间-(三氟甲基)-肉桂酸 | 16642-87-8

• 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
• 中文名称: 间-(三氟甲基)-肉桂酸
• 英文名称: (Z)-3-[3-(trifluoromethyl)phenyl]acrylic acid
• 英文别名: cis-m-Trifluormethyl-zimtsaeure；m-Trifluoromethyl cinnamic acid；(Z)-3-[3-(trifluoromethyl)phenyl]prop-2-enoic acid
• CAS: 16642-87-8
• 化学式: C₁₀H₇F₃O₂
• 分子量: 216.16
• InChiKey: KSBWHDDGWSYETA-PLNGDYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2916399090

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(Z)-ethyl 3-(3-(trifluoromethyl)phenyl)acrylate	1270893-40-7	C12H11F3O2	244.213

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(3-methoxypyridin-2-yl)oxyoxane-3,4,5-triol 、 间-(三氟甲基)-肉桂酸 以 甲苯 为溶剂， 反应 8.0h， 生成 (Z)-(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl 3-[3-(trifluoromethyl)phenyl]acrylate 、 (Z)-(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl 3-[3-(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：

  3-三氟甲基苯甲醛 在 水 、 苄基三甲基氢氧化铵 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 4.0h， 生成 间-(三氟甲基)-肉桂酸
  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

• MATRIX FOR MALDI MASS SPECTROMETRY AND MALDIMASS SPECTROMETRY METHOD
  申请人：Shindo Mitsuru

  公开号：US20140151548A1

  公开（公告）日：2014-06-05

  Provided is a matrix for MALDI mass spectrometry that has a high ability of ionizing low-molecular-weight compounds, and makes it possible to make measurement in a negative ion mode. The matrix is a matrix for mass spectrometry that contains one or more compounds selected from the group consisting of compounds each represented by the following general formula (I), (II) or (III), and their salts thereof. In the formulae (I), (II) and (III), X and Z are each C or N; R 1 and R 5 are each selected from the group consisting of H, an alkyl group, a (substituted) aryl group, a (substituted) arylalkyl group, and a (substituted) heteroaryl group; R 2 and R 6 are each selected from the group consisting of H, an alkyl group, an alkoxyl group, an amino group, a halogen atom, a nitro group, an allyl group, a (substituted) aryl group, and a (substituted) heteroaryl group; and R 7 and R 8 are each selected from the group consisting of H and an amino group provided that a case where R 1 =R 2 =H, and a case where R 7 =R 8 =an amino group are excluded.

  提供的是一种用于MALDI质谱的矩阵，具有高能力电离低分子量化合物的能力，并使得在负离子模式下进行测量成为可能。该矩阵是一种质谱矩阵，包含从由以下通式（I）、（II）或（III）表示的化合物组成的化合物中选择的一个或多个化合物及其盐。在式（I）、（II）和（III）中，X和Z分别为C或N；R1和R5分别选择自H、烷基、（取代）芳基、（取代）芳基烷基和（取代）杂芳基组成的群；R2和R6分别选择自H、烷基、烷氧基、氨基、卤素原子、硝基、烯丙基、（取代）芳基和（取代）杂芳基组成的群；R7和R8分别选择自H和氨基，但排除R1=R2=H和R7=R8=氨基的情况。
• MATRIX FOR MALDI MASS SPECTROMETRY
  申请人：Kyushu University National University Corporation

  公开号：EP2730918A1

  公开（公告）日：2014-05-14

  Provided is a matrix for MALDI mass spectrometry that has a high ability of ionizing low-molecular-weight compounds, and makes it possible to make measurement in a negative ion mode. The matrix is a matrix for mass spectrometry that contains one or more compounds selected from the group consisting of compounds each represented by the following general formula (I), (II) or (III), and their salts thereof. In the formulae (I), (II) and (III), X and Z are each C or N; R1 and R5 are each selected from the group consisting of H, an alkyl group, a (substituted) aryl group, a (substituted) arylalkyl group, and a (substituted) heteroaryl group; R2 and R6 are each selected from the group consisting of H, an alkyl group, an alkoxyl group, an amino group, a halogen atom, a nitro group, an allyl group, a (substituted) aryl group, and a (substituted) heteroaryl group; and R7 and R8 are each selected from the group consisting of H and an amino group provided that a case where R1 = R2 = H, and a case where R7 = R8 = an amino group are excluded.

  本发明提供了一种用于 MALDI 质谱分析的基质，该基质对低分子量化合物具有较高的电离能力，并可在负离子模式下进行测量。该基质是一种用于质谱分析的基质，含有一种或多种选自以下通式 (I)、(II) 或 (III) 所代表的化合物及其盐类的化合物。在式(I)、(II)和(III)中，X 和 Z 各自为 C 或 N；R1 和 R5 各自选自由 H、烷基、（取代的）芳基、（取代的）芳烷基和（取代的）杂芳基组成的组；R2和R6各自选自由H、烷基、烷氧基、氨基、卤素原子、硝基、烯丙基、（取代的）芳基和（取代的）杂芳基组成的组；以及R7和R8各自选自由H和氨基组成的组，但不包括R1＝R2＝H的情况和R7＝R8＝氨基的情况。
• 反式和顺式α,β不饱和羧酸的合成方法
  申请人：南方科技大学

  公开号：CN117700315A

  公开（公告）日：2024-03-15

  反式和顺式α,β不饱和羧酸的合成方法，涉及有机合成技术领域，其包括以烯基卤代物(I)和甲酸盐为原料，加入镍催化剂、光催化剂、联吡啶类配体和有机溶剂，在惰性气氛中，在蓝光照射下，室温下搅拌至反应完毕。本发明的方法反应条件温和，不需要氧化剂以及高温条件，同时避免了过渡金属的残留，从稳定易制备的各种烯基卤代物直接得到反式或顺式α,β不饱和羧酸化合物。
• MATRIX FOR MALDI MASS SPECTROMETRY AND MALDI MASS SPECTROMETRY METHOD
  申请人：Kyushu University, National University Corporation

  公开号：EP2730918B1

  公开（公告）日：2016-09-14
• 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.