2,5-dioxopyrrolidin-1-yl (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-1-carboxylate | 1219610-91-9

• 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: 2,5-dioxopyrrolidin-1-yl (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-1-carboxylate
• CAS: 1219610-91-9
• 化学式: C₂₆H₃₃NO₅
• 分子量: 439.552
• InChiKey: RDBRMXNWVSKLDW-UYAOXDASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.25
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,5-dioxopyrrolidin-1-yl (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-1-carboxylate 在 水 、 三乙胺 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]chromene-1-carboxylic acid
  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：

  N-羟基丁二酰亚胺 、 一氧化碳 、 (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]benzopyran-1-yl trifluoromethanesulfonate 在 palladium diacetate 、 N,N-二异丙基乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 二甲基亚砜 为溶剂， 生成 2,5-dioxopyrrolidin-1-yl (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-1-carboxylate
  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