent Pd/C 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、253.33 kPa 条件下， 反应 0.67h， 以74%的产率得到methyl 2-(4-methylphenethyl)benzoate
  参考文献：
  名称：

  4-Aminoquinolines:  Novel Nociceptin Antagonists with Analgesic Activity

  摘要：

  Small-molecule nociceptin antagonists were synthesized to examine their therapeutic potential. After a 4-aminoquinoline derivative was found to bind with the human ORL1 receptor, a series of 4-aminoquinolines and related compounds were synthesized and their binding was evaluated. Elucidation of structure-activity relationships eventually led to the optimum compounds. One of the se compounds, N-(4-amino-2-methylquinolin-6-yl) -2-(4-ethylphenoxymethyl)benzamide hydrochloride (11) not only antagonized nociceptin-induced allodynia in mice but also showed analgesic effect in a hot plate test using mice and in a formalin test using rats. Its analgesic effect was not antagonized by the opioid antagonist naloxone. These results indicate that this nociceptin antagonist has the potential to become a novel type of analgesic that differs from mu -opioid agonists.

  DOI：

  10.1021/jm0002073
• 作为产物：
  描述：

  4-methylcinnamic acid 、 2-碘苯甲酸甲酯 在 silver carbonate 、 palladium dichloride 、 2-(二环己基膦基)联苯 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 12.0h， 以60%的产率得到methyl 2-[(E)-2-(4-methylphenyl)ethenyl]benzoate
  参考文献：
  名称：

  肉桂酸与芳基碘化物的钯催化脱羧交叉偶联†

  摘要：

  高效脱羧交联反应 肉桂酸 与芳基碘化物的组合催化 氯化钯描述了在Ag 2 CO 3作为添加剂存在下的CyJohnPhos和CyJohnPhos 。所需的碳-碳键的形成以良好的官能团耐受性有效地进行。

  DOI：

  10.1039/b821870f

文献信息

• Diselenide- and Disulfide-Mediated Synthesis of Isocoumarins
  作者：Sohail A. Shahzad、Claire Venin、Thomas Wirth

  DOI：10.1002/ejoc.201000308

  日期：——

  Cyclizations of stilbenecarboxylic acids to the corresponding isocoumarin derivatives using diselenide or disulfide reagents have been developed. By employing bis(triflouroacetoxy)iodobenzene as oxidant for the 6-endo-trig cyclizations a variety of dihydroisocoumarins have been prepared in good yields. This method is capable of forming isocoumarins and dihydroisocoumarin derivatives by a cyclization–elimination

  已经开发出使用二硒化物或二硫化物试剂将芪甲酸环化为相应的异香豆素衍生物。通过使用双（三氟乙酰氧基）碘苯作为 6-endo-trig 环化的氧化剂，已经以良好的收率制备了多种二氢异香豆素。该方法能够通过环化-消除路线形成异香豆素和二氢异香豆素衍生物。
• An Easy-to-Machine Electrochemical Flow Microreactor: Efficient Synthesis of Isoindolinone and Flow Functionalization
  作者：Ana A. Folgueiras-Amador、Kai Philipps、Sébastien Guilbaud、Jarno Poelakker、Thomas Wirth

  DOI：10.1002/anie.201709717

  日期：2017.11.27

  Very little supporting electrolyte or none at all is needed in flow electrochemistry. Recycling and waste problems are eliminated as cyclization products are obtained in a fast and clean process.

  流动电化学中需要很少的辅助电解质或根本不需要。由于在快速，清洁的过程中获得了环化产品，因此消除了回收和废物问题。
• Selenium-Mediated Synthesis of Biaryls through Rearrangement
  作者：Sohail A. Shahzad、Clotilde Vivant、Thomas Wirth

  DOI：10.1021/ol100274e

  日期：2010.3.19

  A new cyclization of β-keto ester substituted stilbene derivatives using selenium electrophiles in the presence of Lewis acids is described. Substituted naphthols are obtained through cyclization and subsequent 1,2-rearrangement of aryl groups under very mild reaction conditions.

  描述了在路易斯酸存在下使用硒亲电试剂对β-酮酯取代的二苯乙烯衍生物进行的新环化。取代的萘酚是通过环化以及随后在非常温和的反应条件下对芳基进行1,2-重排而获得的。
• Metal‐ and Oxidant‐Free Electrosynthesis of Heterocycles from 1,2‐Diarylalkene Derivatives
  作者：Eunsoo Yu、Hyungguk Kim、Cheol‐Min Park

  DOI：10.1002/adsc.202200847

  日期：2022.12.8

  Synthesis of heterocycles from 1,2-diarylalkene derivatives through electrosynthesis under metal- and oxidant-free conditions has been discovered. Cathodic reduction of 2-alkenylbenzoic acid or anodic oxidation of 2-alkenylbenzamide, 2-alkenylphenol and 2-alkenylaniline leads to the formation of reactive radical intermediates which afford corresponding phthalide, isochroman-1-one, isoindolin-1-one

  已经发现在无金属和无氧化剂的条件下通过电合成从 1,2-二芳基烯烃衍生物合成杂环。2-烯基苯甲酸的阴极还原或 2-烯基苯甲酰胺、2-烯基苯酚和 2-烯基苯胺的阳极氧化导致反应性自由基中间体的形成，这些中间体提供相应的苯酞、异色满-1-酮、异吲哚啉-1-酮、苯并呋喃和吲哚以良好的官能团耐受性满足产量。有趣的是，在不同的反应溶剂中发现了不同的化学选择性。进行了几项机理研究，包括循环伏安法研究和控制实验，以阐明反应机理。
• 5-<i>exo</i>-Selective asymmetric bromolactonization of stilbenecarboxylic acids catalyzed by phenol-bearing chiral thiourea
  作者：Masayuki Sugano、Tsubasa Inokuma、Yousuke Yamaoka、Ken-ichi Yamada

  DOI：10.1039/d3ob01895d

  日期：——

  We developed a novel thiourea Lewis-base catalyst with phenol moieties for the enantioselective 5-exo-bromolactonization of stilbenecarboxylic acids to afford chiral 3-substituted phthalides. The phenol moieties are crucial for the enantio- and regio-selectivity.

  我们开发了一种带有苯酚部分的新型硫脲路易斯碱催化剂，用于二苯乙烯甲酸的对映选择性 5-外型-溴内酯化反应，得到手性 3-取代的苯并呋喃酮。苯酚部分对于对映体和区域选择性至关重要。