5-Methoxy-3-tert-butyldiphenylsilyloxyphenol | 960069-08-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-Methoxy-3-tert-butyldiphenylsilyloxyphenol
• 英文别名: 3-[tert-butyl(diphenyl)silyl]oxy-5-methoxyphenol
• CAS: 960069-08-3
• 化学式: C₂₃H₂₆O₃Si
• 分子量: 378.543
• InChiKey: ZRTUXESZVVPUSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Methoxy-3-tert-butyldiphenylsilyloxyphenol 、 E-styryl iodide 在 N-甲基吗啉 、 caesium carbonate 、 copper(l) chloride 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  New classes of Gram-positive selective antibacterials: Inhibitors of MRSA and surrogates of the causative agents of anthrax and tuberculosis

  摘要：

  An antimicrobial phenolic stilbene, (E)-3-hydroxy-5-methoxystilbene, 1 was recently isolated from the leaves of Comptonia peregrina (L.) Coulter and shown to possess inhibitory activity against several Gram-positive bacteria, including isolates of methicillin-resistant Staphylococcus aureus (MRSA), Mycobacterium bovis BCG, and avirulent Bacillus anthracis (Sterne strain), among others. These results prompted the design and synthesis of two new classes of compounds, phenoxystyrenes and phenothiostyrenes, as analogs of the natural antimicrobial stilbene. These and additional stilbenoid analogs were synthesized using new, efficient, copper-mediated coupling strategies. Minimum inhibitory concentration (MIC) antimicrobial assays were performed on all compounds prepared. These preliminary structure-activity relationship studies indicated that both new classes of synthetic analogs, as well as the stilbenes, show promising activity against Gram-positive bacteria when at least one phenolic moiety is present, but not when absent. The potencies of the phenolic phenoxystyrenes and phenothiostyrenes were found to be comparable to those of the phenolic stilbenes tested. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.085
• 作为产物：
  描述：

  夫拉美诺 、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以33%的产率得到5-Methoxy-3-tert-butyldiphenylsilyloxyphenol
  参考文献：
  名称：

  New classes of Gram-positive selective antibacterials: Inhibitors of MRSA and surrogates of the causative agents of anthrax and tuberculosis

  摘要：

  An antimicrobial phenolic stilbene, (E)-3-hydroxy-5-methoxystilbene, 1 was recently isolated from the leaves of Comptonia peregrina (L.) Coulter and shown to possess inhibitory activity against several Gram-positive bacteria, including isolates of methicillin-resistant Staphylococcus aureus (MRSA), Mycobacterium bovis BCG, and avirulent Bacillus anthracis (Sterne strain), among others. These results prompted the design and synthesis of two new classes of compounds, phenoxystyrenes and phenothiostyrenes, as analogs of the natural antimicrobial stilbene. These and additional stilbenoid analogs were synthesized using new, efficient, copper-mediated coupling strategies. Minimum inhibitory concentration (MIC) antimicrobial assays were performed on all compounds prepared. These preliminary structure-activity relationship studies indicated that both new classes of synthetic analogs, as well as the stilbenes, show promising activity against Gram-positive bacteria when at least one phenolic moiety is present, but not when absent. The potencies of the phenolic phenoxystyrenes and phenothiostyrenes were found to be comparable to those of the phenolic stilbenes tested. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.085
• 作为试剂：
  描述：

  叔丁基二苯基氯硅烷 、 夫拉美诺 、 咪唑 在 氩 、 乙酸乙酯 、 盐酸 、 Brine 、 Sodium sulfate-III 、 5-Methoxy-3-tert-butyldiphenylsilyloxyphenol 、 silica gel 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 0.17h， 以to afford pure silyl phenol 19 (892 mg, 33%)的产率得到5-Methoxy-3-tert-butyldiphenylsilyloxyphenol
  参考文献：
  名称：

  ANTI-INFECTIVE AGENTS AND METHODS OF USE

  摘要：

  本发明提供化合物及其使用方法作为抗感染剂。在一种优选实施例中，本发明提供其中R1不是H时，R2是H，且R2不是H时，R1是H，进一步地，其中R1是CH（2n+1）O，其中n为1-10；其中R2是OH或CH（2n+1）O，其中n为1-10；以及其中A、B和R1、R2、R5、R6和R7分别独立地选自H、烷基和芳基基团，而R11是烷基或芳基基团。

  公开号：

  US20070292545A1

文献信息

• Broad Spectrum Gram-Positive Antimicrobials and Anthelmintics with Efficacy Against Drug-Resistant Strains and Mycobacterium Species
  申请人：Monte Aaron P.

  公开号：US20110092578A1

  公开（公告）日：2011-04-21

  The present invention provides compounds and methods of using of the compounds as anti-infective and anthelminitc agents. In a preferred embodiment, the present invention provides the following compound of Formula III: wherein: R 1 is not H when R 2 is H and R 2 is not H when R 1 is H, further wherein R 1 is OH or CH (2n+1) O, wherein n is 1-10; R 2 is OH or CH (2n+1) O, where n is 1-10; W is alkyl, phenyl, halophenyl, pyridyl, piperidyl, or a substituted or unsubstituted aryl group, including unsubstituted and substituted aromatic heterocycles; and L is an optional linker or linking group selected from O, S, NH, CF 2 , or CH 2 , and x=0 or 1, i.e., if x=0, no linking group is present.

  本发明提供了化合物及其使用方法，作为抗感染和驱虫剂。在一种优选实施例中，本发明提供以下III式化合物：其中：当R2为H时，R1不是H，当R1为H时，R2不是H，进一步地，其中R1为OH或CH（2n+1）O，其中n为1-10；R2为OH或CH（2n+1）O，其中n为1-10；W为烷基、苯基、卤代苯基、吡啶基、哌啶基或取代或未取代的芳基基团，包括未取代和取代的芳香杂环；L是可选的连接或连接基，选择自O、S、NH、CF2或CH2，x=0或1，即如果x=0，则不存在连接基。
• Broad spectrum gram-positive antimicrobials and anthelmintics with efficacy against drug-resistant strains and Mycobacterium species
  申请人：Monte Aaron P.

  公开号：US08530512B2

  公开（公告）日：2013-09-10

  The present invention provides compounds and methods of using of the compounds as anti-infective and anthelminitc agents. In a preferred embodiment, the present invention provides the following compound of Formula III: wherein: R1 is not H when R2 is H and R2 is not H when R1 is H, further wherein R1 is OH or CH(2n+1)O, wherein n is 1-10; R2 is OH or CH(2n+1)O, where n is 1-10; W is alkyl, phenyl, halophenyl, pyridyl, piperidyl, or a substituted or unsubstituted aryl group, including unsubstituted and substituted aromatic heterocycles; and L is an optional linker or linking group selected from O, S, NH, CF2, or CH2, and x=0 or 1, i.e., if x=0, no linking group is present and when x=0, W is not phenyl.

  本发明提供了化合物及其使用方法，作为抗感染和抗蛔虫药物。在一种优选实施例中，本发明提供了以下III式化合物：其中：当R2为H时，R1不是H，当R1为H时，R2不是H，进一步地，其中R1为OH或CH（2n+1）O，其中n为1-10；R2为OH或CH（2n+1）O，其中n为1-10；W为烷基，苯基，卤代苯基，吡啶基，哌啶基或取代或未取代芳基基团，包括未取代和取代的芳香杂环；L是可选的连接器或连接基团，选自O，S，NH，CF2或CH2，x=0或1，即如果x=0，则没有连接基团存在，当x=0时，W不是苯基。
• New classes of Gram-positive selective antibacterials: Inhibitors of MRSA and surrogates of the causative agents of anthrax and tuberculosis
  作者：M. Shahjahan Kabir、Kathleen Engelbrecht、Rebecca Polanowski、Sarah M. Krueger、Rachel Ignasiak、Marc Rott、William R. Schwan、Mary E. Stemper、Kurt D. Reed、David Sherman、James M. Cook、Aaron Monte

  DOI：10.1016/j.bmcl.2008.09.085

  日期：2008.11

  An antimicrobial phenolic stilbene, (E)-3-hydroxy-5-methoxystilbene, 1 was recently isolated from the leaves of Comptonia peregrina (L.) Coulter and shown to possess inhibitory activity against several Gram-positive bacteria, including isolates of methicillin-resistant Staphylococcus aureus (MRSA), Mycobacterium bovis BCG, and avirulent Bacillus anthracis (Sterne strain), among others. These results prompted the design and synthesis of two new classes of compounds, phenoxystyrenes and phenothiostyrenes, as analogs of the natural antimicrobial stilbene. These and additional stilbenoid analogs were synthesized using new, efficient, copper-mediated coupling strategies. Minimum inhibitory concentration (MIC) antimicrobial assays were performed on all compounds prepared. These preliminary structure-activity relationship studies indicated that both new classes of synthetic analogs, as well as the stilbenes, show promising activity against Gram-positive bacteria when at least one phenolic moiety is present, but not when absent. The potencies of the phenolic phenoxystyrenes and phenothiostyrenes were found to be comparable to those of the phenolic stilbenes tested. (C) 2008 Elsevier Ltd. All rights reserved.
• ANTI-INFECTIVE AGENTS AND METHODS OF USE
  申请人：Monte Aaron

  公开号：US20070292545A1

  公开（公告）日：2007-12-20

  The present invention provides compounds and methods of using of the compounds as anti-infective agents. In a preferred embodiment, the present invention provides wherein R 1 is not H when R 2 is H and R 2 is not H when R 1 is H, further wherein R 1 is CH (2n+1) O, wherein n is 1-10; wherein R 2 is OH or CH (2n+1) O, wherein n is 1-10; and wherein A, B and R 1 , R 2 , R 5 , R 6 , and R 7 are independently selected from a group consisting of H, alkyl and aryl groups and R 11 is an alkyl or an aryl group

  本发明提供化合物及其使用方法作为抗感染剂。在一种优选实施例中，本发明提供其中R1不是H时，R2是H，且R2不是H时，R1是H，进一步地，其中R1是CH（2n+1）O，其中n为1-10；其中R2是OH或CH（2n+1）O，其中n为1-10；以及其中A、B和R1、R2、R5、R6和R7分别独立地选自H、烷基和芳基基团，而R11是烷基或芳基基团。