4-(allyloxy)-3-hydroxybenzaldehyde | 79822-65-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(allyloxy)-3-hydroxybenzaldehyde
• 英文别名: 3-hydroxy-4-(2-propenyloxy)benzaldehyde；4-Allyloxy-3-hydroxybenzaldehyde；3-hydroxy-4-prop-2-enoxybenzaldehyde
• CAS: 79822-65-4
• 化学式: C₁₀H₁₀O₃
• mdl: MFCD09033660
• 分子量: 178.188
• InChiKey: VFZJBQLCKIEHJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  4
• 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：

  4-(allyloxy)-3-hydroxybenzaldehyde 反应 2.0h， 以89%的产率得到3,4-dihydroxy-5-(prop-2-enyl)benzaldehyde
  参考文献：
  名称：

  Synthesis of ring-alkylated isoproterenol derivatives

  摘要：

  DOI：

  10.1021/jo00337a007
• 作为产物：
  描述：

  4-allyloxy-3-((2-(trimethylsilyl)ethoxy)methoxy)benzaldehyde 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以65%的产率得到4-(allyloxy)-3-hydroxybenzaldehyde
  参考文献：
  名称：

  [EN] INHIBITORS OF BACTERIAL BIOFILM FORMATION
  [FR] INHIBITEURS DE LA FORMATION DE BIOFILM BACTÉRIEN

  摘要：

  有机化合物被描述为用于抑制或预防细菌生物膜的形成。

  公开号：

  WO2009142720A1

文献信息

• Towards the development of a covalently tethered MALDI system — A study of allyl-modified MALDI matrixes
  作者：Sanela Martic、John D Brennan、Michael A Brook、Suzanne Ackloo、Noemi Nagy

  DOI：10.1139/v06-185

  日期：2007.1.1

  An emerging application of matrix-assisted laser desorption ionization (MALDI) mass spectrometry is the analysis of low molecular weight (LMW) compounds, often via coupled liquid chromatography — MALDI-MS methods. However, in many cases, the low molecular weight region of MALDI mass spectra is obscured by the presence of signals originating from the matrix, suggesting that the development of tethered MALDI matrixes may be required to optimize MS performance for such compounds. To gain insight into potential sites for covalent attachment of MALDI matrixes, we have systematically investigated the role played by a variety of functional group motifs in determining matrix efficiency for three common MALDI matrixes, as judged both by total signal intensity and background noise from matrix decomposition for a set of LMW compounds. A series of allyl derivatives of standard matrixes was prepared, and the efficiency of these materials in the MALDI experiment was measured. All modifications of established matrixes, e.g., 2,5-dihydroxybenzoic acid (DHB), α-cyano-4-hydroxycinnamic acid (CHCA), and caffeic acid (CA), or close analogues led to decreased absolute signal intensity and signal-to-background levels. Improved performance was generally observed with (i) the presence of a phenolic group (carboxylic acids were less effective) (ii) crystalline derivatives, and (iii) compounds that had high extinction coefficients at wavelengths near to that of the exciting laser (337 nm). The most interesting derivatives were the O-allyl ether (15) and N-allyl amide (16) of caffeic acid. These compounds did not facilitate signals from all four analytes tested. However, the observed spectra contained fewer signals from the matrix than from the parent compound CA. These compounds demonstrate that functionalization of MALDI matrixes, ultimately leading to tethered matrixes, is possible without jeopardizing signal intensity.Key words: MALDI, protected matrix, phenol, caffeic acid, allyl ether.

  基质辅助激光解吸电离（MALDI）质谱的一个新兴应用是分析低分子量（LMW）化合物，通常采用液相色谱-MALDI-MS 联用方法。然而，在许多情况下，MALDI 质谱的低分子量区域会因基质信号的存在而变得模糊不清，这表明可能需要开发系留 MALDI 基质，以优化此类化合物的质谱性能。为了深入了解共价附着 MALDI 基质的潜在位点，我们系统地研究了各种官能团基团在决定三种常见 MALDI 基质的基质效率方面所起的作用，这些作用是通过一组低分子量化合物的总信号强度和基质分解产生的背景噪声来判断的。我们制备了一系列标准基质的烯丙基衍生物，并测量了这些材料在 MALDI 实验中的效率。对 2,5-二羟基苯甲酸 (DHB)、α-氰基-4-羟基肉桂酸 (CHCA) 和咖啡酸 (CA) 等既定基质或近似物的所有改性都会导致绝对信号强度和信号-背景水平的降低。一般来说，(i) 含有酚基（羧酸的效果较差）(ii) 结晶衍生物，以及 (iii) 在接近激发激光波长（337 纳米）时消光系数较高的化合物，其性能会有所改善。最有趣的衍生物是咖啡酸的 O-烯丙基醚（15）和 N-烯丙基酰胺（16）。这些化合物并没有促进所有四种测试分析物发出信号。不过，观察到的光谱中来自基质的信号少于来自母体化合物 CA 的信号。这些化合物表明，在不影响信号强度的情况下，对 MALDI 基质进行功能化，最终形成系留基质是可能的：MALDI、保护基质、苯酚、咖啡酸、烯丙基醚。
• Synthesis of a Photo-Caged DOPA Derivative by Selective Alkylation of 3,4-Dihydroxybenzaldehyde
  作者：Tobias Schneider、Vladimir Kubyshkin、Nediljko Budisa

  DOI：10.1002/ejoc.201701749

  日期：2018.5.15

  A general route towards 3‐O‐alkylated DOPA derivatives has been developed. The regioselectivity of the synthesis was controlled by the number of base equivalents in the first alkylation step. In this way a photo‐caged DOPA was prepared that can readily be incorporated into recombinant protein sequences, thus enabling biosynthetic production of light‐activatable bioadhesives.

  已经开发了一种制备3-O-烷基化DOPA衍生物的一般方法。合成的区域选择性由第一烷基化步骤中碱当量的数量控制。这样，制备了光笼装的DOPA，可以将其轻松地掺入重组蛋白序列中，从而能够生物合成生产可光活化的生物粘合剂。
• Regioselective mono-O-alkylation of same pyrocatechoxide dianions
  作者：Satinder V. Kessar、Yash P. Gupta、Taj Mohammad、Manju Goyal、Kewal K. Sawal

  DOI：10.1039/c39830000400

  日期：——

  In dimethyl sulphoxide the dianions derived from 2,3- or 3,4-dihydroxybenzaldehydes and 4-methylesculetin afford products corresponding to alkylation at the less acidic site while the monoanions give the isomeric phenols.

  在二甲亚砜中，衍生自2,3-或3,4-二羟基苯甲醛和4-甲基七丁烯的二价阴离子在较低的酸性位点提供对应于烷基化的产物，而单阴离子给出异构体的苯酚。
• Ester derivatives as phosphodiesterase inhibitors
  申请人：CHIESI FARMACEUTICI S.p.A.

  公开号：EP2070913A1

  公开（公告）日：2009-06-17

  The invention relates to inhibitors of the phosphodiesterase 4 (PDE4) enzyme. More particularly, the invention relates to compounds that are new ester derivatives, methods of preparing such compounds, compositions containing them and therapeutic use thereof.

  该发明涉及磷酸二酯酶4（PDE4）酶的抑制剂。更具体地说，该发明涉及新的酯衍生物化合物，制备这些化合物的方法，含有它们的组合物以及它们的治疗用途。
• Regioselective Alkylation of Catechols via Mitsunobu Reactions
  作者：Xiaolong Wang、Tingting Ju、Xiaodong Li、Xiaoping Cao

  DOI：10.1055/s-0030-1259031

  日期：2010.12

  A mild and efficient Mitsunobu protocol for the regioselective alkylation of catechols such as 3,4-dihydroxybenzaldehyde and methyl 3,4-dihydroxybenzoate is described. The para-alkylation products could be easily prepared via the Mitsunobu reaction with high selectivity in moderate to good yields.

  描述了一种温和且高效的Mitsunobu协议，用于对儿茶酚类化合物（如3,4-二羟基苯甲醛和甲基3,4-二羟基苯甲酸酯）进行区域选择性烷基化。通过Mitsunobu反应，能够以较高选择性和中等到良好的产率轻松制备对位烷基化产物。