(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

文献信息

• Substituent effects of cis-cinnamic acid analogues as plant growh inhibitors
  作者：Keisuke Nishikawa、Hiroshi Fukuda、Masato Abe、Kazunari Nakanishi、Tomoya Taniguchi、Takashi Nomura、Chihiro Yamaguchi、Syuntaro Hiradate、Yoshiharu Fujii、Katsuhiro Okuda、Mitsuru Shindo

  DOI：10.1016/j.phytochem.2013.08.013

  日期：2013.12

  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.
• Stereoselective synthesis of β-glycosyl esters of cis-cinnamic acid and its derivatives using unprotected glycosyl donors
  作者：Kazumasa Matsuo、Keisuke Nishikawa、Mitsuru Shindo

  DOI：10.1016/j.tetlet.2011.08.104

  日期：2011.10

  The β-glycosyl esters of cis-cinnamic acid were synthesized directly using Hannesian’s unprotected glycosyl donor and the carboxylic acid in toluene. This protocol does not require protecting groups on the glycosyl donors, and high stereoselectivity was achieved. The first synthesis of a potent allelochemical, 1-O-cis-cinnamoyl-β-d-glucopyranose, is also described.

  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。