2,2-Dimethyl-propionic acid (6aR,10aR)-3-((1S,2R)-1,2-dimethyl-heptyl)-1-hydroxy-6,6-dimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-9-ylmethyl ester

• 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: 2,2-Dimethyl-propionic acid (6aR,10aR)-3-((1S,2R)-1,2-dimethyl-heptyl)-1-hydroxy-6,6-dimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-9-ylmethyl ester
• 英文别名: [(6aR,10aR)-1-hydroxy-6,6-dimethyl-3-[(2S,3R)-3-methyloctan-2-yl]-6a,7,10,10a-tetrahydrobenzo[c]chromen-9-yl]methyl 2,2-dimethylpropanoate
• 化学式: C₃₀H₄₆O₄
• 分子量: 470.693
• InChiKey: UCAHKXHEAKKTEV-WNXIRNOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-propionic acid (6aR,10aR)-3-((1S,2R)-1,2-dimethyl-heptyl)-1-hydroxy-6,6-dimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-9-ylmethyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到(6aR,10aR)-3-((1S,2R)-1,2-Dimethyl-heptyl)-9-hydroxymethyl-6,6-dimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-ol
  参考文献：
  名称：

  Enantioselective synthesis and pharmacology of 11-hydroxy-(1'S,2'R)-dimethylheptyl-Δ8-THC

  摘要：

  An enantioselective synthesis of the (1'S,2'R)-dimethylheptyl cannabinoid side chain has been developed and employed in the synthesis of 11-hydroxy-(1'S,2'R)-dimethylheptyl-Delta(8)-THC (3). Pharmacology, in vivo and in vitro, indicate (3) to be one of the most potent traditional cannabinoids known. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00385-0
• 作为产物：
  描述：

  5-[(2S,3R)-3-methyloctan-2-yl]benzene-1,3-diol 、 2,2-Dimethyl-propionic acid (1R,4R,5S)-4-hydroxy-6,6-dimethyl-bicyclo[3.1.1]hept-2-en-2-ylmethyl ester 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 2,2-Dimethyl-propionic acid (6aR,10aR)-3-((1S,2R)-1,2-dimethyl-heptyl)-1-hydroxy-6,6-dimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-9-ylmethyl ester
  参考文献：
  名称：

  Enantioselective synthesis and pharmacology of 11-hydroxy-(1'S,2'R)-dimethylheptyl-Δ8-THC

  摘要：

  An enantioselective synthesis of the (1'S,2'R)-dimethylheptyl cannabinoid side chain has been developed and employed in the synthesis of 11-hydroxy-(1'S,2'R)-dimethylheptyl-Delta(8)-THC (3). Pharmacology, in vivo and in vitro, indicate (3) to be one of the most potent traditional cannabinoids known. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00385-0

文献信息

• Enantioselective synthesis and pharmacology of 11-hydroxy-(1'S,2'R)-dimethylheptyl-Δ8-THC
  作者：John Liddle、John W. Huffman、Jenny L. Wiley、Billy R. Martin

  DOI：10.1016/s0960-894x(98)00385-0

  日期：1998.8

  An enantioselective synthesis of the (1'S,2'R)-dimethylheptyl cannabinoid side chain has been developed and employed in the synthesis of 11-hydroxy-(1'S,2'R)-dimethylheptyl-Delta(8)-THC (3). Pharmacology, in vivo and in vitro, indicate (3) to be one of the most potent traditional cannabinoids known. (C) 1998 Elsevier Science Ltd. All rights reserved.