cis-3-methoxycinnamic acid | 41397-74-4

• 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: cis-3-methoxycinnamic acid
• 英文别名: (Z)-3-(3-methoxyphenyl)acrylic acid；Z-3-methoxycinnamic acid；3-Methoxy-cis-zimtsaeure；m-Methoxyzimtsaeure；3-methoxy-cis-cinnamic acid；(Z)-3-(3-methoxyphenyl)prop-2-enoic acid
• CAS: 41397-74-4
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: LZPNXAULYJPXEH-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-3-methoxycinnamic acid 生成 3-Methoxycinnamic acid
  参考文献：
  名称：

  A suggestion to use dogs for detecting red palm weevil (Rhynchophorus ferrugineus) infestation in date palms in Israel

  摘要：

  DOI：

  10.1007/bf02981745
• 作为产物：
  描述：

  3-Methoxycinnamic acid 在 正丁胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 8.0h， 以77%的产率得到cis-3-methoxycinnamic acid
  参考文献：
  名称：

  了解质子离子液体（PIL）的作用和取代基作用，以增强Z-肉桂酸衍生物的生成。

  摘要：

  研究了MeCN中一系列取代的E-肉桂酸的酸形式及其相应的质子离子液体（PIL）在300 nm的光下的光异构化。研究了取代基的性质，强度，数量和位置对E-肉桂酸酯衍生物光化学行为的影响。还研究了在米氏酮存在下该反应的光敏化在366 nm的情况，这表明反应中涉及三重激发态。由于n的存在在所有情况下，形成PIL所需的丁胺都会显着提高光产物的产率，并讨论了PIL的作用。因此，对这些基本方面的理解已经使我们能够建立成功地合成Z-肉桂酸的优异且实用的合成方案。

  DOI：

  10.1039/d0pp00072h

文献信息

• Using non-covalent interactions to direct regioselective 2+2 photocycloaddition within a macrocyclic cavitand
  作者：Nga Nguyen、Aspen Rae Clements、Mahesh Pattabiraman

  DOI：10.1039/c5nj02376a

  日期：——

  completely from a head-to-head dimer to a head-to-tail dimer. The reactions were also stereoselective in most cases. Stoichiometry experiments were performed to explore relative stabilities of the complexes, which indicate that the ternary complex is more stable than others. Selectivity in the photocycloaddition reaction was also applied retrospectively to deduce intermolecular orientations. Time-dependent

  客体在三元包含复合物中的相对取向受主客体和客客体超分子相互作用的支配。可以使用非共价相互作用来控制大环空分子（γ-环糊精）中包含的两个烯烃之间的2 + 2光环加成反应的选择性。在此手稿中，我们报告了使用非共价相互作用的空泡蛋白介导的烷基肉桂酸酯之间区域选择性的控制。使用这种方法，我们已经表明区域选择性可以完全从头对头二聚体切换到头对尾二聚体。在大多数情况下，反应也是立体选择性的。进行了化学计量学实验以探索配合物的相对稳定性，这表明三元配合物比其他三元配合物更稳定。还追溯应用了光环加成反应中的选择性以推断分子间取向。我们进行的时间依赖性转换研究表明，所观察到的烯烃的反应性代表了复杂介质整体中的分子间取向。通过实验观察和计算研究来定性地了解复杂结构以及弱相互作用的相对强度。以淤浆形式研究了复合物的反应，反应控制的程度表明了类似固态的行为。通过实验观察和计算研究来定性地了解复杂结构以及弱相互作用
• 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.
• Templating Photodimerization of <i>trans</i>-Cinnamic Acids with Cucurbit[8]uril and γ-Cyclodextrin
  作者：Mahesh Pattabiraman、Arunkumar Natarajan、Lakshmi S. Kaanumalle、V. Ramamurthy

  DOI：10.1021/ol047866k

  日期：2005.2.1

  Cucurbit[8]uril and gamma-cyclodextrin are able to align two olefin molecules in a head-head fashion within their large cavities. Excitation of such templated olefins results in syn head-head cyclobutanes in nearly quantitative yields. The methodology revealed here works with transcinnamic acids that do not dimerize either in solution or in the solid state and with the ones that yield only anti head-tail dimer in the solid state.
• A suggestion to use dogs for detecting red palm weevil (Rhynchophorus ferrugineus) infestation in date palms in Israel
  作者：J. Nakash、Y. Osem、M. Kehat

  DOI：10.1007/bf02981745

  日期：2000.6
• Understanding the role played by protic ionic liquids (PILs) and the substituent effect for enhancing the generation of Z-cinnamic acid derivatives†
  作者：Rocío B. Rodríguez、Ramiro L. Zapata、María L. Salum、Rosa Erra-Balsells

  DOI：10.1039/d0pp00072h

  日期：2020.6

  Photoisomerization of a series of substituted E-cinnamic acids in MeCN in their acid forms and as their corresponding protic ionic liquids (PILs) with light of 300 nm is studied. The nature, strength, number, and position effects of substituents on the photochemical behavior of E-cinnamic derivatives are investigated. The photosensitization of the reaction in the presence of Michler's ketone is also

  研究了MeCN中一系列取代的E-肉桂酸的酸形式及其相应的质子离子液体（PIL）在300 nm的光下的光异构化。研究了取代基的性质，强度，数量和位置对E-肉桂酸酯衍生物光化学行为的影响。还研究了在米氏酮存在下该反应的光敏化在366 nm的情况，这表明反应中涉及三重激发态。由于n的存在在所有情况下，形成PIL所需的丁胺都会显着提高光产物的产率，并讨论了PIL的作用。因此，对这些基本方面的理解已经使我们能够建立成功地合成Z-肉桂酸的优异且实用的合成方案。