2-benzyl-1-(2-bromoethoxy)-4-chlorobenzene | 68032-82-6

• 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: 2-benzyl-1-(2-bromoethoxy)-4-chlorobenzene
• CAS: 68032-82-6
• 化学式: C₁₅H₁₄BrClO
• 分子量: 325.633
• InChiKey: WKZYCEUFSSVDFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-benzyl-1-(2-bromoethoxy)-4-chlorobenzene 、 尿嘧啶 在 氯化铵 、 六甲基二硅氮烷 作用下， 反应 5.5h， 以97%的产率得到1-(2-(2-benzyl-4-chlorophenoxy)ethyl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  [EN] CATECHOL DIETHERS AS POTENT ANTI-HIV AGENTS
  [FR] DIÉTHERS DE CATÉCHOL COMME AGENTS ANTI-HIV PUISSANTS

  摘要：

  公开号：

  WO2013056003A3
• 作为产物：
  描述：

  4-氯-2-苄基苯酚 、 2-溴乙醇 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 24.17h， 以67%的产率得到2-benzyl-1-(2-bromoethoxy)-4-chlorobenzene
  参考文献：
  名称：

  Computationally-Guided Optimization of a Docking Hit to Yield Catechol Diethers as Potent Anti-HIV Agents

  摘要：

  A 5-mu M docking hit has been optimized to an extraordinarily potent (55 pM) non-nucleoside inhibitor of HIV reverse transcriptase. Use of free energy perturbation (PEP) calculations to predict relative free energies of binding aided the optimizations by identifying optimal substitution patterns for phenyl rings and a linker. The most potent resultant catechol diethers feature terminal uracil and cyanovinylphenyl groups. A halogen bond with Pro95 likely contributes to the extreme potency of compound 42. In addition, several examples are provided illustrating failures of attempted grafting of a substructure from a very active compound onto a seemingly related scaffold to improve its activity.

  DOI：

  10.1021/jm201134m

文献信息

• TURAEVA M. K.; AXMEDOV K. N.; ABDURASULEVA A. R., SB. NAUCH. TR. TASHKENT. YH-T, 1976, HO 513, 51-56
  作者：TURAEVA M. K.、 AXMEDOV K. N.、 ABDURASULEVA A. R.

  DOI：——

  日期：——
• Computationally-Guided Optimization of a Docking Hit to Yield Catechol Diethers as Potent Anti-HIV Agents
  作者：Mariela Bollini、Robert A. Domaoal、Vinay V. Thakur、Ricardo Gallardo-Macias、Krasimir A. Spasov、Karen S. Anderson、William L. Jorgensen

  DOI：10.1021/jm201134m

  日期：2011.12.22

  A 5-mu M docking hit has been optimized to an extraordinarily potent (55 pM) non-nucleoside inhibitor of HIV reverse transcriptase. Use of free energy perturbation (PEP) calculations to predict relative free energies of binding aided the optimizations by identifying optimal substitution patterns for phenyl rings and a linker. The most potent resultant catechol diethers feature terminal uracil and cyanovinylphenyl groups. A halogen bond with Pro95 likely contributes to the extreme potency of compound 42. In addition, several examples are provided illustrating failures of attempted grafting of a substructure from a very active compound onto a seemingly related scaffold to improve its activity.
• [EN] CATECHOL DIETHERS AS POTENT ANTI-HIV AGENTS<br/>[FR] DIÉTHERS DE CATÉCHOL COMME AGENTS ANTI-HIV PUISSANTS
  申请人：UNIV YALE

  公开号：WO2013056003A3

  公开（公告）日：2013-06-20