(3,4-bis(methoxymethoxy)-2-(3-methylbut-2-en-1-yl)phenyl)methanol | 1075694-36-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3,4-bis(methoxymethoxy)-2-(3-methylbut-2-en-1-yl)phenyl)methanol
• 英文别名: [3,4-bis(methoxymethoxy)-2-(3-methylbut-2-enyl)phenyl]methanol；[3,4-Bis(methoxymethoxy)-2-(3-methylbut-2-enyl)phenyl]methanol
• CAS: 1075694-36-8
• 化学式: C₁₆H₂₄O₅
• 分子量: 296.364
• InChiKey: GAEMNACAPLZMOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3,4-bis(methoxymethoxy)-2-(3-methylbut-2-en-1-yl)phenyl)methanol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以79%的产率得到3,4-bis(methoxymethoxy)-2-(3-methylbut-2-enyl)benzaldehyde
  参考文献：
  名称：

  A Concise Synthesis of Pawhuskin A

  摘要：

  Pawhuskin A is an isoprenylated stilbene that was isolated from Dalea purpurea and reported to have affinity for the opioid receptor in vitro. It has been synthesized through a convergent sequence that joins a prenylated aldehyde with a geranylated phosphonate in a stereoselective Horner-Wadsworth-Emmons condensation to afford the target E olefin isomer. This synthesis confirms the structure assigned to the natural product and establishes a route that may be used to explore its biological activity and to prepare more active analogues.

  DOI：

  10.1021/np800351c
• 作为产物：
  描述：

  2-bromo-3,4-dihydroxybenzaldehyde 在 咪唑 、 sodium tetrahydroborate 、 正丁基锂 、 四丁基氟化铵 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 13.23h， 生成 (3,4-bis(methoxymethoxy)-2-(3-methylbut-2-en-1-yl)phenyl)methanol
  参考文献：
  名称：

  保护性酚的选择性烯丙基化反应，用于合成Pawhuskin A类似物

  摘要：

  Pawhuskin A是一种异戊二烯基二苯乙烯，起着κ阿片受体拮抗剂的作用。这种天然产物在A环上带有异戊二烯基的不同位置的类似物已显示出对κ或δ受体亚型的选择性。这种差异活性已经引起人们对C-2，C-5和C-6戊烯基化A环区域异构体的区域特异性制备的关注。通过卤素金属交换，已制备出代表这些区域异构体中每一种的高级中间体，并且新的C-6中间体已转化为天然二苯乙烯的新类似物。

  DOI：

  10.1021/acs.joc.5b02756

文献信息

• THERAPEUTIC COMPOUNDS AND METHODS
  申请人：UNIVERSITY OF IOWA RESEARCH FOUNDATION

  公开号：US20170107173A1

  公开（公告）日：2017-04-20

  Compounds of formula I: and salts thereof are disclosed. Also disclosed are pharmaceutical compositions comprising a compound of formula I, processes for preparing compounds of formula I, intermediates useful for preparing compounds of formula I and therapeutic methods for treating various diseases and conditions.

  公开了化学式I的化合物及其盐。还公开了包括化学式I的化合物的药物组合物，制备化学式I的化合物的方法，制备化学式I的化合物有用的中间体以及治疗各种疾病和病况的治疗方法。
• A selective delta opioid receptor antagonist based on a stilbene core
  作者：Alyssa M. Hartung、Hernan A. Navarro、David F. Wiemer、Jeffrey D. Neighbors

  DOI：10.1016/j.bmcl.2015.10.059

  日期：2015.12

  Studies of directed ortho metalation reactions on an aromatic substrate with multiple potential directing groups have identified conditions that favor either of two regioisomers. One of these regioisomers has been converted to an analogue of the stilbene pawhuskin A, and been shown to have high selectivity as an antagonist of the delta opioid receptor. Docking studies have suggested that this compound can adopt a conformation similar to naltrindole, a known delta antagonist. (C) 2015 Elsevier Ltd. All rights reserved.
• Selective Prenylation of Protected Phenols for Synthesis of Pawhuskin A Analogues
  作者：Kevyn D. Gardner、David F. Wiemer

  DOI：10.1021/acs.joc.5b02756

  日期：2016.2.19

  is a prenylated stilbene that functions as an antagonist of the kappa opioid receptor. Analogues of this natural product bearing different placements of the prenyl group in the A-ring have shown selectivity for either the kappa or the delta receptors subtypes. This differential activity has drawn attention to regiospecific preparation of the C-2, C-5, and C-6 prenylated A-ring regioisomers. Through

  Pawhuskin A是一种异戊二烯基二苯乙烯，起着κ阿片受体拮抗剂的作用。这种天然产物在A环上带有异戊二烯基的不同位置的类似物已显示出对κ或δ受体亚型的选择性。这种差异活性已经引起人们对C-2，C-5和C-6戊烯基化A环区域异构体的区域特异性制备的关注。通过卤素金属交换，已制备出代表这些区域异构体中每一种的高级中间体，并且新的C-6中间体已转化为天然二苯乙烯的新类似物。
• A Concise Synthesis of Pawhuskin A
  作者：Jeffrey D. Neighbors、Matthew J. Buller、Kelly D. Boss、David F. Wiemer

  DOI：10.1021/np800351c

  日期：2008.12.1

  Pawhuskin A is an isoprenylated stilbene that was isolated from Dalea purpurea and reported to have affinity for the opioid receptor in vitro. It has been synthesized through a convergent sequence that joins a prenylated aldehyde with a geranylated phosphonate in a stereoselective Horner-Wadsworth-Emmons condensation to afford the target E olefin isomer. This synthesis confirms the structure assigned to the natural product and establishes a route that may be used to explore its biological activity and to prepare more active analogues.