1-(2-((tert-butyldimethylsilyl)oxy)-6-hydroxyphenyl)ethanone | 1193107-75-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-((tert-butyldimethylsilyl)oxy)-6-hydroxyphenyl)ethanone
• 英文别名: 1-[2-[Tert-butyl(dimethyl)silyl]oxy-6-hydroxyphenyl]ethanone；1-[2-[tert-butyl(dimethyl)silyl]oxy-6-hydroxyphenyl]ethanone
• CAS: 1193107-75-3
• 化学式: C₁₄H₂₂O₃Si
• 分子量: 266.412
• InChiKey: QZHUOPHSBZFULF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-((tert-butyldimethylsilyl)oxy)-6-hydroxyphenyl)ethanone 在 4-二甲氨基吡啶 、 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 甲苯 、 mineral oil 为溶剂， 反应 11.25h， 生成 3-(benzo[d][1,3]dioxol-5-ylmethyl)-8-hydroxy-1-(thiazol-2-yl)chromeno[2,3-c]pyrrol-9(2H)-one
  参考文献：
  名称：

  作为高效，选择性和口服生物利用性PDE5抑制剂的Chromeno [2,3 - c ] pyrrol -9（2 H）-ones的优化：结构-活性关系，X射线晶体结构以及对肺动脉高压的药效学作用

  摘要：

  为了进一步探索铬诺[2,3 - c ]吡咯-9（2 H）-一个支架周围的结构-活性关系，发现了19种衍生物作为PDE5抑制剂。最有效的抑制剂3的IC 50为0.32 nM，具有显着的选择性和类药物特性。口服3（1.25 mg / kg）与西地那非（10.0 mg / kg）对肺动脉高压的治疗效果相当。此外，在共晶结构中揭示了与昔多芬不同的结合模式，这为发现高效PDE5抑制剂提供了结构模板。

  DOI：

  10.1021/acs.jmedchem.8b01209
• 作为产物：
  描述：

  2,6-二羟基苯乙酮 在 咪唑 、 potassium carbonate 、 zinc(II) chloride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 35.17h， 生成 1-(2-((tert-butyldimethylsilyl)oxy)-6-hydroxyphenyl)ethanone
  参考文献：
  名称：

  Positional chemoselectivity in the Zn(II)-mediated removal of phenol protecting groups

  摘要：

  A protocol was developed for the chemoselective ortho-deprotection of polyphenolic substrates using readily available (ZnX2)-X-II salts. This procedure provides exceptional positional selectivity for the deprotection of phenols that reside adjacent to directing carbonyl functionality in the presence of similar protecting groups at the meta and para positions. Good to excellent yields of the desired free phenols were obtained (<= 96%), and a wide assortment of protecting groups was readily removed under the reaction conditions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.103

文献信息

• Synthetic Studies of Fisetin, Myricetin and Nobiletin Analogs and Related Probe Molecules
  作者：Toshiyuki Kan、Aiki Hiza、Yuta Tsukaguchi、Takahiro Ogawa、Makoto Inai、Tomohiro Asakawa、Yoshitaka Hamashima

  DOI：10.3987/com-13-s(s)107

  日期：——
• Optimization of Chromeno[2,3-<i>c</i>]pyrrol-9(2<i>H</i>)-ones as Highly Potent, Selective, and Orally Bioavailable PDE5 Inhibitors: Structure–Activity Relationship, X-ray Crystal Structure, and Pharmacodynamic Effect on Pulmonary Arterial Hypertension
  作者：Deyan Wu、Yadan Huang、Yiping Chen、Yi-You Huang、Haiju Geng、Tianhua Zhang、Chen Zhang、Zhe Li、Lei Guo、Jianwen Chen、Hai-Bin Luo

  DOI：10.1021/acs.jmedchem.8b01209

  日期：2018.9.27

  To further explore the structure–activity relationship around the chromeno[2,3-c]pyrrol-9(2H)-one scaffold, 19 derivatives as inhibitors against PDE5 were discovered. The most potent inhibitor 3 has an IC50 of 0.32 nM with remarkable selectivity and druglike profile. Oral administration of 3 (1.25 mg/kg) caused comparable therapeutic effects to sildenafil (10.0 mg/kg) against pulmonary arterial hypertension

  为了进一步探索铬诺[2,3 - c ]吡咯-9（2 H）-一个支架周围的结构-活性关系，发现了19种衍生物作为PDE5抑制剂。最有效的抑制剂3的IC 50为0.32 nM，具有显着的选择性和类药物特性。口服3（1.25 mg / kg）与西地那非（10.0 mg / kg）对肺动脉高压的治疗效果相当。此外，在共晶结构中揭示了与昔多芬不同的结合模式，这为发现高效PDE5抑制剂提供了结构模板。
• Positional chemoselectivity in the Zn(II)-mediated removal of phenol protecting groups
  作者：Lauren M. Fleury、Joseph B. Gianino、Brandon L. Ashfeld

  DOI：10.1016/j.tetlet.2012.07.103

  日期：2012.10

  A protocol was developed for the chemoselective ortho-deprotection of polyphenolic substrates using readily available (ZnX2)-X-II salts. This procedure provides exceptional positional selectivity for the deprotection of phenols that reside adjacent to directing carbonyl functionality in the presence of similar protecting groups at the meta and para positions. Good to excellent yields of the desired free phenols were obtained (<= 96%), and a wide assortment of protecting groups was readily removed under the reaction conditions. (C) 2012 Elsevier Ltd. All rights reserved.