(6aR,10aR)-6,6,9-trimethyl-3-p-tolyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-ol | 939964-57-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (6aR,10aR)-6,6,9-trimethyl-3-p-tolyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-ol
• 英文别名: (6aR,10aR)-6,6,9-trimethyl-3-(4-methylphenyl)-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol
• CAS: 939964-57-5
• 化学式: C₂₃H₂₆O₂
• 分子量: 334.458
• InChiKey: BNNTYBVRZLELKE-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,3-二甲氧基-5-(4-甲基苯基)苯 在 三氟化硼乙醚 、 对甲苯磺酸 、 9-碘-9-硼杂二环[3.3.1]壬烷 作用下， 以 正己烷 、 二氯甲烷 、 苯 为溶剂， 生成 (6aR,10aR)-6,6,9-trimethyl-3-p-tolyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-ol
  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.