(6R,6aR,9R,10aR)-3-(1,1-Dimethyl-heptyl)-9-hydroxymethyl-6-(3-hydroxy-prop-1-ynyl)-6-methyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol | 303113-08-8

• 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: (6R,6aR,9R,10aR)-3-(1,1-Dimethyl-heptyl)-9-hydroxymethyl-6-(3-hydroxy-prop-1-ynyl)-6-methyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol
• 英文别名: 6H-Dibenzo(b,d)pyran-9-methanol, 3-(1,1-dimethylheptyl)-6a,7,8,9,10,10a-hexahydro-1-hydroxy-6-(3-hydroxy-1-propynyl)-6-methyl-, (6R,6aR,9R,10aR)-rel-；(6R,6aR,9R,10aR)-9-(hydroxymethyl)-6-(3-hydroxyprop-1-ynyl)-6-methyl-3-(2-methyloctan-2-yl)-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol
• CAS: 303113-08-8
• 化学式: C₂₇H₄₀O₄
• 分子量: 428.612
• InChiKey: FFRHKSZKZQWCOY-UOTIDGTBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (6R,6aR,9R,10aR)-3-(1,1-Dimethyl-heptyl)-9-hydroxymethyl-6-(3-hydroxy-prop-1-ynyl)-6-methyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol 在 Lindlar's catalyst 喹啉 、 氢气 作用下， 以 苯 为溶剂， 反应 2.0h， 以91%的产率得到(6S,6aR,9R,10aR)-3-(1,1-Dimethyl-heptyl)-9-hydroxymethyl-6-((Z)-3-hydroxy-propenyl)-6-methyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol
  参考文献：
  名称：

  Synthesis of Functionalized Cannabinoids

  摘要：

  An effective synthesis. of tricyclic, nonclassical cannabinoids has been developed on the basis of a cation-olefin cyclization that forms the two nonaromatic rings with the desired stereochemistry in a single step.

  DOI：

  10.1021/jo000716c
• 作为产物：
  描述：

  (6R,6aR,9R,10aR)-6-[3-(tert-Butyl-dimethyl-silanyloxy)-prop-1-ynyl]-3-(1,1-dimethyl-heptyl)-9-hydroxymethyl-6-methyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol 在 triethylamine trihydrofluoride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以96%的产率得到(6R,6aR,9R,10aR)-3-(1,1-Dimethyl-heptyl)-9-hydroxymethyl-6-(3-hydroxy-prop-1-ynyl)-6-methyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol
  参考文献：
  名称：

  Synthesis of Functionalized Cannabinoids

  摘要：

  An effective synthesis. of tricyclic, nonclassical cannabinoids has been developed on the basis of a cation-olefin cyclization that forms the two nonaromatic rings with the desired stereochemistry in a single step.

  DOI：

  10.1021/jo000716c

文献信息

• Synthesis of Functionalized Cannabinoids
  作者：Paul E. Harrington、Ioanna A. Stergiades、Joy Erickson、Alexandros Makriyannis、Marcus A. Tius

  DOI：10.1021/jo000716c

  日期：2000.10.1

  An effective synthesis. of tricyclic, nonclassical cannabinoids has been developed on the basis of a cation-olefin cyclization that forms the two nonaromatic rings with the desired stereochemistry in a single step.