4-(Trityloxymethyl)phenol | 228106-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 4-(Trityloxymethyl)phenol
• CAS: 228106-33-0
• 化学式: C₂₆H₂₂O₂
• 分子量: 366.459
• InChiKey: KILVBBKTPXSZBK-UHFFFAOYSA-N

物化性质

• 沸点：
  508.8±45.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(Trityloxymethyl)phenol 在 sodium hydrogen sulfate 、 silica gel 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以93%的产率得到对羟基苯甲醇
  参考文献：
  名称：

  Chemoselective deprotection of trityl ethers using silica-supported sodium hydrogen sulfate

  摘要：

  A highly selective method for the cleavage of trityl ethers over a wide range of functional groups has been developed using silica-supported sodium hydrogen sulfate (NaHSO4-SiO2) as a heterogeneous catalyst. The conversion occurred at room temperature and the yields of the alcohols were found to be excellent. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.07.075
• 作为产物：
  描述：

  对羟基苯甲醇 、 三苯基氯甲烷 在 吡啶 作用下， 反应 2.0h， 以96%的产率得到4-(Trityloxymethyl)phenol
  参考文献：
  名称：

  Novel Para-Substituted Benzyl Ethers for Hydroxyl Group Protection

  摘要：

  DOI：

  10.1021/ja9836085

文献信息

• Cell adhesion-inhibiting antiinflammatory compounds
  申请人：——

  公开号：US20010020030A1

  公开（公告）日：2001-09-06

  Compounds having Formula I 1 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I1式的化合物对于治疗炎症有用。本文还公开了包含I式化合物的制药组合物，以及在哺乳动物中抑制/治疗炎症性疾病的方法。
• 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.
• A Highly Efficient Synthetic Strategy for Polymeric Support Synthesis of Lex, Ley, and H-type 2 Oligosaccharides
  作者：Tong Zhu、Geert-Jan Boons

  DOI：10.1002/1521-3765(20010601)7:11<2382::aid-chem23820>3.0.co;2-2

  日期：2001.6.1

  The O-protecting groups Levulinoyl (Lev) and 9-fluroenylmethoxycarbonyl (Fmoc) offer an attractive set of orthogonal protecting groups which are compatible with base sensitive N-trichloroethoxylcarbonyl (Troc) group. By exploiting these orthogonal protecting groups and a novel phenolic ester linker, a series of oligosaccharide of biological importance, Le(x), H-type 2, and Le(y). were synthesized on the polytheylene glycol resin MPEG (M-w 5000). The products bearing a p-hydroxybenzyl group could be easily converted into glycosyl donors for further synthesis. Using this strategy, a spacer containing tumor antigen Le(y)-Lac hexasaccharide was described. The artificial spacer at the reducing end provides an opportunity for selective conjugation to an appropriate carrier protein for immunlogical studies.
• CELL ADHESION-INHIBITING ANTINFLAMMATORY COMPOUNDS
  申请人：ABBOTT LABORATORIES

  公开号：EP1090009A2

  公开（公告）日：2001-04-11
• CELL ADHESION-INHIBITING ANTIINFLAMMATORY COMPOUNDS
  申请人：ABBOTT LABORATORIES

  公开号：EP1181296A1

  公开（公告）日：2002-02-27