4-(2-hydroxyethyl)-2,6-dimethoxyphenol | 20824-45-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(2-hydroxyethyl)-2,6-dimethoxyphenol
• CAS: 20824-45-7
• 化学式: C₁₀H₁₄O₄
• mdl: MFCD24714264
• 分子量: 198.219
• InChiKey: BZMWVTKTSDHGBF-UHFFFAOYSA-N

物化性质

• 熔点：
  112-113 °C
• 沸点：
  349.9±37.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  4
• 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

反应信息

• 作为反应物：
  描述：

  4-(2-hydroxyethyl)-2,6-dimethoxyphenol 在 三溴化磷 作用下， 以 甲苯 为溶剂， 反应 1.5h， 生成 4-(2-Bromoethyl)-2,6-dimethoxyphenol
  参考文献：
  名称：

  Synthesis of raphanuside, an unusual oxathiane-fused thioglucoside isolated from the seeds of Raphanus sativus L.

  摘要：

  Raphanuside (1), an unusual oxathiane-fused thioglycoside isolated from the seeds of Raphanus sativus L., was synthesized via 10 steps and in 11% overall yield.[GRAPHICS](C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.11.020
• 作为产物：
  描述：

  对羟基苯乙醇 在 potassium peroxymonosulfate 、 碳酸二甲酯 、 sodium bromide 、 copper(I) bromide 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 生成 4-(2-hydroxyethyl)-2,6-dimethoxyphenol
  参考文献：
  名称：

  Synthesis and biological evaluation of gallic acid analogs

  摘要：

  A novel and efficient synthesis of pyrogallol moiety through a copper(I)-mediated C-O bond forming reaction is described. In particular, syntheses of 3,4,5-trihydroxyphenethyl alcohol and its methyl derivative are reported. Particular attention to dimethyl carbonate as an eco-friendly solvent/reactant has been paid, in order to improve the eco-compatibility of the whole synthetic pathway. Furthermore, the genotoxicity, cytotoxicity and the antioxidant activity of 3,4,5-trihydroxyphenethyl alcohol and its methyl derivative have been investigated.

  DOI：

  10.1007/s00044-012-0052-8

文献信息

• Novel c-Met inhibitory olive secoiridoid semisynthetic analogs for the control of invasive breast cancer
  作者：Mohamed M. Mohyeldin、Belnaser A. Busnena、Mohamed R. Akl、Ana Maria Dragoi、James A. Cardelli、Khalid A. El Sayed

  DOI：10.1016/j.ejmech.2016.04.043

  日期：2016.8

  reported tyrosol sinapate (4) as a c-Met inhibitor hit. This study reports additional semisynthetic optimization and SAR of 4 to improve its selective activity against c-Met-dependent breast cancer by increasing its capacity to inhibit c-Met phosphorylation. Forty-three compounds (5-47) were synthesized, among which the novel analog homovanillyl sinapate (HVS-16) was distinguished for its remarkable activity

  受体酪氨酸激酶c-Met失调及其配体HGF是治疗癌症的有效且有吸引力的分子靶标。受天然存在的橄榄类secrididoid（-）-oleocanthal（1）的化学结构的启发，并记录了其对c-Met依赖性恶性肿瘤的抗癌活性，以前的一项研究报道了酪氨酸溶胶鼻血酸盐（4）作为c-Met抑制剂的命中物。这项研究报告了额外的半合成优化和4的SAR，以通过增加其抑制c-Met磷酸化的能力来提高其对c-Met依赖性乳腺癌的选择性活性。合成了四十三种化合物（5-47），其中新颖的类似物高香草酸芥子酸酯（HVS-16）以其卓越的活性而著称。HVS-16大大削弱了c-Met介导的增殖，迁移，和在二维和三维培养系统中跨越人乳腺癌细胞系的侵袭，而发现相似的治疗剂量既不影响非致瘤性人乳腺上皮细胞的生长，也不影响c-Met独立乳腺癌细胞的生存能力。HVS-16在人乳腺癌细胞中显示出剂量依赖性抑制配体介导的c-Met活
• New convenient synthesis of iridol. An approach to the synthesis of ubiquinones
  作者：Paolo Bovicelli、Roberto Antonioletti、Maurizio Barontini、Giorgio Borioni、Roberta Bernini、Enrico Mincione

  DOI：10.1016/j.tetlet.2005.01.001

  日期：2005.2

  A strategy for the synthesis of ubiquinones, in which iridol is the key intermediate, has been developed, together with a new convenient synthesis of iridol (2,3-dimethoxy-5-methylphenol) starting from the easily available 4-methylphenol and using mild conditions and friendly and high-yielding reactions.

  已开发出一种以苯丙氨酸为主要中间体的泛醌合成策略，以及一种新的方便的合成方法，即从易于获得的4-甲基苯酚开始，并使用温和的方法，合成出一个新的方便的iridol（2,3-二甲氧基-5-甲基苯酚）合成方法。条件和友好而高产的反应。
• Profiling of the formation of lignin-derived monomers and dimers from <i>Eucalyptus</i> alkali lignin
  作者：Chengke Zhao、Zhenhua Hu、Lanlan Shi、Chen Wang、Fengxia Yue、Suxiang Li、Han Zhang、Fachuang Lu

  DOI：10.1039/d0gc01658f

  日期：——

  with the aid of evidence from authenticated compounds, a great treasure trove of lignin-derived phenolic compounds from Eucalyptus alkali lignin were disclosed. Except for some common monomeric products, as many as 15 new lignin-derived monomers and dimers including syringaglycerol, diarylmethane, 1,2-diarylethanes, 1,2-diarylethenes, (arylvinyl ether)-linked arylglycerol dimers and isomeric syringaresinols

  木质素是可再生的和最丰富的芳香来源，可用于广泛的化学品和材料。尽管每年制浆和造纸工业的副产品木质素产量约为5000万吨，但目前利用率不高。在考虑其应用时，了解技术木质素的结构特征非常重要。在这项工作中，我们证明了由硬木（桉树）形成低分子量成分木质素在化学制浆过程中比软木（云杉）木质素产生的低分子量成分要多得多，并通过二氯甲烷（DCM）萃取分离后分析了碱性木质素中的微分子组成。通过应用分析方法（凝胶渗透色谱法，2D NMR和GC-MS），在经过身份验证的化合物的证据的帮助下，桉树木质素衍生的酚类化合物大宝库公开了碱性木质素。除了一些常见的单体产品外，在产品中还鉴定出多达15种新的木质素衍生的单体和二聚体，包括丁香甘油酯，二芳基甲烷，1,2-二芳基乙烷，1,2-二芳基醚，（芳基乙烯基醚）连接的芳基甘油二聚体和异构体丁香油基醇。溶于DCM的馏分。关于Cα缩合的β-芳基醚结构的形成和演化，这是一种
• Simple and efficient synthesis of benzofuran derivatives from tyrosol
  作者：Paolo Bovicelli、Fabrizio Bottaro、Carla Sappino、Michela Tomei、Valentina Nardi、Ilaria Proietti Silvestri、Beatrice Macchi、Caterina Frezza、Giuliana Righi

  DOI：10.1080/00397911.2015.1133828

  日期：2016.2

  A convenient strategy for the preparation of compounds bearing the benzofuran skeleton starting from tyrosol, a phenol largely present in olive oil production waste, with no biological importance, is reported. A bromination/methoxylation sequence, already described for the synthetic transformation of naturally occurring compounds, was exploited. Depending on the solvent used for the methoxylation reaction together with the presence of a 4-phenol moiety respect to the side chain, benzodihydrofurans or a benzofurans derivative can be obtained.
• Arlt et al., Tappi, 1958, vol. 41, p. 64,65
  作者：Arlt et al.

  DOI：——

  日期：——