3-(5-phenoxy-1,1-dimethylpentyl)methoxybenzene

• 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: 3-(5-phenoxy-1,1-dimethylpentyl)methoxybenzene
• 英文别名: 1-Methoxy-3-(2-methyl-6-phenoxyhexan-2-yl)benzene；1-methoxy-3-(2-methyl-6-phenoxyhexan-2-yl)benzene
• 化学式: C₂₀H₂₆O₂
• 分子量: 298.425
• InChiKey: BDBCNTZWOIBUAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(5-phenoxy-1,1-dimethylpentyl)methoxybenzene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到3-(5-bromo-1,1-dimethylpentyl)phenol
  参考文献：
  名称：

  Novel, potent THC/anandamide (hybrid) analogs

  摘要：

  The structure-activity relationship (SAR) of the end pentyl chain in anandamide (AEA) has been established to be very similar to that of Delta(9)-tetrahydrocannabinol (Delta(9)-THC). In order to broaden our understanding of the structural similarities between AEA and THC, hybrid structures 1-3 were designed. In these hybrids the aromatic ring of THC-DMH was linked to the AEA moiety through an ether linkage with the oxygen of the phenol of THC. Hybrid 1 (O-2220) was found to have very high binding affinity to CB1 receptors (K-i = 8.5 nM), and it is interesting to note that the orientation of the side chain with respect to the oxygen in the phenol is the same as in THCs. To further explore the SAR in this series the terminal carbon of the side chain was modified by adding different substituents. Several such analogs were synthesized and tested for their CB1 and CB2 binding affinities and in vivo activity (tetrad tests). The details of the synthesis and the biological activity of these compounds are described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.08.039
• 作为产物：
  描述：

  1-(3-methoxyphenyl)-5-phenoxypentan-1-one 、 Dimethylzinc 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以60%的产率得到3-(5-phenoxy-1,1-dimethylpentyl)methoxybenzene
  参考文献：
  名称：

  Novel, potent THC/anandamide (hybrid) analogs

  摘要：

  The structure-activity relationship (SAR) of the end pentyl chain in anandamide (AEA) has been established to be very similar to that of Delta(9)-tetrahydrocannabinol (Delta(9)-THC). In order to broaden our understanding of the structural similarities between AEA and THC, hybrid structures 1-3 were designed. In these hybrids the aromatic ring of THC-DMH was linked to the AEA moiety through an ether linkage with the oxygen of the phenol of THC. Hybrid 1 (O-2220) was found to have very high binding affinity to CB1 receptors (K-i = 8.5 nM), and it is interesting to note that the orientation of the side chain with respect to the oxygen in the phenol is the same as in THCs. To further explore the SAR in this series the terminal carbon of the side chain was modified by adding different substituents. Several such analogs were synthesized and tested for their CB1 and CB2 binding affinities and in vivo activity (tetrad tests). The details of the synthesis and the biological activity of these compounds are described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.08.039

文献信息

• CANNABINERGIC NITRATE ESTERS AND RELATED ANALOGS
  申请人：Northeastern University

  公开号：US20160002195A1

  公开（公告）日：2016-01-07

  The present technology relates to novel cannabinergic nitrate esters and related analogs, process of preparation, pharmaceutical compositions and their methods of use as medicaments, pharmacological tools and/or biomarkers. The novel cannabinergic nitrate ester compounds provide medicaments useful in treating a variety of diseases and medical disorders.

  本技术涉及新型大麻素硝酸酯及其类似物、制备方法、制药组合物及其作为药物、药理工具和/或生物标志物的使用方法。这些新型大麻素硝酸酯化合物提供了治疗各种疾病和医学障碍的有用药物。
• Cannabinergic nitrate esters and related analogs
  申请人：Northeastern University

  公开号：US10221164B2

  公开（公告）日：2019-03-05

  The present technology relates to novel cannabinergic nitrate esters and related analogs, process of preparation, pharmaceutical compositions and their methods of use as medicaments, pharmacological tools and/or biomarkers. The novel cannabinergic nitrate ester compounds provide medicaments useful in treating a variety of diseases and medical disorders.

  本技术涉及新型大麻素能硝酸酯和相关类似物、制备工艺、药物组合物及其作为药物、药理学工具和/或生物标记物的使用方法。新型大麻素能硝酸酯化合物可提供治疗各种疾病和医学紊乱的药物。
• Cannabinergic Nitrate Esters And Related Analogs
  申请人：Northeastern University

  公开号：US20170210728A1

  公开（公告）日：2017-07-27

  The present technology relates to novel cannabinergic nitrate esters and related analogs, process of preparation, pharmaceutical compositions and their methods of use as medicaments, pharmacological tools and/or biomarkers. The novel cannabinergic nitrate ester compounds provide medicaments useful in treating a variety of diseases and medical disorders.
• US9580400B2
  申请人：——

  公开号：US9580400B2

  公开（公告）日：2017-02-28
• [EN] CANNABINERGIC NITRATE ESTERS AND RELATED ANALOGS<br/>[FR] NITRO-ESTERS CANNABINERGIQUES ET ANALOGUES ASSOCIÉS
  申请人：UNIV NORTHEASTERN

  公开号：WO2014134127A1

  公开（公告）日：2014-09-04

  The present technology relates to novel cannabinergic nitrate esters and related analogs, process of preparation, pharmaceutical compositions and their methods of use as medicaments, pharmacological tools and/or biomarkers. The novel cannabinergic nitrate ester compounds provide medicaments useful in treating a variety of diseases and medical disorders.