(Z)-ethyl 3-[(1,1'-biphenyl)-4-yl]acrylate | 1096026-88-8

• 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: (Z)-ethyl 3-[(1,1'-biphenyl)-4-yl]acrylate
• 英文别名: (Z)-ethyl 3-([1,1′-biphenyl]-4-yl)acrylate；ethyl 3-([1,1′-biphenyl]-4-yl)acrylate；ethyl (Z)-3-(4-phenylphenyl)prop-2-enoate
• CAS: 1096026-88-8
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: LYNHIVQASBBHFQ-RAXLEYEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  5
• 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：

  (Z)-ethyl 3-[(1,1'-biphenyl)-4-yl]acrylate 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以96%的产率得到(Z)-3-[(1,1'-biphenyl)-4-yl]acrylic acid
  参考文献：
  名称：

  Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors

  摘要：

  1-O-cis-Cinnamoyl-beta-D-glucopyranose is one of the most potent allelochemicals that has been isolated from Spiraea thunbergii Sieb by Hiradate et al. It derives its strong inhibitory activity from cis-cinnamic acid (cis-CA), which is crucial for phytotoxicity. By preparing and assaying a series of cis-CA analogues, it was previously found that the key features of cis-CA for lettuce root growth inhibition are a phenyl ring, cis-configuration of the alkene moiety, and carboxylic acid. On the basis of a structure-activity relationship study, the substituent effects on the aromatic ring of cis-CA were examined by systematic synthesis and the lettuce root growth inhibition assay of a series of cis-CA analogues having substituents on the aromatic ring. While ortho- and para-substituted analogues exhibited low potency in most cases, meta-substitution was not critical for potency, and analogues having a hydrophobic and sterically small substituent were more likely to be potent. Finally, several cis-CA analogues were found to be more potent root growth inhibitors than cis-CA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.08.013
• 作为产物：
  描述：

  对苯基苯甲醛 、 ethyl 2-[bis(2-isopropylphenoxy)phosphoryl]acetate 在 苄基三甲基氢氧化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以86%的产率得到(Z)-ethyl 3-[(1,1'-biphenyl)-4-yl]acrylate
  参考文献：
  名称：

  Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors

  摘要：

  1-O-cis-Cinnamoyl-beta-D-glucopyranose is one of the most potent allelochemicals that has been isolated from Spiraea thunbergii Sieb by Hiradate et al. It derives its strong inhibitory activity from cis-cinnamic acid (cis-CA), which is crucial for phytotoxicity. By preparing and assaying a series of cis-CA analogues, it was previously found that the key features of cis-CA for lettuce root growth inhibition are a phenyl ring, cis-configuration of the alkene moiety, and carboxylic acid. On the basis of a structure-activity relationship study, the substituent effects on the aromatic ring of cis-CA were examined by systematic synthesis and the lettuce root growth inhibition assay of a series of cis-CA analogues having substituents on the aromatic ring. While ortho- and para-substituted analogues exhibited low potency in most cases, meta-substitution was not critical for potency, and analogues having a hydrophobic and sterically small substituent were more likely to be potent. Finally, several cis-CA analogues were found to be more potent root growth inhibitors than cis-CA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.08.013

文献信息

• Silver-Catalyzed Cross-Olefination of Donor and Acceptor Diazo Compounds: Use of<i>N</i>-Nosylhydrazones as Diazo Surrogate
  作者：Zhaohong Liu、Binbin Liu、Xue-Feng Zhao、Yan-Bo Wu、Xihe Bi

  DOI：10.1002/ejoc.201601610

  日期：2017.1.26

  The cross-olefination reaction of donor and acceptor diazo compounds is reported. The use of N-nosylhydrazones as the diazo surrogates and the dependence on silver catalysis are crucial for the reaction development. A variety of (hetero)aryl N-nosylhydrazones and α-diazo esters, amides, and phosphonates were compatible, affording functionalized alkenes in good-to-high yields with moderate Z/E selectivity

  报道了供体和受体重氮化合物的交叉烯烃化反应。使用 N-nosylhydrazones 作为重氮替代物和对银催化的依赖对于反应发展至关重要。各种（杂）芳基 N-nosylhydrazones 和 α-重氮酯、酰胺和膦酸酯是相容的，以良好到高的产率提供功能化烯烃，Z/E 选择性适中。实验和 DFT 计算结果表明交叉选择性是由于银催化剂对供体重氮化合物的选择性活化。
• BF₃·OEt₂-mediated syn-selective Meyer–Schuster rearrangement of phenoxy propargyl alcohols for Z-β-aryl-α,β-unsaturated esters
  作者：Surendra Puri、Madala Hari Babu、Maddi Sridhar Reddy

  DOI：10.1039/c6ob01090c

  日期：——

  1-aryl-3-phenoxy propargyl alcohols is achieved via a BF3-mediated syn-selective Meyer–Schuster rearrangement under ambient conditions. The reaction mechanism is postulated to involve an electrophilic borylation of an allene intermediate as the key step to kinetically control the stereoselectivity.

  通过在环境条件下通过BF 3介导的顺选择性Meyer-Schuster重排，可以从容易获得的1-芳基-3-苯氧基炔丙基醇合成Z -β-芳基-α，β-不饱和酯。假定该反应机理涉及丙二烯中间体的亲电子硼化，这是动力学控制立体选择性的关键步骤。
• Novel Fused Arylpyrimidinone Based Allosteric Modulators of the M₁ Muscarinic Acetylcholine Receptor
  作者：Shailesh N. Mistry、Herman Lim、Manuela Jörg、Ben Capuano、Arthur Christopoulos、J. Robert Lane、Peter J. Scammells

  DOI：10.1021/acschemneuro.6b00018

  日期：2016.5.18

  the addition of either one or two methyl groups in the 7- and/or 8-position of the quinazolin-4(3H)-one core. These results demonstrate that the tricyclic benzo[h]quinazolin-4(3H)-one core could be replaced with a quinazolin-4(3H)-one core and maintain functional affinity. As such, the quinazolin-4(3H)-one core represents a novel scaffold to further explore M1 mAChR PAMs with improved physicochemical

  Benzoquinazolinone 1是M的正变构调节剂（PAM）1毒蕈碱乙酰胆碱受体（的mAChR），这是比显著原型PAM更有效，1-（4-甲氧基苄基）-4-氧代-1,4-二氢喹啉-3- -羧酸（BQCA）。在这项研究中，我们探讨了结构决定因素，这些决定因素是1作为M 1 mAChR的PAM活性的基础。我们特别注意了化合物1的三环支架的重要性，用于分子的活性。外围稠合苯环的完全缺失导致与乙酰胆碱（ACh）的亲和力和结合协同作用显着降低。通过在喹唑啉-4（3H）-一个核心的7和/或8位添加一个或两个甲基来挽救这种亲和力的丧失。这些结果表明，该三环苯并[ ħ ]喹唑啉-4（3 H ^） -酮芯可以与喹唑啉-4（3代替ħ） -酮芯和保持功能性亲和力。这样，喹唑啉-4（3 H）一核代表了一种新型支架，可以进一步探索具有改善的理化性质的M 1 mAChR PAM。