(6aR,9R,10aR)-9-Chloro-6,6,9-trimethyl-3-pentyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol | 121694-20-0

• 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,9R,10aR)-9-Chloro-6,6,9-trimethyl-3-pentyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol
• 英文别名: (6aR,9R,10aR)-9-chloro-6,6,9-trimethyl-3-pentyl-7,8,10,10a-tetrahydro-6aH-benzo[c]chromen-1-ol
• CAS: 121694-20-0
• 化学式: C₂₁H₃₁ClO₂
• 分子量: 350.929
• InChiKey: WEACMXUFWZVIQH-WHSLLNHNSA-N

物化性质

• 沸点：
  421.6±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (6aR,9R,10aR)-9-Chloro-6,6,9-trimethyl-3-pentyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol 在 potassium 2-methylbutan-2-olate 作用下， 以 苯 为溶剂， 反应 0.5h， 生成 四氢大麻酚
  参考文献：
  名称：

  Addition and elimination of HCl to tetrahydrocannabinol isomers. A method for the preparation of stereospecifically 2H-labeled cannabinoids

  摘要：

  Addition of HCl gas to (-)Delta(8)-, (-)Delta(9)-, or (-)Delta(9,11)-THC solutions at -60 degrees C results in the formation of 9 alpha- and 9 beta-chlorohexahydrocannabinol (Cl-HHC). The addition appears to involve initial protonation of the double bond in the form of a bridged hydrogen cation followed by attack of the chloride anion at the most substituted 9-position. For both steps in the addition reaction the stereochemistry is dependent on the double bond position in the THC isomer. Elimination of HCl from each of the two addition products using potassium-tert-amylate leads exclusively to Delta(9)-THC in the case of 9 beta-Cl-HHC and to Delta(9,11)-THC in the case of 9 alpha-Cl-HHC. The individual addition products can be separated and used to obtain regio-and stereochemically H-2-isotopically labeled tetrahydrocannabinols which can be used in biophysical and biochemical studies.

  DOI：

  10.1002/(sici)1099-1344(199802)41:2<121::aid-jlcr55>3.0.co;2-s
• 作为产物：
  描述：

  四氢大麻酚 在 盐酸 、 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 生成 (6aR,9R,10aR)-9-Chloro-6,6,9-trimethyl-3-pentyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol
  参考文献：
  名称：

  Addition and elimination of HCl to tetrahydrocannabinol isomers. A method for the preparation of stereospecifically 2H-labeled cannabinoids

  摘要：

  Addition of HCl gas to (-)Delta(8)-, (-)Delta(9)-, or (-)Delta(9,11)-THC solutions at -60 degrees C results in the formation of 9 alpha- and 9 beta-chlorohexahydrocannabinol (Cl-HHC). The addition appears to involve initial protonation of the double bond in the form of a bridged hydrogen cation followed by attack of the chloride anion at the most substituted 9-position. For both steps in the addition reaction the stereochemistry is dependent on the double bond position in the THC isomer. Elimination of HCl from each of the two addition products using potassium-tert-amylate leads exclusively to Delta(9)-THC in the case of 9 beta-Cl-HHC and to Delta(9,11)-THC in the case of 9 alpha-Cl-HHC. The individual addition products can be separated and used to obtain regio-and stereochemically H-2-isotopically labeled tetrahydrocannabinols which can be used in biophysical and biochemical studies.

  DOI：

  10.1002/(sici)1099-1344(199802)41:2<121::aid-jlcr55>3.0.co;2-s

文献信息

• Novel synthesis of (−)-<i>trans</i>-Δ^9,11-tetrahydrocannabinol
  作者：Ali R. Banijamali、Alexandros Makriyannis

  DOI：10.1002/jhet.5570250324

  日期：1988.5

  Addition of hydrogen chloride gas to a solution of Δ8-tetrahydrocannabinol in dry dichloromethane at -60° in the presence of zinc chloride results in the formation of a higher concentration of 9-α-chlorohexa-hydrocannabinol (75%) than the thermodynamically more stable 9-β-chlorohexahydrocannabinol (25%). The two isomers can be separated by reverse-phase hplc. Elimination of hydrogen chloride from

  氯化氢气体的除了Δ的溶液8四氢大麻酚的无水二氯甲烷在-60℃在氯化锌的结果在9-α-chlorohexa-hydrocannabinol（75％）的高浓度的形成的存在比热力学上更稳定的9-β-氯六氢大麻酚（25％）。两种异构体可通过反相hplc分离。使用钾9-α-chlorohexa-hydrocannabinol氯化氢消除吨-amylate无水的条件下给出专门Δ 9,11中的65％总产率四氢大麻酚。
• BANIJAMALI, ALI R.;MAKRIYANNIS, ALEXANDROS, J. HETEROCYCL. CHEM., 25,(1988) N 3, C. 823-825
  作者：BANIJAMALI, ALI R.、MAKRIYANNIS, ALEXANDROS

  DOI：——

  日期：——