(Z)-ethyl 3-[(1,1'-biphenyl)-2-yl]acrylate | 1499179-29-1

• 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)-2-yl]acrylate
• CAS: 1499179-29-1
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: HUTDYWVFZWNIOZ-SEYXRHQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 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：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (Z)-ethyl 3-[(1,1'-biphenyl)-2-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)-2-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：

  ethyl (E)-3-(2-biphenylyl)-2-propenoate 以 氘代氯仿 为溶剂， 反应 168.0h， 以25%的产率得到(Z)-ethyl 3-[(1,1'-biphenyl)-2-yl]acrylate
  参考文献：
  名称：

  邻位取代基促进了光诱导的E（反式）→Z（顺式）异构化

  摘要：

  在过去的几十年中，在C H活化和烯化反应中，邻位导向基团的快速增长。在本文中，我们以各种邻位取代基团的方式解决了这些烯化产物的光诱导的E  →  Z异构化。最初，我们发现邻苯并恶唑基芳基丙烯酸酯在365 nm直接辐射下有效地进行了E  →  Z异构化（产率高达88％）。此外，在C H活化和烯化反应中对其他5个导向基团进行研究发现，乙酰氨基基团也可以是增强E  →  Z的良好邻位取代基团。异构化。对照实验表明，取代位置对于光诱导的异构化或[2 + 2]环加成至关重要。最后，普遍有趣的荧光猝灭/变化现象总是伴随着异构化。X射线单晶法揭示了异构化过程对丙烯酸芳基酯片段进行了显着的共轭变形，我们认为这种变化可能有助于荧光和吸收剂的减少。

  DOI：

  10.1016/j.tetlet.2020.152396

文献信息

• Atom-economic threefold cross-couplings of triarylbismuth reagents with 2-halobenzaldehydes and pot-economic in situ Wittig functionalizations with phosphonium salts
  作者：Maddali L. N. Rao、Ritesh J. Dhanorkar

  DOI：10.1039/c4ra13348j

  日期：——

  In this paper we report an efficient pot-economic methodology for the synthesis of ortho-olefinated biaryls. This has been achieved through an atom-economic threefold cross-coupling of triarylbismuth reagents with 2-halobenzaldehydes followed by pot-economic in situ Wittig olefination. The overall process is a pot-economic straightforward synthesis of ortho-olefinated biaryls from 2-halobenzaldehydes, triarylbismuth reagents and phosphonium salts. This pot-economic approach was applied to the formal synthesis of medicinally important Eupomatilone-6.

  本文报道了一种高效的原位Wittig烯化反应方法，用于合成邻烯基联苯。通过三芳基铋试剂与2-卤代苯甲醛的三重交叉偶联，继而进行原位Wittig烯化，实现了这一目标。整个过程是从2-卤代苯甲醛、三芳基铋试剂和膦盐出发，高效简便地合成邻烯基联苯。这一方法已成功应用于重要的药用成分Eupomatilone-6的正式合成中。