4-hydroxybenzyl 2-(2-methoxyethoxy)ethyl ether | 115319-74-9

• 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: 4-hydroxybenzyl 2-(2-methoxyethoxy)ethyl ether
• 英文别名: 4-{2-(2-methoxyethoxy)ethoxymethyl}phenol；4-[2-(2-Methoxyethoxy)ethoxymethyl]phenol
• CAS: 115319-74-9
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: XZJLXAKHLDUALC-UHFFFAOYSA-N

物化性质

• 沸点：
  337.2±27.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  4-hydroxybenzyl 2-(2-methoxyethoxy)ethyl ether 在 iron(III) chloride 作用下， 以97%的产率得到二乙二醇单甲醚
  参考文献：
  名称：

  Compounds and methods of arylmethylation (benzylation) as protection for alcohol groups during chemical synthesis

  摘要：

  一种对醇进行苄基化的过程包括将2-苄氧基-1-甲基吡啶三氟甲磺酸盐与具有预定沸点的芳香烃溶剂混合；向混合物中加入酸中和剂；将待苄基化的醇与混合物结合；通过加热至高于环境温度使醇与2-苄氧基-1-甲基吡啶三氟甲磺酸盐发生反应以生成苄基化醇；并将苄基化醇与混合物分离。

  公开号：

  US07754909B1
• 作为产物：
  描述：

  在 四丁基氟化铵 、 三甲基乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以99%的产率得到4-hydroxybenzyl 2-(2-methoxyethoxy)ethyl ether
  参考文献：
  名称：

  Compounds and methods of arylmethylation (benzylation) as protection for alcohol groups during chemical synthesis

  摘要：

  一种对醇进行苄基化的过程包括将2-苄氧基-1-甲基吡啶三氟甲磺酸盐与具有预定沸点的芳香烃溶剂混合；向混合物中加入酸中和剂；将待苄基化的醇与混合物结合；通过加热至高于环境温度使醇与2-苄氧基-1-甲基吡啶三氟甲磺酸盐发生反应以生成苄基化醇；并将苄基化醇与混合物分离。

  公开号：

  US07754909B1

文献信息

• Cell adhesion-inhibiting antiinflammatory compounds
  申请人：Abbott Laboratories

  公开号：US06232320B1

  公开（公告）日：2001-05-15

  Compounds having Formula I are useful for treating inflammation. Also disclosed are pharmaceutical compositions comprising compounds of Formula I, and methods of inhibiting/treating inflammatory diseases in a mammal.

  具有I式化学式的化合物对于治疗炎症是有用的。还公开了包含I式化合物的药物组合物，以及在哺乳动物中抑制/治疗炎症性疾病的方法。
• On the metalation of phenolic compounds: Ready access to highly substituted phenols.
  作者：Antonio Costa、José M. Saá

  DOI：10.1016/s0040-4039(00)96778-9

  日期：1987.1

  studied. Those substrates possesing an electron-withdrawing group in a 1,3 relationship with the coordinating (-CH2OMe) group underwent regioselective metalation by the action of n-BuLi/THF. Highly substituted phenols can thus be readly prepared.

  已经研究了几种对羟基苄基甲基醚的直接金属化。那些具有与配位基团（-CH 2 OMe）成1,3关系的吸电子基团的底物在n-BuLi / THF的作用下进行了区域选择性金属化。因此可以容易地制备高度取代的酚。
• Selective Inhibition of ICAM-1 and E-Selectin Expression in Human Endothelial Cells. 2. Aryl Modifications of 4-(Aryloxy)thieno[2,3-<i>c</i>]pyridines with Fine-Tuning at C-2 Carbamides
  作者：Gui-Dong Zhu、David L. Arendsen、Indrani W. Gunawardana、Steven A. Boyd、Andrew O. Stewart、Dennis G. Fry、Barbara L. Cool、Lemma Kifle、Verlyn Schaefer、Joseph Meuth、Kennan C. Marsh、Anita J. Kempf-Grote、Patrick Kilgannon、W. Michael Gallatin、Gregory F. Okasinski

  DOI：10.1021/jm0101702

  日期：2001.10.1

  The elevated expression of cell adhesion molecules (CAMs) on the lumenal surface of vascular endothelial cells is a critical early event in the complex inflammatory process. The adhesive interactions of these CAMs that include E-selectin, ICAM-1, and VCAM-1 with their counterreceptors on leukocytes, such as integrins of the alpha (L)beta (2) family, result in migration of the leukocytes to the site of inflammation and cause tissue injury. Pharmaceutical agents that could suppress the induced expression of one or more of these cell adhesion molecules would provide a novel mechanism to attenuate the inflammatory responses associated with chronic inflammatory diseases. A-205804 (1), a potent and selective inhibitor of the induced expression of E-selectin and ICAM-1 over VCAM-1, was further modified with emphasis at the C-4 and C-2 positions to identify a more potent drug candidate with a good pharmacokinetic profile and physical properties. Replacement of the C-4 sulfur linkage in I with an oxygen atom eliminated one of the two major metabolites for this lead molecule. The para-position of the 4-phenoxy group of the thieno[2,3-c]pyridine lead is found to be very critical for a higher in vitro potency and selectivity of E-selectin and ICAM-1 over VCAM-1 expression. This position is presumably close to the solvent-accessible region of the target protein-inhibitor complex. An attempt to install a water-solubilizing group at the para-position of the phenoxy group to increase the aqueous solubility of this lead series through various linkages failed to provide an ideal inhibitor. Only small substituents such as fluorine are tolerated at the meta- and ortho-positions of the 4-phenoxy to retain a good in vitro potency. Bromo, trifluoromethyl, pyrazol-1-yl, and imidazol-1-yl are among the better substituents at the para-position. With fine-tuning at the C-2 position we discovered a series of very potent (IC50 < 5 nM for ICAM-1) and selective (> 200-fold vs VCAM-1) inhibitors with a good pharmacokinetic profile. Demonstrated efficacy in a rat rheumatoid arthritis model and in a mice asthma model with selected compounds is also reported.
• Metalation of phenols. Synthesis of benzoquinones by the oxidative degradation approach
  作者：Jose M. Saa、Antonia Llobera、Angel Garcia-Raso、Antonio Costa、Pedro M. Deya

  DOI：10.1021/jo00253a019

  日期：1988.9
• CELL ADHESION-INHIBITING ANTINFLAMMATORY COMPOUNDS
  申请人：ABBOTT LABORATORIES

  公开号：EP1090009A2

  公开（公告）日：2001-04-11