1-[3,5-Dihydroxy-4-((1R,6R)-6-isopropenyl-3-methyl-cyclohex-2-enyl)-phenyl]-cyclohexanecarbonitrile | 881888-35-3

• 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: 1-[3,5-Dihydroxy-4-((1R,6R)-6-isopropenyl-3-methyl-cyclohex-2-enyl)-phenyl]-cyclohexanecarbonitrile
• 英文别名: 1-[3,5-dihydroxy-4-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]phenyl]cyclohexane-1-carbonitrile
• CAS: 881888-35-3
• 化学式: C₂₃H₂₉NO₂
• 分子量: 351.489
• InChiKey: OEQJXSVWDWNCHK-RBUKOAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  64.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[3,5-Dihydroxy-4-((1R,6R)-6-isopropenyl-3-methyl-cyclohex-2-enyl)-phenyl]-cyclohexanecarbonitrile 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 1-((6aR,10aR)-1-Hydroxy-6,6,9-trimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-3-yl)-cyclohexanecarbonitrile
  参考文献：
  名称：

  Structural modifications of the cannabinoid side chain towards C3-aryl and 1′,1′-cycloalkyl-1′-cyano cannabinoids

  摘要：

  The compounds reported in this study are Delta(8)-THC analogues in which the C3 five-carbon linear side chain of Delta(8)-THC was replaced with aryl and 1',1'-cycloalkyl substituents. Of the compounds described here analogues 2d (CB1, K-i = 11.7 nM. CB2, K-i = 9.39 nM) and 2f (CB1, K-i = 8.26 nM. CB2, K-i = 3.86 nM) exhibited enhanced binding affinities for CB1 and CB2, exceeding that of Delta(8)-THC. Efficient procedures for the synthesis of these novel cannabinoid analogues are described. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.026
• 作为产物：
  描述：

  3,5-二甲氧基苯基乙腈 在 三溴化硼 、 双(三甲基硅烷基)氨基钾 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 生成 1-[3,5-Dihydroxy-4-((1R,6R)-6-isopropenyl-3-methyl-cyclohex-2-enyl)-phenyl]-cyclohexanecarbonitrile
  参考文献：
  名称：

  Structural modifications of the cannabinoid side chain towards C3-aryl and 1′,1′-cycloalkyl-1′-cyano cannabinoids

  摘要：

  The compounds reported in this study are Delta(8)-THC analogues in which the C3 five-carbon linear side chain of Delta(8)-THC was replaced with aryl and 1',1'-cycloalkyl substituents. Of the compounds described here analogues 2d (CB1, K-i = 11.7 nM. CB2, K-i = 9.39 nM) and 2f (CB1, K-i = 8.26 nM. CB2, K-i = 3.86 nM) exhibited enhanced binding affinities for CB1 and CB2, exceeding that of Delta(8)-THC. Efficient procedures for the synthesis of these novel cannabinoid analogues are described. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.026

文献信息

• Structural modifications of the cannabinoid side chain towards C3-aryl and 1′,1′-cycloalkyl-1′-cyano cannabinoids
  作者：Demetris P. Papahatjis、Victoria R. Nahmias、Thanos Andreou、Pusheng Fan、Alexandros Makriyannis

  DOI：10.1016/j.bmcl.2005.12.026

  日期：2006.3

  The compounds reported in this study are Delta(8)-THC analogues in which the C3 five-carbon linear side chain of Delta(8)-THC was replaced with aryl and 1',1'-cycloalkyl substituents. Of the compounds described here analogues 2d (CB1, K-i = 11.7 nM. CB2, K-i = 9.39 nM) and 2f (CB1, K-i = 8.26 nM. CB2, K-i = 3.86 nM) exhibited enhanced binding affinities for CB1 and CB2, exceeding that of Delta(8)-THC. Efficient procedures for the synthesis of these novel cannabinoid analogues are described. (C) 2006 Elsevier Ltd. All rights reserved.