4-[[(1,1’-dimethyl)dimethylsilyl]oxy]-α-phenyl-benzenemethanol | 948044-23-3

• 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: 4-[[(1,1’-dimethyl)dimethylsilyl]oxy]-α-phenyl-benzenemethanol
• 英文别名: [4-[(tert-butyldimethylsilyl)oxy]phenyl](phenyl)methanol；[4-[Tert-butyl(dimethyl)silyl]oxyphenyl]-phenylmethanol；[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-phenylmethanol
• CAS: 948044-23-3
• 化学式: C₁₉H₂₆O₂Si
• 分子量: 314.5
• InChiKey: QHSFMFPUUKDEJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 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-[[(1,1’-dimethyl)dimethylsilyl]oxy]-α-phenyl-benzenemethanol 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以95%的产率得到4-hydroxy-benzhydrol
  参考文献：
  名称：

  Acetoxybenzhydrols as highly active and stable analogues of 1′S-1′-acetoxychavicol, a potent antiallergic principal from Alpinia galanga

  摘要：

  Through SAR studies on 1'S-1'-acetoxychavicol acetate (1) against Type I antiallergic activity by indexing release of beta-hexosaminidase, a marker of antigen-IgE-mediated degranulation in RBL-2H3 cells, more stable and potent analogue, 4-(methoxycarbonyloxyphenylmethyl) phenyl acetate (16), has been developed. The compound 16 also strongly inhibited the antigen-IgE-mediated TNF-alpha and IL-4 production. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.065
• 作为产物：
  描述：

  (4-(叔-丁基二甲基硅烷基氧基)苯基)苯基甲酮 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以60%的产率得到4-[[(1,1’-dimethyl)dimethylsilyl]oxy]-α-phenyl-benzenemethanol
  参考文献：
  名称：

  Acetoxybenzhydrols as highly active and stable analogues of 1′S-1′-acetoxychavicol, a potent antiallergic principal from Alpinia galanga

  摘要：

  Through SAR studies on 1'S-1'-acetoxychavicol acetate (1) against Type I antiallergic activity by indexing release of beta-hexosaminidase, a marker of antigen-IgE-mediated degranulation in RBL-2H3 cells, more stable and potent analogue, 4-(methoxycarbonyloxyphenylmethyl) phenyl acetate (16), has been developed. The compound 16 also strongly inhibited the antigen-IgE-mediated TNF-alpha and IL-4 production. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.04.065

文献信息

• A Nickel Catalyst for the Addition of Organoboronate Esters to Ketones and Aldehydes
  作者：Jean Bouffard、Kenichiro Itami

  DOI：10.1021/ol9017613

  日期：2009.10.1

  Ni(cod)2/IPr catalyst promotes the intermolecular 1,2-addition of arylboronate esters to unactivated aldehydes and ketones. Diaryl, alkyl aryl, and dialkyl ketones show good reactivity under mild reaction conditions (≤80 °C, nonpolar solvents, no strong base or acid additives). A dramatic ligand effect favors either carbonyl addition (IPr) or C−OR cross-coupling (PCy3) with aryl ether substrates. A Ni(0)/Ni(II)

  Ni（cod）2 / IPr催化剂可促进芳基硼酸酯的分子间1，2-加成至未活化的醛和酮。二芳基，烷基芳基和二烷基酮在温和的反应条件下（≤80°C，非极性溶剂，无强碱或强酸添加剂）显示出良好的反应活性。显着的配体效应有利于羰基加成（IPr）或与芳基醚底物的C-OR交叉偶联（PCy 3）。提出了由羰基底物的氧化环化引发的Ni（0）/ Ni（II）催化循环。
• Synthesis, Biological Evaluation, and Docking Studies of Antagonistic Hydroxylated Arecaidine Esters Targeting mAChRs
  作者：Jonas Kilian、Marlon Millard、Marius Ozenil、Dominik Krause、Khadija Ghaderi、Wolfgang Holzer、Ernst Urban、Helmut Spreitzer、Wolfgang Wadsak、Marcus Hacker、Thierry Langer、Verena Pichler

  DOI：10.3390/molecules27103173

  日期：——

  The muscarinic acetylcholine receptor family is a highly sought-after target in drug and molecular imaging discovery efforts aimed at neurological disorders. Hampered by the structural similarity of the five subtypes’ orthosteric binding pockets, these efforts largely failed to deliver subtype-selective ligands. Building on our recent successes with arecaidine-derived ligands targeting M1, herein we

  毒蕈碱乙酰胆碱受体家族是针对神经系统疾病的药物和分子成像发现工作中备受追捧的目标。由于五种亚型的正构结合口袋的结构相似性，这些努力在很大程度上未能提供亚型选择性配体。基于我们最近在靶向 M 1的槟榔衍生配体方面取得的成功，我们在此报告了一系列相关的 11 羟基化槟榔酯的合成。它们的物理化学特性曲线，以其计算计算的 CNS MPO 分数和 HPLC-logD 值表示，指向血脑屏障渗透性。通过竞争性放射性配体结合测定，对每个人 mAChR 亚型h的结合亲和力值M 1 – h M 5已确定。该系列17b中最有希望的化合物显示出在个位数纳摩尔区域 (5.5 nM)对h M 1具有结合常数。与我们之前报道的槟榔衍生酯类似，整个系列显示在钙通量测定中充当h M1R 拮抗剂。总体而言，这项研究极大地扩展了我们对这种反复出现的支架结构-活性关系的理解，并将指导向高选择性 mAChRs 配体的发展。
• 10.1002/ejoc.202400474
  作者：Makino, Kosho、Hasebe, Mai、Sueki, Shunsuke、Anada, Masahiro

  DOI：10.1002/ejoc.202400474

  日期：——

  A Brønsted acid-catalyzed, concise and direct cyanation of benzylic alcohols using TMSCN as a cyanide source and HFIP as a solvent has been developed. Through this simple and easy-to-handle method, we have achieved the preparation of intermediates for pharmaceuticals, late-stage material transformations, and a short-step enantioselective synthesis of (S)-verimol F.

  已经开发出一种使用 TMSCN 作为氰化物源、HFIP 作为溶剂的布朗斯台德酸催化、简洁、直接的苯甲醇氰化方法。通过这种简单易操作的方法，我们实现了药物中间体的制备、后期材料转化以及(S)-verimol F的短步骤对映选择性合成。
• Diaryl hydroxylamines as pan or dual inhibitors of indoleamine 2,3-dioxygenase-1, indoleamine 2,3-dioxygenase-2 and tryptophan dioxygenase
  作者：Maria Winters、James B. DuHadaway、Khoa N. Pham、Ariel Lewis-Ballester、Shorouk Badir、Jenny Wai、Eesha Sheikh、Syun-Ru Yeh、George C. Prendergast、Alexander J. Muller、William P. Malachowski

  DOI：10.1016/j.ejmech.2018.11.010

  日期：2019.1

  Tryptophan (Trp) catabolizing enzymes play an important and complex role in the development of cancer. Significant evidence implicates them in a range of inflammatory and immunosuppressive activities. Whereas inhibitors of indoleamine 2,3-dioxygenase-1 (IDO1) have been reported and analyzed in the clinic, fewer inhibitors have been described for tryptophan dioxygenase (TDO) and indoleamine 2,3-dioxygenase-2 (IDO2) which also have been implicated more recently in cancer, inflammation and immune control. Consequently the development of dual or pan inhibitors of these Trp catabolizing enzymes may represent a therapeutically important area of research. This is the first report to describe the development of dual and pan inhibitors of IDO1, TDO and IDO2. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Acetoxybenzhydrols as highly active and stable analogues of 1′S-1′-acetoxychavicol, a potent antiallergic principal from Alpinia galanga
  作者：Tomohisa Yasuhara、Yoshiaki Manse、Takayuki Morimoto、Wang Qilong、Hisashi Matsuda、Masayuki Yoshikawa、Osamu Muraoka

  DOI：10.1016/j.bmcl.2009.04.065

  日期：2009.6

  Through SAR studies on 1'S-1'-acetoxychavicol acetate (1) against Type I antiallergic activity by indexing release of beta-hexosaminidase, a marker of antigen-IgE-mediated degranulation in RBL-2H3 cells, more stable and potent analogue, 4-(methoxycarbonyloxyphenylmethyl) phenyl acetate (16), has been developed. The compound 16 also strongly inhibited the antigen-IgE-mediated TNF-alpha and IL-4 production. (C) 2009 Elsevier Ltd. All rights reserved.