[3-Methoxy-5-(methoxymethoxy)phenyl]methanol | 126809-66-3

• 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: [3-Methoxy-5-(methoxymethoxy)phenyl]methanol
• CAS: 126809-66-3
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: HKHVEQHXMDJLCC-UHFFFAOYSA-N

物化性质

• 沸点：
  339.0±37.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [3-Methoxy-5-(methoxymethoxy)phenyl]methanol 在 咪唑 、 正丁基锂 、 四丁基氟化铵 、 copper(I) bromide 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-(4-(3,7-dimethylocta-2,6-dien-1-yl)-3-methoxy-5-(methoxymethoxy)phenyl)methanol
  参考文献：
  名称：

  Relevance of the C-5 position to schweinfurthin induced cytotoxicity

  摘要：

  The schweinfurthins are an intriguing group of anti-proliferative agents that display low nanomolar activities against several cell types, including the human-derived glioblastoma cell line SF-295, but have little impact on other cell lines even at micromolar concentrations. This activity has inspired the synthesis of seven of the natural schweinfurthins, all with the correct absolute stereochemistry, and a variety of analogues designed to probe different facets of the pharmacophore. Reported herein is the synthesis of several new schweinfurthin analogues varied at the C-5 position along with data on their biological activity in the NCI 60 cell-line assay. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.034
• 作为产物：
  描述：

  3-羟基-5-甲氧基苯甲醛 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 [3-Methoxy-5-(methoxymethoxy)phenyl]methanol
  参考文献：
  名称：

  13C NMR chemical shifts of the carbon atoms of the methoxymethyl group of di-ortho-substituted aromatic methoxymethyl ethers

  摘要：

  完成了28种具有不同取代基和取代模式的芳香甲氧甲基醚的完整13C谱归属。在间位、对位或单一邻位取代的情况下，甲氧甲基碳原子的13C共振并未显著受到影响，但邻位双取代导致了两个碳原子的去屏蔽效应，其中甲叉基碳原子上的这一效应更为明显。

  DOI：

  10.1002/mrc.1260271213

文献信息

• [EN] SCHWEINFURTHIN ANALOGUES<br/>[FR] ANALOGUES DE LA SCHWEINFURTHINE
  申请人：UNIV IOWA RES FOUND

  公开号：WO2009158516A1

  公开（公告）日：2009-12-30

  The invention provides fluorescent schweinfurthin analogs of formula(I) which are useful as probes and for the treatment of cancer and other diseases.

  该发明提供了公式(I)的荧光施文富尔汀类似物，可用作探针，用于治疗癌症和其他疾病。
• Total synthesis of (R,R,R)- and (S,S,S)-schweinfurthin F: Differences of bioactivity in the enantiomeric series
  作者：Nolan R. Mente、Andrew J. Wiemer、Jeffrey D. Neighbors、John A. Beutler、Raymond J. Hohl、David F. Wiemer

  DOI：10.1016/j.bmcl.2006.11.096

  日期：2007.2

  Total synthesis of the (R,R,R)- and (S,S,S)-enantiomers of the natural product schweinfurthin F has been completed. Comparisons of spectral data and optical rotations with those reported for the natural product, as well as a variety of bioassay data, allow assignment of the natural material as the (R,R,R)-isomer.

  天然产物schweinfurthin F的（R，R，R）-和（S，S，S）-对映异构体的全合成已完成。光谱数据和旋光度与天然产物的光谱数据和旋光度的比较以及各种生物测定数据的比较，可以将天然物质指定为（R，R，R）异构体。
• Fluorescent schweinfurthin B and F analogs with anti-proliferative activity
  作者：Joseph J. Topczewski、Craig H. Kuder、Jeffrey D. Neighbors、Raymond J. Hohl、David F. Wiemer

  DOI：10.1016/j.bmc.2010.07.056

  日期：2010.9

  The natural tetracyclic schweinfurthins are potent and selective inhibitors of cell growth in the National Cancer Institute's 60 cell-line screen. At this time, the mechanism or cellular target that underlies this activity has not yet been identified, and efforts to illuminate the schweinfurthins' mode of action would benefit from development of potent fluorescent analogs that could be readily visualized within cells. This report describes the synthesis of fluorescent analogs of schweinfurthins B and F, and demonstrates that these compounds retain the potent and differentially toxic activities against select human cancer cells that are characteristic of the natural schweinfurthins. In addition, the synthesis of control compounds that maintain parallel fluorescent properties, but lack the potent activity of the natural schweinfurthin is described. Use of fluorescence microscopy shows differences between the localization of the active and relatively inactive schweinfurthin analogs. The active compounds localize in peripheral puncta which may identify the site(s) of activity. (c) 2010 Elsevier Ltd. All rights reserved.
• Biologically active biotin derivatives of schweinfurthin F
  作者：Natalie C. Ulrich、Craig H. Kuder、Raymond J. Hohl、David F. Wiemer

  DOI：10.1016/j.bmcl.2010.08.143

  日期：2010.11

  As a prelude to efforts to identify schweinfurthin binding proteins, an ester conjugate and an amide conjugate of schweinfurthin F and biotin have been prepared by chemical synthesis. These compounds maintain activity in SF-295 cells comparable to the parent system, and display the lower potency in A549 cells that is a characteristic of the schweinfurthin pattern of activity. (C) 2010 Elsevier Ltd. All rights reserved.