diethyl 2-[(1R,6R)-3-methyl-6-(1-prop-1-en-2-yl)-cyclohex-2-enyl]-5-pentylphenyl phosphate | 1415961-22-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: diethyl 2-[(1R,6R)-3-methyl-6-(1-prop-1-en-2-yl)-cyclohex-2-enyl]-5-pentylphenyl phosphate
• 英文别名: Diethyl 2-((1R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-enyl)-5-pentylphenyl phosphate；diethyl [2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylphenyl] phosphate
• CAS: 1415961-22-6
• 化学式: C₂₅H₃₉O₄P
• 分子量: 434.556
• InChiKey: IDTAEMIPNIXJOS-LADGPHEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 2-[(1R,6R)-3-methyl-6-(1-prop-1-en-2-yl)-cyclohex-2-enyl]-5-pentylphenyl phosphate 在 氨 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以82%的产率得到[(1R,6R)-3-methyl-6-(1-prop-1-en-2-yl)-cyclohex-2-enyl]-4-pentylbenzene
  参考文献：
  名称：

  Improved accessibility to the desoxy analogues of Δ9-tetrahydrocannabinol and cannabidiol

  摘要：

  Desoxy analogues of Delta(9)-tetrahydrocannabinol (THC) and cannabidiol (CBD) have been reported to provide a novel mode of analgesia whilst avoiding the psychotropic side effects associated with most cannabinoid drugs. A detailed and improved synthesis of desoxy THC, desoxy CBD and didesoxy CBD is reported here. The key improvements include a concentration-dependent boron trifluoride mediated electrophilic aromatic substitution which was used to synthesize both THC and CBD analogues. The synthetic route is general and could be applied to the development of a library of modified desoxy THC and desoxy CBD analogues. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.080
• 作为产物：
  描述：

  反式-薄荷基-2,8-二烯-1-醇 在 三氟化硼乙醚 、 sodium hydride 、 magnesium sulfate 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 3.0h， 生成 diethyl 2-[(1R,6R)-3-methyl-6-(1-prop-1-en-2-yl)-cyclohex-2-enyl]-5-pentylphenyl phosphate
  参考文献：
  名称：

  Improved accessibility to the desoxy analogues of Δ9-tetrahydrocannabinol and cannabidiol

  摘要：

  Desoxy analogues of Delta(9)-tetrahydrocannabinol (THC) and cannabidiol (CBD) have been reported to provide a novel mode of analgesia whilst avoiding the psychotropic side effects associated with most cannabinoid drugs. A detailed and improved synthesis of desoxy THC, desoxy CBD and didesoxy CBD is reported here. The key improvements include a concentration-dependent boron trifluoride mediated electrophilic aromatic substitution which was used to synthesize both THC and CBD analogues. The synthetic route is general and could be applied to the development of a library of modified desoxy THC and desoxy CBD analogues. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.080

文献信息

• Improved accessibility to the desoxy analogues of Δ9-tetrahydrocannabinol and cannabidiol
  作者：Shane M. Wilkinson、Jason Price、Michael Kassiou

  DOI：10.1016/j.tetlet.2012.10.080

  日期：2013.1

  Desoxy analogues of Delta(9)-tetrahydrocannabinol (THC) and cannabidiol (CBD) have been reported to provide a novel mode of analgesia whilst avoiding the psychotropic side effects associated with most cannabinoid drugs. A detailed and improved synthesis of desoxy THC, desoxy CBD and didesoxy CBD is reported here. The key improvements include a concentration-dependent boron trifluoride mediated electrophilic aromatic substitution which was used to synthesize both THC and CBD analogues. The synthetic route is general and could be applied to the development of a library of modified desoxy THC and desoxy CBD analogues. (C) 2012 Elsevier Ltd. All rights reserved.