1-(3,4-dimethoxyphenyl)-2,2-dimethylpropan-1-ol | 213267-13-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3,4-dimethoxyphenyl)-2,2-dimethylpropan-1-ol
• 英文别名: 1-(3,4-Dimethoxyphenyl)-2,2-dimeth-ylpropan-1-ol
• CAS: 213267-13-1
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: PRYGIAUZBXMTAD-UHFFFAOYSA-N

物化性质

• 沸点：
  320.1±37.0 °C(Predicted)
• 密度：
  1.028±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(3,4-dimethoxyphenyl)-2,2-dimethylpropan-1-ol 在 laccase 、 N-羟基邻苯二甲酰亚胺 、 氧气 作用下， 以 various solvent(s) 为溶剂， 反应 24.0h， 以70%的产率得到1-(3,4-二甲氧基苯基)-2,2-二甲基丙烷-1-酮
  参考文献：
  名称：

  Promoting laccase activity towards non-phenolic substrates: a mechanistic investigation with some laccase–mediator systems

  摘要：

  在适当的介体化合物中介下，酶漆酶对苄醇的氧化反应产生羰基产物，而漆酶无法直接氧化这些非酚类底物。氧化步骤是通过介体（Medox）的氧化形式进行的，该形式在介体与漆酶相互作用后生成。Medox可通过电子转移（ET）或自由基氢原子转移（HAT）途径进行底物氧化。报告了实验证据，能够明确评估每个研究介体（ABTS、HBT、HPI和VLA）发生哪种氧化途径。以下提供了对结论的支持：（i）研究适当的底物氧化间的分子选择性，（ii）尝试对一系列4-X取代苄醇氧化进行Hammett相关性分析，（iii）测量动力学同位素效应，（iv）研究适当的探针前体的产品模式。基于这些点，漆酶-HBT、漆酶-HPI和漆酶-VLA系统遵循HAT机制，而漆酶-ABTS系统中ET途径似乎可行。

  DOI：

  10.1039/b208951c
• 作为产物：
  描述：

  1-(3,4-二甲氧基苯基)-2,2-二甲基丙烷-1-酮 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 1-(3,4-dimethoxyphenyl)-2,2-dimethylpropan-1-ol
  参考文献：
  名称：

  合成3,3,4-三甲基-3,4-二氢异喹啉衍生物的Retropinacol重排

  摘要：

  Veratrole与新戊醛和腈（氰基乙酸乙酯，氰基乙酰胺和苄腈）在浓硫酸中的三组分缩合导致形成1-取代的6,7-二甲氧基-3,3,4-三甲基-3,4-二氢异喹啉。

  DOI：

  10.1134/s107042800912015x

文献信息

• Brønsted Acid Catalyzed Tandem Defunctionalization of Biorenewable Ferulic acid and Derivates into Bio‐Catechol
  作者：Jeroen Bomon、Elias Van Den Broeck、Mathias Bal、Yuhe Liao、Sergey Sergeyev、Veronique Van Speybroeck、Bert F. Sels、Bert U. W. Maes

  DOI：10.1002/anie.201913023

  日期：2020.2.17

  H2 SO4 ) as catalyst in pressurized hot water (250 °C, 50 bar N2 ). The versatility is shown on a variety of other (biorenewable) substrates yielding up to 84 % di- (catechol, resorcinol, hydroquinone) and trihydroxybenzenes (pyrogallol, hydroxyquinol), in most cases just requiring simple extraction as work-up.

  已经开发了将可生物更新的阿魏酸有效转化为生物邻苯二酚的方法。该转化包括在一个步骤中发生的两个连续的底物去官能化，即CO（去甲基化）和CC（去2-羧基乙烯基化）键裂解。该过程仅需要在加压热水（250°C，50 bar N2）中将阿魏酸与HCl（或H2 SO4）作为催化剂加热。在多种其他（生物可再生）底物上也显示出多功能性，可产生高达84％的二-（邻苯二酚，间苯二酚，对苯二酚）和三羟基苯（邻苯三酚，羟基喹啉），在大多数情况下，仅需简单提取即可进行后处理。
• Aerobic Oxidation of Benzyl Alcohols Catalyzed by Aryl Substituted <i>N-</i>Hydroxyphthalimides. Possible Involvement of a Charge-Transfer Complex
  作者：Claudia Annunziatini、Maria Francesca Gerini、Osvaldo Lanzalunga、Marco Lucarini

  DOI：10.1021/jo049887y

  日期：2004.5.1

  exclusive products in the oxidation of secondary alcohols. O−H bond dissociation enthalpies (BDEs) of X-NHPIs have been determined by using the EPR radical equilibration technique. BDEs increase with increasing the electron-withdrawing properties of the aryl substituent. Kinetic isotope effect studies and the increase of the substrate oxidation rate by increasing the electron-withdrawing power of the NHPI

  一系列含有吸电子基团（4-CH 3 OCO，3-F）或给电子基团（4-CH 3，4 -CH 3 O，3-的芳基取代的N-羟基邻苯二甲酰亚胺（X-NHPI）CH 3 O，3,6-（CH 3 O）2）已被用作伯苄醇和仲苄醇的有氧氧化的催化剂。在伯醇的氧化中观察到芳香醛的选择性形成。芳族酮是仲醇氧化的唯一产物。X-NHPI的O-H键离解焓（BDE）已使用EPR自由基平衡技术确定。BDEs随着芳基取代基吸电子性能的提高而增加。动力学同位素效应研究以及通过增加NHPI芳基取代基的吸电子能力来提高底物氧化速率表明，速率决定了从醇到芳基取代的邻苯二甲酰亚胺-N的苄基氢原子转移（HAT）-氧基自由基（X-PINO）。除焓效应外，极性效应还在HAT过程中起作用，如Hammett相关系数与σ +的负ρ值以及通过增加电子-而使ρ值减小（从-0.54到-0.70）所表明的。 NHPI芳基取代基的吸水性。3-CH 3
• TRPM8 receptor agonist compounds and uses thereof
  申请人：UNIVERSIDAD MIGUEL HERNANDEZ DE ELCHE

  公开号：US10905679B2

  公开（公告）日：2021-02-02

  The invention relates to compounds having formula (I) wherein A is selected from the group consisting of: a) optionally substituted (C1-C8) alkyl; b) optionally substituted (C3-C6) cycloalkyl; c) optionally substituted (C6-C14) aryl; d) optionally substituted (C6-C14) heteroaryl; e) C(O)—(C6-C14) aryl, in which group (C6-C14) aryl is optionally substituted; f) C(O)—(C6-C14) heteroaryl, in which group (C6-C14) heteroaryl is optionally substituted; g) CH(OH)—(C6-C14) aryl, in which group (C6-C14) aryl is optionally substituted; and h) CH(OH)—(C6-C14) heteroaryl, in which group (C6-C14) heteroaryl is optionally substituted. The invention also relates to methods for the production of said compounds, to pharmaceutical and veterinary compositions comprising said compounds and to the therapeutic uses thereof, such as for the prevention and/or treatment of dry eye syndrome, vaginal dryness and/or burning mouth syndrome.

  本发明涉及具有式 (I) 的化合物，其中 A 选自以下组成的组：a) 任选取代的(C1-C8)烷基； b) 任选取代的(C3-C6)环烷基； c) 任选取代的(C6-C14)芳基； d) 任选取代的(C6-C14)杂芳基； e) C(O)-(C6-C14)芳基，其中基团(C6-C14)芳基被任选取代；f) C(O)-(C6-C14)杂芳基，其中基团(C6-C14)杂芳基被任选取代； g) CH(OH)-(C6-C14)芳基，其中基团(C6-C14)芳基被任选取代；以及 h) CH(OH)-(C6-C14)杂芳基，其中基团(C6-C14)杂芳基被任选取代。本发明还涉及生产所述化合物的方法、包含所述化合物的药物和兽药组合物及其治疗用途，例如用于预防和/或治疗干眼症、阴道干燥症和/或灼口症。
• Lifetime, Reduction Potential and Base-Induced Fragmentation of the Veratryl Alcohol Radical Cation in Aqueous Solution. Pulse Radiolysis Studies on a Ligninase “Mediator”
  作者：Massimo Bietti、Enrico Baciocchi、Steen Steenken

  DOI：10.1021/jp9812482

  日期：1998.9.1

  The radical cation of veratryl alcohol (3,4-dimethoxybenzyl alcohol), VA(.+), was produced in aqueous solution, mainly by oxidation with the radiation chemically generated SO4.- or Tl2+. By electron-transfer equilibration with thioanisole as a redox standard, the reduction potential of VA(.+) was determined to be 1.36 +/- 0.01 V/NHE. On the basis of product analysis results, the radical cation undergoes a C-H deprotonation reaction from the side chain, leading to an alpha-hydroxybenzyl-type radical, with k = (17 +/- 1) s(-1) at pH less than or equal to 5, as determined by time-resolved conductance. The alpha-hydroxybenzyl-type radical was also produced by reduction of veratryl aldehyde with the hydrated electron, and the pK(a) value of this radical was determined to be 10.0. The deprotonation of VA(.+) is enhanced by bases such as OH-, with the rate constant being 1.3 x 10(9) M-1 s(-1) In contrast, the corresponding rate constant for reaction of OH- with the radical cation of veratryl alcohol methyl ether; whose reduction potential is also 1.36 V/NHE, is only 2 x 10(7) M-1 s(-1) With the veratryl alcohol derivative, 3,4-(MeO)(2)C6H3CH(OH)CMe3, the radical cation undergoes both a proton loss from the benzylic position and a C-alpha-C-beta fragmentation with the ratio, at pH less than or equal to 5, of ca. 1:2. The decay of the radical cation is strongly enhanced by OH- (k = 8.3 x 10(9) M-1 s(-1)), with the base induction favoring the C-C fragmentation relative to the proton loss from the benzylic position. The possible bearing of these results with respect to the role of VA in the lignin peroxidase-catalyzed decomposition of lignin is discussed.
• TRPM8 RECEPTOR AGONIST COMPOUNDS AND USES THEREOF
  申请人：UNIVERSIDAD MIGUEL HERNANDEZ DE ELCHE

  公开号：US20190022068A1

  公开（公告）日：2019-01-24

  The invention relates to compounds having formula (I) wherein A is selected from the group consisting of: a) optionally substituted (C 1 -C 8 ) alkyl; b) optionally substituted (C 3 -C 6 ) cycloalkyl; c) optionally substituted (C 6 -C 14 ) aryl; d) optionally substituted (C 6 -C 14 ) heteroaryl; e) C(O)—(C 6 -C 14 ) aryl, in which group (C 6 -C 14 ) aryl is optionally substituted; f) C(O)—(C 6 -C 14 ) heteroaryl, in which group (C 6 -C 14 ) heteroaryl is optionally substituted; g) CH(OH)—(C 6 -C 14 ) aryl, in which group (C 6 -C 14 ) aryl is optionally substituted; and h) CH(OH)—(C 6 -C 14 ) heteroaryl, in which group (C 6 -C 14 ) heteroaryl is optionally substituted. The invention also relates to methods for the production of said compounds, to pharmaceutical and veterinary compositions comprising said compounds and to the therapeutic uses thereof, such as for the prevention and/or treatment of dry eye syndrome, vaginal dryness and/or burning mouth syndrome.