3,5-dimethoxy-1-(2-methyl-6-phenoxyhexan-2-yl)benzene | 215649-01-7

• 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-dimethoxy-1-(2-methyl-6-phenoxyhexan-2-yl)benzene
• 英文别名: 1-phenoxy-5-methyl-5-(3',5'-dimethoxyphenyl)hexane；1-phenoxy-5-(3,5-dimethoxyphenyl)-5,5-dimethylpentane；2-(3,5-Dimethoxyphenyl)-2-methyl-6-phenoxyhexane；1,3-dimethoxy-5-(2-methyl-6-phenoxyhexan-2-yl)benzene
• CAS: 215649-01-7
• 化学式: C₂₁H₂₈O₃
• 分子量: 328.452
• InChiKey: KBJOJAXTNXNDFW-UHFFFAOYSA-N

物化性质

• 沸点：
  457.2±45.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-dimethoxy-1-(2-methyl-6-phenoxyhexan-2-yl)benzene 在 三溴化硼 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 5'-bromo-1',1'-dimethyl-Δ⁸-tetrahydrocannabinol
  参考文献：
  名称：

  Potent Cyano and Carboxamido Side-Chain Analogues of 1‘,1‘-Dimethyl-Δ⁸-Tetrahydrocannabinol

  摘要：

  The synthesis and pharmacological profile of several cyano (1a-e) and carboxamido (2a-h) side-chain-substituted analogues of 1',1'-dimethyl-Delta(8)-THC are described. Commercially available cyano compound 3 was transformed to the resorcinol 6 in a three-step sequence. Condensation of 6 with p-menth-2-ene-1,8-diol formed the THC 7a which, with sodium cyanide/ DMSO, gave Ib. Protection of the phenol in 7a as the MOM derivative provided the common intermediate 8 for the synthesis of 1a,c,e. Compound 1d was also synthesized from 7a via the aldehyde 9a. Base hydrolysis of 1b gave the acid 10 which, via its acid chloride and subsequent treatment with the appropriate amine, formed the target compounds 2a-h. The pharmacological profile indicated that the cyano analogues 1a-e had very high CB1 binding affinity (0.36-13 nM) and high in vivo potency as agonists. Two analogues (1a,b) had extremely high potency in the mouse tetrad tests. The dimethylcarboxamido analogue 2a showed a similar profile to 1a,b. The high potency was also retained in analogue 2c. In contrast the sulfonamide analogue 2d was unique as it had greater affinity than Delta(9)-THC, yet it was practically devoid of agonist effects. This study suggests that the incorporation of a cyano or an amide substituent in the side chain of Delta(8)-THC-DMH can enhance potency and can also lead to compounds with a unique profile which have high binding affinity and are practically devoid of agonist effects.

  DOI：

  10.1021/jm9803875
• 作为产物：
  描述：

  1,3-二甲氧基-5-(5-苯氧基戊基)苯 在 TiCl₄ 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以63%的产率得到3,5-dimethoxy-1-(2-methyl-6-phenoxyhexan-2-yl)benzene
  参考文献：
  名称：

  Water soluble derivatives of cannabinoids

  摘要：

  四氢大麻酚的水溶性酯类化合物，适合在治疗性水基配方中使用，具有以下一般化学式：##STR1## 其中a - - - b表示9(10)或9(8)的双键，R'是一个--(CH.sub.2).sub.n--连接基团，其中n为1-8，R是一个-(CZ.sub.2).sub.n-连接基团，其中n为6或更多，Z独立地为H或类似较低烷基基团的取代基，以及这些化合物的药用可接受盐。

  公开号：

  US05847128A1

文献信息

• [EN] 2-CYCLOALKYL RESORCINOL CANNABINERGIC LIGANDS<br/>[FR] LIGANDS CANNABINERGIQUES DE 2-CYCLOALKYL RÉSORCINOL
  申请人：UNIV NORTHEASTERN

  公开号：WO2014062965A1

  公开（公告）日：2014-04-24

  The present invention relates to novel 2-cycloalkyl resorcinol compounds; to pharmaceutical compositions comprising the compounds; and to methods of preparing the compounds and uses thereof. The disclosed compounds can bind to and modulate the cannabinoid receptors and thus, they are specific ligands for these receptors. The invented compounds, when administered in a therapeutically effective amount to an individual or animal, results in a sufficiently high level of that compound in the individual or animal to cause a physiological response. The physiological response may be useful to treat a number of physiological conditions.

  本发明涉及新型2-环烷基间苯二酚化合物；包括这些化合物的药物组合物；以及制备这些化合物和它们的用途的方法。所披露的化合物可以结合并调节大麻素受体，因此它们是这些受体的特异性配体。当将这些发明的化合物以治疗有效剂量的方式给予个体或动物时，会在个体或动物体内产生足够高水平的该化合物，从而引起生理反应。这种生理反应可能有助于治疗多种生理状况。
• [EN] WATER-SOLUBLE CANNABINOIDS<br/>[FR] CANNABINOIDES SOLUBLES DANS L'EAU
  申请人：UNIV VIRGINIA COMMONWEALTH

  公开号：WO2006012176A1

  公开（公告）日：2006-02-02

  Water-soluble cannabinoid compounds that are agonists of CB1 and CB2 cannabinoid receptors are provided. The compounds are made water-soluble by derivatization of the alkyl side chain and/or the phenolic hydroxyl group of tetrahydrocannabinol. The water-soluble cannabinoids are useful for the treatment of appetite loss, pain, multiple sclerosis, nausea and vomiting, and epilepsy.

  提供了一种可以溶于水的作用于CB1和CB2大麻素受体的大麻素类化合物。通过对四氢大麻酚的烷基侧链和/或酚羟基进行衍生化，使这些化合物可以溶于水。这些水溶性大麻素化合物可用于治疗食欲不振、疼痛、多发性硬化症、恶心和呕吐以及癫痫等疾病。
• 2-CYCLOALKYL RESORCINOL CANNABINERGIC LIGANDS
  申请人：NORTHEASTERN UNIVERSITY

  公开号：US20150274623A1

  公开（公告）日：2015-10-01

  The present invention relates to novel 2-cycloalkyl resorcinol compounds; to pharmaceutical compositions comprising the compounds; and to methods of preparing the compounds and uses thereof. The disclosed compounds can bind to and modulate the cannabinoid receptors and thus, they are specific ligands for these receptors. The invented compounds, when administered in a therapeutically effective amount to an individual or animal, results in a sufficiently high level of that compound in the individual or animal to cause a physiological response. The physiological response may be useful to treat a number of physiological conditions.

  本发明涉及一种新型的2-环烷基邻苯二酚化合物；涉及含有该化合物的药物组合物；以及制备该化合物和使用该化合物的方法。所披露的化合物能够结合和调节大麻素受体，因此它们是这些受体的特异性配体。当以治疗有效量的方式给予这些发明化合物给个体或动物时，会在个体或动物中产生足够高的该化合物水平以引起生理反应。这种生理反应可能有助于治疗许多生理状况。
• Access to “Friedel–Crafts-Restricted” <i>tert</i>-Alkyl Aromatics by Activation/Methylation of Tertiary Benzylic Alcohols
  作者：Joshua A. Hartsel、Derek T. Craft、Qiao-Hong Chen、Ming Ma、Paul R. Carlier

  DOI：10.1021/jo202371c

  日期：2012.4.6

  Herein we describe a two-step protocol to prepare m-tert-alkylbenzenes. The appropriate tertiary benzylic alcohols are activated with SOCl2 or concentrated HCl and then treated with trimethylaluminum, affording the desired products in 68-97% yields (22 examples). This reaction sequence is successful in the presence of a variety of functional groups, including acid-sensitive and Lewis-basic groups. In addition to t-Bu groups, 1,1-dimethylpropyl and 1-ethyl-1-methylpropyl groups can also be installed using this method.
• Water Soluble Cannabinoids
  申请人：Martin Billy R.

  公开号：US20080064679A1

  公开（公告）日：2008-03-13

  Water-soluble cannabinoid compounds that are agonists of CB 1 and CB 2 cannabinoid receptors are provided. The compounds are made water-soluble by derivatization of the alkyl side chain and/or the phenolic hydroxyl group of tetrahydrocannabinol. The water-soluble cannabinoids are useful for the treatment of appetite loss, pain, multiple sclerosis, nausea and vomiting, and epilepsy.