2-(3-methylbutyl)-1,3,5-trimethoxybenzene | 219954-49-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(3-methylbutyl)-1,3,5-trimethoxybenzene
• 英文别名: 1-(3-methylbutyl)-2,4,6-trimethoxybenzene；1,3,5-Trimethoxy-2-(3-methylbutyl)benzene
• CAS: 219954-49-1
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: WJZGWKJGTOPNFK-UHFFFAOYSA-N

物化性质

• 沸点：
  320.6±37.0 °C(Predicted)
• 密度：
  0.976±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-methylbutyl)-1,3,5-trimethoxybenzene 在 溴 、 叔丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 Dimethyl 2,4,6-trimethoxy-5-(3-methylbutyl)benzene-1,3-dicarboxylate
  参考文献：
  名称：

  从巨桉中分离的新型间苯三酚衍生物Grandinal的首次全合成

  摘要：

  Grandinal (1) 的第一次全合成是通过 jensenone 衍生物 (2) 和由 Grandinol (4) 氧化产生的邻醌甲基化物 (3) 的仿生环加成反应完成的。

  DOI：

  10.1246/cl.2001.210
• 作为产物：
  描述：

  异戊酰氯 在 Adam’s catalyst lithium aluminium tetrahydride 、 三氯化铝 、 氢气 作用下， 以 氯仿 为溶剂， 反应 20.5h， 生成 2-(3-methylbutyl)-1,3,5-trimethoxybenzene
  参考文献：
  名称：

  从巨桉中分离的新型间苯三酚衍生物Grandinal的首次全合成

  摘要：

  Grandinal (1) 的第一次全合成是通过 jensenone 衍生物 (2) 和由 Grandinol (4) 氧化产生的邻醌甲基化物 (3) 的仿生环加成反应完成的。

  DOI：

  10.1246/cl.2001.210

文献信息

• Hydrosilanes are not always a reducing reagent: a ruthenium-catalyzed introduction of primary alkyl groups to electron-rich aromatic rings using esters as a source of the alkyl groups
  作者：Hideo Nagashima、Yuichi Kubo、Mitsunobu Kawamura、Takashi Nishikata、Yukihiro Motoyama

  DOI：10.1016/j.tet.2011.08.033

  日期：2011.10

  reaction of electron-rich aromatic rings using a combination of hydrosilane and ester as a source of the primary-alkyl group. The reaction involves electrophilic substitution of arenes by carbocationic species stabilized by a neighboring alkoxy or siloxy group generated during the reduction of esters giving alkylated arenes after reductive removal of the alkoxy or siloxy group at the benzylic position

  甲羰基三钌簇，（μ 3，η 2，η 3，η 5 -acenaphthylene）的Ru 3（CO）7有效地催化氢硅烷使用和酯的组合作为主要的来源的富电子的芳族环的主烷基化反应-烷基。该反应涉及芳烃的电取代，该芳烃被在还原除去苄基位置上的烷氧基或甲硅烷氧基的酯的还原过程中产生的相邻烷氧基或甲硅烷氧基所稳定的碳阳离子物质所取代。
• Production of hop extracts having oestrogenic and antiproliferative bioactivity
  申请人：Biodynamics

  公开号：EP1543834A1

  公开（公告）日：2005-06-22

  The invention relates to a method for the production of a hop extract enriched in prenylated flavonoids or derivatives thereof, whereby the method comprises the steps of subjecting a hop product to an isomerisation reaction in the presence of an amount of a base and to at least one extraction.

  这项发明涉及一种生产富含前缀化黄酮类化合物或其衍生物的啤酒花提取物的方法，其中该方法包括以下步骤：在碱的存在下对啤酒花产品进行异构化反应，并至少进行一次提取。
• Subtle Side-Chain Modifications of the Hop Phytoestrogen 8-Prenylnaringenin Result in Distinct Agonist/Antagonist Activity Profiles for Estrogen Receptors α and β
  作者：Frederik Roelens、Nina Heldring、Willem Dhooge、Martin Bengtsson、Frank Comhaire、Jan-Åke Gustafsson、Eckardt Treuter、Denis De Keukeleire

  DOI：10.1021/jm060692n

  日期：2006.12.1

  In search of therapeutic agents for estrogen-related pathologies, phytoestrogens are being extensively explored. In contrast to naringenin, 8-prenylnaringenin is a potent hop-derived estrogenic compound, highlighting the importance of the prenyl group for hormonal activity. We investigated the effects of substituting the prenyl group at C(8) with alkyl chains of varying lengths and branching patterns on estrogen receptor (ER) subtype ER alpha- and ER beta-binding affinities and transcriptional activities. In addition, features of the ligand-induced receptor conformations were explored using a set of specific ER-binding peptides. The new 8-alkylnaringenins were found to span an activity spectrum ranging from full agonism to partial agonism to antagonism. Most strikingly, 8-(2,2-dimethylpropyl) naringenin exhibited full agonist character on ERR, but pronounced antagonist character on ER beta. Knowledge on how ER-subtype-selective activities can be designed provides valuable information for future drug or tool compound discovery.
• PRODUCTION OF HOP EXTRACTS HAVING OESTROGENIC AND ANTIPROLIFERATIVE BIOACTIVITY
  申请人：Biodynamics

  公开号：EP1727555A1

  公开（公告）日：2006-12-06
• Method for the production of enriched hop extracts having combined oestrogenic and antiproliferative bioactivity
  申请人：Maes Francis

  公开号：US20070110835A1

  公开（公告）日：2007-05-17

  The present invention relates to a method for the production of a hop extract which is enriched in 8-prenylnaringenin with respect to 6-prenylnaringenin, which method comprises the steps of subjecting a hop product to (1) an isomerisation reaction in the presence of water as a solvent and in the presence of an amount of a base and (2) to at least one extraction. In that way a hop extract may be extract is obtained which contains 6-prenylnaringenin and 8-prenylinaringening in a ratio (8-prenylnaringenin ×100%)/(8-prenylnaringenin+6-prenylnaringenin) of at least 50%. The extract preferably also contains xanthohumol, the weight ratio of xanthohumol to 8-prenylnaringenin being at least 10.