(Z)-3-[3,5-bis(trifluoromethyl)phenyl]acrylic acid | 1340475-16-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-3-[3,5-bis(trifluoromethyl)phenyl]acrylic acid
• 英文别名: (Z)-3-[3,5-Bis(trifluoromethyl)phenyl]propenoic acid；(Z)-3-[3,5-bis(trifluoromethyl)phenyl]prop-2-enoic acid
• CAS: 1340475-16-2
• 化学式: C₁₁H₆F₆O₂
• 分子量: 284.158
• InChiKey: IZKCKOPHMWHBHR-UPHRSURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (Z)-3-[3,5-bis(trifluoromethyl)phenyl]acrylic acid 、 (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(3-methoxypyridin-2-yl)oxyoxane-3,4,5-triol 以 甲苯 为溶剂， 反应 8.0h， 以98%的产率得到(Z)-(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl 3-[3,5-bis(trifluoromethyl)phenyl]acrylate
  参考文献：
  名称：

  使用未保护的糖基供体立体选择性合成顺式肉桂酸β-糖基酯及其衍生物

  摘要：

  使用Hannesian未保护的糖基供体和甲苯中的羧酸，直接合成了顺式肉桂酸的β-糖基酯。该方案不需要糖基供体上的保护基，并且实现了高立体选择性。还描述了有效的化感化学物质1 - O-顺式-肉桂酰基-β-d-吡喃葡萄糖的首次合成。

  DOI：

  10.1016/j.tetlet.2011.08.104
• 作为产物：
  描述：

  ethyl 3-(3,5-bis(trifluoromethyl)phenyl)acrylate 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以93%的产率得到(Z)-3-[3,5-bis(trifluoromethyl)phenyl]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