(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-1-carbonitrile | 1219610-90-8

• 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-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-1-carbonitrile
• 英文别名: (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromene-1-carbonitrile
• CAS: 1219610-90-8
• 化学式: C₂₂H₂₉NO
• 分子量: 323.478
• InChiKey: MGLIKSZSFISFMY-RTBURBONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-1-carbonitrile 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 ((6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-yl)methanamine
  参考文献：
  名称：

  Synthesis and structure–activity relationship of substitutions at the C-1 position of Δ9-tetrahydrocannabinol

  摘要：

  A novel series of Delta 9-tetrahydrocannabinol (Delta 9-THC) analogues were synthesized to determine their potential as cannabinoid receptor modulators. Chemistry focused on conversion of the phenol of Delta 9-THC to other functionality through palladium catalyzed reactions with an intermediate triflate 2. Two analogues with sub 100 nM affinity for the CB1 and CB2 receptors were identified. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.092
• 作为产物：
  描述：

  zinc(II) cyanide 、 (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]benzopyran-1-yl trifluoromethanesulfonate 在 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-1-carbonitrile
  参考文献：
  名称：

  Synthesis and structure–activity relationship of substitutions at the C-1 position of Δ9-tetrahydrocannabinol

  摘要：

  A novel series of Delta 9-tetrahydrocannabinol (Delta 9-THC) analogues were synthesized to determine their potential as cannabinoid receptor modulators. Chemistry focused on conversion of the phenol of Delta 9-THC to other functionality through palladium catalyzed reactions with an intermediate triflate 2. Two analogues with sub 100 nM affinity for the CB1 and CB2 receptors were identified. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.12.092