3-acetoxy-2-hydroxybenzaldehyde | 55477-54-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 3-acetoxy-2-hydroxybenzaldehyde
• 英文别名: (3-Formyl-2-hydroxyphenyl) acetate
• CAS: 55477-54-8
• 化学式: C₉H₈O₄
• 分子量: 180.16
• InChiKey: ODCGBUMUKBQFKA-UHFFFAOYSA-N

物化性质

• 沸点：
  270.0±30.0 °C(Predicted)
• 密度：
  1.313±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-acetoxy-2-hydroxybenzaldehyde 在 硫酸 、 硝酸 、 溶剂黄146 作用下， 以61%的产率得到3-acetoxy-2-hydroxy-5-nitrobenzaldehyde
  参考文献：
  名称：

  Mechanophore-Linked Addition Polymers

  摘要：

  The use of mechanical energy to increase reaction rates and alter the distribution of products has gained considerable interest of late. However, the discovery of new mechanophores (i.e., mechanochemically reactive units) is currently time-consuming, expensive, low-yielding, and a process that is not easily scaled to large quantities. Here we show that mechanophore-linked addition polymers are easily prepared using bifunctional initiators with a living radical polymerization method. The mechanophore is positioned close to the center of the polymer, where ultrasound-generated forces are the largest. Since these forces are strongly dependent on molecular weight, the use of controlled polymerization enables fine-tuning of the mechanical activity so that mechanophore reactions are initiated while minimizing chain scission. The approach is illustrated first with the synthesis and investigation of a 1,2-disubstituted benzocyclobutene mechanophore that is incorporated into the center of a polymethacrylate (PMA) chain. Selected molecular weights are probed using ultrasound to illustrate that the 4 pi electrocyclic ring opening of the benzocyclobutene link is stress-induced. To demonstrate the broad applicability of this method for mechanophore screening, we also report a new spiropyran-linked PMA that undergoes an ultrasound-induced 6 pi-electron electrocyclic ring opening. The straightforward synthesis of mechanophore-linked addition polymers presented here shows considerable promise for the investigation of new mechanophores and will lead to a greater understanding of mechanochemical reactivity within polymer systems.

  DOI：

  10.1021/ja076189x
• 作为产物：
  描述：

  2,3-二羟基苯甲醛 、 乙酸酐 以 溶剂黄146 为溶剂， 反应 72.0h， 以76%的产率得到3-acetoxy-2-hydroxybenzaldehyde
  参考文献：
  名称：

  Metathesis catalysts

  摘要：

  该发明涉及聚合物过渡金属催化剂，涉及制备这些催化剂的方法，涉及中间体，以及涉及将过渡金属催化剂用作有机反应中的催化剂，特别是在烯烃重排反应中的用途。

  公开号：

  US20080139861A1

文献信息

• Study of Coumarin-Resveratrol Hybrids as Potent Antioxidant Compounds
  作者：Maria Matos、Francisco Mura、Saleta Vazquez-Rodriguez、Fernanda Borges、Lourdes Santana、Eugenio Uriarte、Claudio Olea-Azar

  DOI：10.3390/molecules20023290

  日期：——

  In the present work we synthesized a selected series of hydroxylated 3-phenylcoumarins 5–8, with the aim of evaluating in detail their antioxidant properties. From an in depth study of the antioxidant capacity data (ORAC-FL, ESR, CV and ROS inhibition) it was concluded that these derivatives are very good antioxidants, with very interesting profiles in all the performed assays. The study of the effect of the number and position of the hydroxyl groups on the antioxidant activity was the principal aim of this study. In particular, 7-hydroxy-3-(3'-hydroxy)phenylcoumarin (8) proved to be the most active and effective antioxidant of the selected series in four of the performed assays (ORAC-FL = 11.8, capacity of scavenging hydroxyl radicals = 54%, Trolox index = 2.33 and AI30 index = 0.18). However, the presence of two hydroxyl groups on this molecule did not increase greatly the activity profile. Theoretical evaluation of ADME properties of all the derivatives was also carried out. All the compounds can act as potential candidates for preventing or minimizing the free radical overproduction in oxidative-stress related diseases. These preliminary findings encourage us to perform a future structural optimization of this family of compounds.

  在本研究中，我们合成了一系列选择性的羟基化3-苯基香豆素5-8，旨在详细评估其抗氧化特性。通过对抗氧化能力数据（ORAC-FL、ESR、CV和ROS抑制）的深入研究，我们得出结论，这些衍生物是非常好的抗氧化剂，在所有进行的实验中表现出非常有趣的特征。研究羟基数量和位置对抗氧化活性的影响是本研究的主要目标。特别是，7-羟基-3-(3'-羟基)苯基香豆素（8）被证明是所选系列中在四项实验中最活跃和有效的抗氧化剂（ORAC-FL=11.8，羟基自由基清除能力=54%，Trolox指数=2.33，AI30指数=0.18）。然而，这种分子上两个羟基的存在并没有显著提高活性特征。还对所有衍生物的ADME特性进行了理论评估。所有化合物都可以作为潜在候选者，以防止或减少与氧化应激相关疾病中自由基的过量产生。这些初步发现鼓励我们对这一类化合物进行未来的结构优化。
• Lipase-catalyzed regioselective protection of hydroxyl groups in aromatic dihydroxyaldehydes and ketones
  作者：Giovanni Nicolisi、Mario Piattelli、Claudia Sanfilippo

  DOI：10.1016/s0040-4020(01)89897-5

  日期：1993.4

  Pseudomonas cepacia lipase catalyzes the acetylation in organic solvent of dihydroxyaldehydes and ketones using vinyl acetate as acyl donor. The method is completely regioselective and allows to obtain partially acetylated compounds different from those obtained by enzymic hydrolysis of polyacetoxy arylaldehydes and ketones.

  假单胞菌洋葱脂肪酶在乙酸乙烯酯作为酰基供体的情况下催化二羟基醛和酮在有机溶剂中的乙酰化。该方法是完全区域选择性的，并允许获得部分乙酰化的化合物，该化合物与通过酶水解聚乙酰氧基芳基醛和酮获得的化合物不同。
• Synthesis of Imidazolium-Tagged Ruthenium Carbene Complex: Remarkable Activity and Reusability in Regard to Olefin Metathesis in Ionic Liquids
  作者：Hideaki Wakamatsu、Yuri Saito、Masami Masubuchi、Reiko Fujita

  DOI：10.1055/s-2008-1077888

  日期：——

  We have demonstrated the synthesis of a new ionic liquid supported ruthenium carbene complex la,b and its applications to olefin metathesis. These catalysts can be used for ring-closing metathesis in the construction of five-to-eight-membered rings with high activity and good recyclability.

  我们已经展示了一种新的离子液体负载的钌卡宾配合物 la,b 的合成及其在烯烃复分解中的应用。这些催化剂可用于闭环复分解，构建五至八元环，具有高活性和良好的可回收性。
• LIGHT-EMITTING ORGANIC PLATINUM COMPLEX, LIGHT-EMITTING MATERIAL CONTAINING THIS COMPLEX AND FUNCTIONAL DEVICE
  申请人：Naota Takeshi

  公开号：US20130001535A1

  公开（公告）日：2013-01-03

  The present invention provides a light-emitting organic platinum complex, a light-emitting material containing this complex, and a functional device containing this complex. The light-emitting organic platinum complex is represented by any one of the following structural formulae: where: Z represents either —(CH 2 ) n — or —CH 2 (CH 2 OCH 2 ) m CH 2 —, where n represents 7 to 14, and m represents 3 to 4; A represents either an optionally condensed aromatic hydrocarbon ring or an optionally condensed heteroaromatic ring; R is a substituent group for A and represents H (unless n of Z in the structural formula (1) is 7 to 13), a halogen, a C 1 -C 6 alkyl group, a C 1 -C 6 alkenyl group, a C 1 -C 6 alkynyl group, a C 1 -C 6 alkoxy group or the like.

  本发明提供了一种发光的有机铂配合物，含有该配合物的发光材料以及含有该配合物的功能性器件。该发光的有机铂配合物由以下结构式之一表示：其中：Z代表—(CH2)n—或—CH2(CH2OCH2)mCH2—，其中n为7至14，m为3至4；A代表可选的紧邻芳香烃环或可选的紧邻杂芳烃环；R是A的取代基，表示H（除非结构式（1）中Z的n为7至13），卤素，C1-C6烷基，C1-C6烯基，C1-C6炔基，C1-C6烷氧基或类似物。
• Inhibitory Activity of 4-Benzylidene Oxazolones Derivatives of Cinnamic Acid on Human Acetylcholinesterase and Cognitive Improvements in a Mouse Model
  作者：Alma Marisol Ramírez-Ruiz、Martha Elena Ávila-Cossío、Arturo Estolano-Cobián、José Manuel Cornejo-Bravo、Ana Laura Martinez、Iván Córdova-Guerrero、Bibiana Roselly Cota-Ramírez、Krysta Paola Carranza-Ambriz、Ignacio A. Rivero、Aracely Serrano-Medina

  DOI：10.3390/molecules28217392

  日期：——

  (4H)-ones derivatives of cinnamic acid and evaluated the ability of these compounds to inhibit human acetylcholinesterase (hAChE). The most potent compound was evaluated for cognitive improvement in short-term memory. The seven compounds reversibly inhibited the hAChE between 51 and 75% at 300 μM, showed an affinity (Ki) from 2 to 198 μM, and an IC50 from 9 to 246 μM. Molecular docking studies revealed

  我们合成了七种肉桂酸的 (Z)-亚苄基-2-(E)-苯乙烯基恶唑-5(4H)-酮衍生物，并评估了这些化合物抑制人乙酰胆碱酯酶 (hAChE) 的能力。评估了最有效的化合物对短期记忆认知改善的效果。这七种化合物在 300 μM 浓度下可逆抑制 hAChE 51% 至 75%，亲和力 (Ki) 为 2 至 198 μM，IC50 为 9 至 246 μM。分子对接研究表明，所有化合物的所有结合部分都参与与 hAChE 的非共价相互作用。此外，还进行了计算机药代动力学分析以预测化合物的血脑屏障（BBB）渗透性。最有效的 hAChE 抑制剂在改良的 Y 迷宫测试 (5 μmol/kg) 和物体识别测试 (10 μmol/kg) 中显着改善认知障碍。我们的结果可以帮助合理设计 hAChE 抑制剂，使其成为治疗认知障碍的潜在候选药物。