(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]benzopyran-1-yl trifluoromethanesulfonate | 1219610-88-4

• 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]benzopyran-1-yl trifluoromethanesulfonate
• 英文别名: (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-1-yl trifluoromethanesulfonate；(6aR,10aR)-6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-yl trifluoromethanesulfonate；[(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-yl] trifluoromethanesulfonate
• CAS: 1219610-88-4
• 化学式: C₂₂H₂₉F₃O₄S
• 分子量: 446.531
• InChiKey: AHZCIOWJNHBMMD-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  7

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]benzopyran-1-yl trifluoromethanesulfonate 在 二苯甲酮亚胺 、 palladium diacetate 、 caesium carbonate 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 、 盐酸 、 水 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-amine
  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：

  三氟甲磺酸酐 、 四氢大麻酚 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]benzopyran-1-yl trifluoromethanesulfonate
  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

文献信息

• FLUORINATION OF ORGANIC COMPOUNDS
  申请人：Ritter Tobias

  公开号：US20110312903A1

  公开（公告）日：2011-12-22

  Methods for fluorinating organic compounds are described herein.

  本文描述了有机化合物氟化的方法。
• US9024093B2
  申请人：——

  公开号：US9024093B2

  公开（公告）日：2015-05-05
• Synthesis and structure–activity relationship of substitutions at the C-1 position of Δ9-tetrahydrocannabinol
  作者：David Burdick、Russell DeOrazio、Peter Guzzo、Alicia Habershaw、Mark Helle、Bernard Paul、Mark Wolf

  DOI：10.1016/j.bmcl.2009.12.092

  日期：2010.2

  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.