4-(1-hydroxyethyl)-2,6-dimethoxyphenol | 33900-62-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(1-hydroxyethyl)-2,6-dimethoxyphenol
• CAS: 33900-62-8
• 化学式: C₁₀H₁₄O₄
• mdl: MFCD00238585
• 分子量: 198.219
• InChiKey: DDDDTTULEBRRJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  336.0±42.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)
• 保留指数：
  1661.5

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2909500000
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  4-(1-hydroxyethyl)-2,6-dimethoxyphenol 在 硝酸 、 sodium nitrite 作用下， 以 甲醇 为溶剂， 以56%的产率得到2,6-二甲氧基-1,4-苯醌
  参考文献：
  名称：

  二氧化氮和氧气催化对位取代苯酚的催化氧化

  摘要：

  在O 2的甲醇溶液中，以催化量的NO 2将一系列对位取代的苯酚以中等至高收率氧化为相应的苯醌。在氩气下观察到很少或没有氧化。当用化学计量的CCl 4中的NO 2处理时，较低反应性的底物产生醌，但芳环的硝化成为重要的副产物。

  DOI：

  10.1016/s0040-4039(98)00242-1
• 作为产物：
  描述：

  乙酰丁香酮 在 sodium tetrahydroborate 作用下， 生成 4-(1-hydroxyethyl)-2,6-dimethoxyphenol
  参考文献：
  名称：

  Fourier transform Raman assignment of guaiacyl and syringyl marker bands for lignin determination

  摘要：

  A near infrared fourier transform Raman (NIR-FTR) spectroscopic technique was utilized to characterize lignin in wood. The Raman bands for C=C stretching derived from 4-hydroxy-3-methoxyphenyl (guaiacyl) nuclei and from 3,5-dimethoxy-4-hydroxyphenyl (syringyl) nuclei exist independently. The NIR-FTR analysis of a series of lignin model compounds indicated that a syringyl band was shifted to a lower frequency compared to a guaiacyl band. This shift was also observed in chemically synthesized lignin (DHP). Syringyl DHP, in which all the aromatic nuclei consist of syringyl type, exhibited a C=C stretching band at 1594 cm(-1), while guaiacyl DHP exhibited the band at 1599 cm(-1). These bands were designated as syringyl and guaiacyl marker bands, respectively. Chemical and physical treatment of hardwood and softwood exhibited different characteristics. One of the reasons is the chemical structure of lignin. Softwood mainly contains only guaiacyl lignin, while hardwood contains both guaiacyl and syringyl lignin, and the syringyl/guaiacyl (S/G) ratio varies among species. Under high-resolution conditions (1 cm(-1)), the NIR-FTR spectra of 10 hardwoods (wood meal samples) revealed that both syringyl and guaiacyl marker bands existed. On the other hand, the spectra of softwoods contained only a guaiacyl marker bands existed. On the other hand, the spectra of softwoods contained only a guaiacyl marker band. The S/G ratio in hardwood calculated from the peak area intensity ratio of two marker bands shows a linear relationship with the SIG ratio obtained from conventional nitrobenzene oxidation analysis with the correlation factor>0.96. Furthermore, if peak component separation analysis was combined, low-resolution spectral data gave a similar S/G ratio. Either syringyl of guaiacyl marker bands can be assigned in the NIR-FTR spectra of wood blocks (saw-cut surface). This spectral technique may provide an easy-handling and non-destructive analytical method for lignin determination. (C) 1997 Elsevier Science B.V.

  DOI：

  10.1016/s1386-1425(97)00100-5
• 作为试剂：
  描述：

  methyl (E)-sinapate 在 吡啶 、 4-(1-hydroxyethyl)-2,6-dimethoxyphenol 、 水 、 双氧水 、 对甲苯磺酸 、 horseradish peroxidase EC 1.11.1.7 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 22.0h， 生成 Methyl 3-hydroxy-2,3-bis(4-hydroxy-3,5-dimethoxyphenyl)propanoate peracetate
  参考文献：
  名称：

  Setaela, Harri; Pajunen, Aarne; Rummakko, Petteri, Journal of the Chemical Society. Perkin transactions I, 1999, # 4, p. 461 - 464

  摘要：

  DOI：

文献信息

• Cu(OAc)₂-catalyzed remote benzylic C(sp³)–H oxyfunctionalization for CO formation directed by the hindered para-hydroxyl group with ambient air as the terminal oxidant under ligand- and additive-free conditions
  作者：Jian-An Jiang、Cheng Chen、Jian-Gang Huang、Hong-Wei Liu、Song Cao、Ya-Fei Ji

  DOI：10.1039/c3gc41946k

  日期：——

  A hindered para-hydroxyl group-directed remote benzylic C(sp3)–H oxyfunctionalization has been developed for the straightforward transformation of 2,6-disubstituted 4-cresols, 4-alkylphenols, 4-hydroxybenzyl alcohols and 4-hydroxybenzyl alkyl ethers into various aromatic carbonyl compounds. The ligand- and additive-free Cu(OAc)2-catalyzed atmospheric oxidation mediated by ethylene glycol unlocks a

  已经开发了一种受阻的对羟基定向的远程苄基C（sp 3）–H氧官能团，用于将2,6-二取代的4-甲酚，4-烷基苯酚，4-羟基苄醇和4-羟基苄基烷基醚直接转化为各种芳族羰基化合物。由乙二醇介导的无配体和无添加剂的Cu（OAc）2催化的大气氧化作用，可以使伯苄基和仲苄基官能化，形成简便，原子经济且对环境无害的C O形成。由于4-羟基苯甲醛和4-羟基苯酮的药物重要性，因此该方法对于基础研究和实际应用均具有重要价值。
• Photoacid-Enabled Synthesis of Indanes via Formal [3 + 2] Cycloaddition of Benzyl Alcohols with Olefins
  作者：Biao Yang、Kui Dong、Xiang-Sheng Li、Li-Zhu Wu、Qiang Liu

  DOI：10.1021/acs.orglett.2c00566

  日期：2022.3.18

  photoacid system containing catalytic protonated merocyanine (MEH). Under visible-light irradiation, MEH yields a metastable spiro structure and liberated protons, which facilitates the formation of carbocations from benzyl alcohols, thus delivering diverse molecules in the presence of various nucleophiles. Mainly, a variety of indanes could be easily obtained from benzyl alcohols and olefins, and water

  通过含有催化质子化部花青 (MEH) 的亚稳态光酸体系，开发了一种环境友好且高度非对映选择性合成茚满的方法。在可见光照射下，MEH 产生亚稳态螺结构并释放质子，这有助于从苯甲醇中形成碳正离子，从而在各种亲核试剂存在下传递多种分子。主要是从苯甲醇和烯烃中很容易得到多种茚满烷，而水是唯一的副产物。
• A facile tandem double-dehydrative-double-Heck olefination strategy for pot-economic synthesis of ( E )-distyrylbenzenes as multi-target-directed ligands against Alzheimer's disease employing C. elegans model
  作者：Nitin H. Andhare、Yogesh Thopate、Shamsuzzama、Lalit Kumar、Tanuj Sharma、M.I. Siddiqi、Arun K. Sinha、Aamir Nazir

  DOI：10.1016/j.tet.2018.02.026

  日期：2018.4

  one pot and regioselective access to (E)-distyrylbenzenes (DSBs) from arylhalide and secondary phenylenediethanol, a stable precursor for in situ generation of divinylbenzene (DVB) to avoid its polymerization, is described for construction of double CC bond formation via tandem double-dehydrative-double-Heck (D-D-D-H) reaction using Palladium and ionic liquid [hmim]Br as a cooperative catalyst. It

  描述了一种简明的，一锅的和区域选择性的从芳基卤化物和仲苯二乙醇（一种原位生成二乙烯基苯（DVB）以避免聚合反应的稳定前体）进入（E）-二苯乙烯基苯（DSB）的方法，用于构造双C C键形成通过钯和离子液体[hmim] Br作为协同催化剂的串联双脱水双赫克（DDDH）反应。值得注意的是，这种罐经济方法还可以直接合成羟基化的二苯乙烯基苯，而无需保护-脱保护策略。重要的是，要测试合成的DSB对β的保护活性在发现1,3-双（（E）-4-（三氟甲基）苯乙烯基）苯（5c）具有活性的转基因秀丽隐杆线虫模型中，淀粉样蛋白还原，乙酰胆碱酯酶抑制，脂质降低和活性氧（ROS）降低特性跨所有上述因素，从而在多目标定向配体（MTDLs）方法中展示了先导分子。还进行了分子对接研究，以了解有效的DSB与受体之间的相互作用。
• Thiol-Ene “Click” Reaction Triggered by Neutral Ionic Liquid: The “Ambiphilic” Character of [hmim]Br in the Regioselective Nucleophilic Hydrothiolation
  作者：Rajesh Kumar、Saima、Amit Shard、Nitin H. Andhare、Richa、Arun K. Sinha

  DOI：10.1002/anie.201408721

  日期：2015.1.12

  the “ambiphilic” character of the ionic liquid promotes the nucleophilic addition of thiol to styrene through an anti‐Markovnikov pathway. The catalyst recyclability and the extension of the methodology for thiol–yne click chemistry are additional benefits. A competitive study among thiophenol, styrene, and phenyl acetylene revealed that the rate of reaction is in the order of thiol–yne>thiol–ene>dimerization

  硫醇-“咔嗒”化学已成为构建碳-杂原子（CS）键的有力策略，通常会形成两个区域异构体。为此，已经探索了中性离子液体[hmim] Br作为溶剂兼催化剂，用于从活化和失活的苯乙烯衍生物或仲苄醇和硫醇合成线性硫醚，而无需使用金属络合物，碱或自由基引发剂。此外，使用1进行详细的机械研究1 H NMR光谱和四极杆飞行时间电喷雾电离质谱（Q-TOF ESI-MS）表明，离子液体的“两亲”特性通过反马尔可夫尼科夫途径促进了巯基与苯乙烯的亲核加成。催化剂的可回收性和硫醇-炔点击化学方法的扩展是其他好处。硫酚，苯乙烯和苯基乙炔之间的竞争研究表明，反应速率为[hmim] Br中的硫醇-炔>硫醇-烯>硫醇二聚的顺序。
• A Chemoselective, Easy Bromination of (Hydroxymethyl)phenols
  作者：Lidia De Luca、Giammario Nieddu、Giampaolo Giacomelli

  DOI：10.1055/s-0028-1083247

  日期：2008.12

  A simple and chemoselective method for direct bromination of (hydroxymethyl)phenols via reaction with 2,4,6-trichloro[1,3,5]triazine in N,N -dimethylformamide at room temperature is described. The reaction occurs without affecting the phenolic hydroxy group.

  描述了一种在室温下与 N,N-二甲基甲酰胺中的 2,4,6-三氯[1,3,5]三嗪反应直接溴化（羟甲基）苯酚的简单化学选择性方法。该反应在不影响酚羟基的情况下发生。