methanesulfonic acid (6aSR,10aSR)-6a-cyano-8,9-dimethyl-6-oxo-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-2-yl ester

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 3,4-二氢香豆素
• 英文名称: methanesulfonic acid (6aSR,10aSR)-6a-cyano-8,9-dimethyl-6-oxo-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-2-yl ester
• 英文别名: [(6aS,10aS)-6a-cyano-8,9-dimethyl-6-oxo-10,10a-dihydro-7H-benzo[c]chromen-2-yl] methanesulfonate
• 化学式: C₁₇H₁₇NO₅S
• 分子量: 347.392
• InChiKey: IAUKFQCFPLEPBD-WMLDXEAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methanesulfonic acid 3-cyano-2-oxo-2H-chromen-6-yl ester 、 2,3-二甲基-1,3-丁二烯 以 乙腈 为溶剂， 55.0 ℃ 、1100.02 MPa 条件下， 反应 20.0h， 以75%的产率得到methanesulfonic acid (6aSR,10aSR)-6a-cyano-8,9-dimethyl-6-oxo-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-2-yl ester
  参考文献：
  名称：

  High Pressure Diels−Alder Approach to Hydroxy-Substituted 6a-Cyano-tetrahydro-6H-benzo[c]chromen-6-ones: A Route to Δ⁶-Cis-Cannabidiol

  摘要：

  Diels-Alder cycloaddition reactions of 3-cyanocoumarin, hydroxy-substituted 3-cyanocoumarins and mesyl-substituted 3-cyano-coumarins with methyl-1,3-butadienes carried out under high pressure (11 kbar) are reported. Activation by high pressure allows these reactions to proceed satisfactorily under mild conditions to produce 6a-cyano-hydroxy- and 6a-cyano-mesyl-tetrahydro-6H-benzo[c]chromen-6-ones in moderate to excellent yield. The synthesis of cis-1-hydroxy-9-methyl-3-pentyl-6a,7, 10,10a-tetrahydro-benzo[c]chromen-6-one as precursor of Delta(6)-3,4-cis-cannabidiol (Delta(6)-cis-CBD) and Delta(8)-cis-tetrahydrocannabinol (Delta(8)-cis-THC) is outlined.

  DOI：

  10.1021/jo9005365

文献信息

• High Pressure Diels−Alder Approach to Hydroxy-Substituted 6a-Cyano-tetrahydro-6H-benzo[c]chromen-6-ones: A Route to Δ⁶-<i>Cis</i>-Cannabidiol
  作者：Eleonora Ballerini、Lucio Minuti、Oriana Piermatti、Ferdinando Pizzo

  DOI：10.1021/jo9005365

  日期：2009.6.5

  Diels-Alder cycloaddition reactions of 3-cyanocoumarin, hydroxy-substituted 3-cyanocoumarins and mesyl-substituted 3-cyano-coumarins with methyl-1,3-butadienes carried out under high pressure (11 kbar) are reported. Activation by high pressure allows these reactions to proceed satisfactorily under mild conditions to produce 6a-cyano-hydroxy- and 6a-cyano-mesyl-tetrahydro-6H-benzo[c]chromen-6-ones in moderate to excellent yield. The synthesis of cis-1-hydroxy-9-methyl-3-pentyl-6a,7, 10,10a-tetrahydro-benzo[c]chromen-6-one as precursor of Delta(6)-3,4-cis-cannabidiol (Delta(6)-cis-CBD) and Delta(8)-cis-tetrahydrocannabinol (Delta(8)-cis-THC) is outlined.