2-(2,2-dimethylpropyl)-3,5-dimethoxyphenol | 870681-71-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(2,2-dimethylpropyl)-3,5-dimethoxyphenol
• CAS: 870681-71-3
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: UTUMCWYESMPPAC-UHFFFAOYSA-N

物化性质

• 沸点：
  336.3±37.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：

  2-(2,2-dimethylpropyl)-3,5-dimethoxyphenol 在 三氟化硼乙醚 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 生成 8-(2,2-Dimethyl-propyl)-5,7-dihydroxy-4-(4-hydroxy-phenyl)-chroman-2-one
  参考文献：
  名称：

  Regioselective synthesis and estrogenicity of (±)-8-alkyl-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydrocoumarins

  摘要：

  Nine new (+/-)-8-alkyl-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydrocoumarins have been synthesized from 2,4,6-trimethoxybenzaldehyde via a short, efficient, and regioselective pathway, together with the unsubstituted analogue (+/-)-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydrocoumarin. The compounds were tested for estrogenic activity using a yeast-based estrogen screen. Weak estrogenicity was determined for seven members of the series. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.04.010
• 作为产物：
  描述：

  2,4,6-三甲氧基苯甲醛 在 三乙基硅烷 、 三溴化硼 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-(2,2-dimethylpropyl)-3,5-dimethoxyphenol
  参考文献：
  名称：

  Regioselective synthesis and estrogenicity of (±)-8-alkyl-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydrocoumarins

  摘要：

  Nine new (+/-)-8-alkyl-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydrocoumarins have been synthesized from 2,4,6-trimethoxybenzaldehyde via a short, efficient, and regioselective pathway, together with the unsubstituted analogue (+/-)-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydrocoumarin. The compounds were tested for estrogenic activity using a yeast-based estrogen screen. Weak estrogenicity was determined for seven members of the series. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.04.010

文献信息

• [EN] INTRODUCTION OF ALKYL SUBSTITUENTS TO AROMATIC COMPOUNDS<br/>[FR] INTRODUCTION DE SUBSTITUANTS ALKYLE DANS DES COMPOSÉS AROMATIQUES
  申请人：B G NEGEV TECH AND APPLICATIONS LTD AT BEN-GURION UNIV

  公开号：WO2016132355A1

  公开（公告）日：2016-08-25

  Novel selective synthesis route to introduce primary alkyl groups on aromatic compounds is disclosed. The synthesis route is based on electrophilic aromatic substitutions of thionium ion species that are generated in-situ from aldehydes and thiols, affording benzyl sulfide that can be reduced with triethylsilane.

  披露了一种新颖的选择性合成路线，用于在芳香化合物上引入初级烷基团。该合成路线基于在芳香取代反应中生成的硫正离子物种，这些硫正离子物种是从醛和硫醇原位生成的，从而得到可以与三乙基硅烷还原的苯甲基硫醚。
• Introduction of alkyl substituents to aromatic compounds
  申请人：B. G. NEGEV TECHNOLOGIES AND APPLICATIONS LTD., AT BEN-GURION UNIVERSITY

  公开号：US10351492B2

  公开（公告）日：2019-07-16

  Novel selective synthesis route to introduce primary alkyl groups on aromatic compounds is disclosed. The synthesis route is based on electrophilic aromatic substitutions of thionium ion species that are generated in-situ from aldehydes and thiols, affording benzyl sulfide that can be reduced with triethylsilane.

  本发明公开了在芳香族化合物上引入伯烷基的新型选择性合成路线。该合成路线基于由醛和硫醇原位生成的硫离子物种的亲电芳香取代，从而得到可被三乙基硅烷还原的苄基硫醚。
• Reductive Alkylation of Arenes by a Thiol-Based Multicomponent Reaction
  作者：Regev Parnes、Doron Pappo

  DOI：10.1021/acs.orglett.5b01142

  日期：2015.6.19

  A simple and highly chemo- and regioselective method for introducing primary alkyl substituents into aromatic compounds was developed. The method is based on an electrophilic aromatic substitution of an aldehyde, promoted by a thiol, to afford 1-(alkylthio)alkylarenes, which can either be reduced in situ with triethylsilane or reacted further. This multicomponent reaction enables the direct introduction of both aromatic and linear and branched aliphatic alkyl groups into arenes. The above one-pot protocol may be performed in air and in the presence of water and is compatible with various functional groups.
• INTRODUCTION OF ALKYL SUBSTITUENTS TO AROMATIC COMPOUNDS
  申请人：B.G. NEGEV TECHNOLOGIES AND APPLICATIONS LTD., AT BEN-GURION UNIVERSITY

  公开号：US20180065904A1

  公开（公告）日：2018-03-08

  Novel selective synthesis route to introduce primary alkyl groups on aromatic compounds is disclosed. The synthesis route is based on electrophilic aromatic substitutions of thionium ion species that are generated in-situ from aldehydes and thiols, affording benzyl sulfide that can be reduced with triethylsilane.
• Regioselective synthesis and estrogenicity of (±)-8-alkyl-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydrocoumarins
  作者：Frederik Roelens、Kevin Huvaere、Willem Dhooge、Marjan Van Cleemput、Frank Comhaire、Denis De Keukeleire

  DOI：10.1016/j.ejmech.2005.04.010

  日期：2005.10

  Nine new (+/-)-8-alkyl-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydrocoumarins have been synthesized from 2,4,6-trimethoxybenzaldehyde via a short, efficient, and regioselective pathway, together with the unsubstituted analogue (+/-)-5,7-dihydroxy-4-(4-hydroxyphenyl)-3,4-dihydrocoumarin. The compounds were tested for estrogenic activity using a yeast-based estrogen screen. Weak estrogenicity was determined for seven members of the series. (c) 2005 Elsevier SAS. All rights reserved.