3-(6-aminohexyl)-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol | 870789-88-1

• 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: 3-(6-aminohexyl)-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol
• 英文别名: (6aR,10aR)-3-(6-aminohexyl)-6,6,9-trimethyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
• CAS: 870789-88-1
• 化学式: C₂₂H₃₃NO₂
• 分子量: 343.51
• InChiKey: LOIWLGWSOIKYNP-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(6-aminohexyl)-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol 、 乙酸酐 在 吡啶 、 Polymer 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以20.1 mg的产率得到N-(6-(1-hydroxy-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-3-yl)hexyl)acetamide
  参考文献：
  名称：

  Δ⁹-Tetrahydrocannabinol Immunochemical Studies:  Haptens, Monoclonal Antibodies, and a Convenient Synthesis of Radiolabeled Δ⁹-Tetrahydrocannabinol

  摘要：

  Immunopharmacotherapy as an approach to combat drugs of abuse has become an active area of investigation. Marijuana is the most commonly used illicit drug in the U.S. The main active chemical in marijuana is Delta(9)-tetrahydrocannabinol (Delta(9)-THC); hence, monoclonal antibodies with high affinity and specificity for Delta(9)-tetrahydrocannabinol could be valuable immunopharmacotherapeutic intervention and diagnostic tools. We have synthesized immunoconjugates that induce an effective immune response to Delta(9)-THC and describe a convenient synthesis of radiolabeled Delta(9)-THC. We demonstrate the value and use of this probe to select anti-Delta(9)-THC antibodies that bind Delta(9)-THC with good affinity. The synthetic route to radiolabeled Delta(9)-THC has enabled the correct assessment of the affinity of these antibodies to their ligand and may facilitate future binding studies between Delta(9)-THC and its analogues and the cannabinoid receptors.

  DOI：

  10.1021/jm050442r
• 作为产物：
  描述：

  3,5-二甲氧基苯甲醛 在 palladium on activated charcoal sodium azide 、 三氟化硼乙醚 、 水 、 氢气 、 三溴化硼 、 magnesium sulfate 、 magnesium 、 溶剂黄146 、 三苯基膦 、 sodium iodide 、 Polymer 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.08h， 生成 3-(6-aminohexyl)-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol
  参考文献：
  名称：

  Δ⁹-Tetrahydrocannabinol Immunochemical Studies:  Haptens, Monoclonal Antibodies, and a Convenient Synthesis of Radiolabeled Δ⁹-Tetrahydrocannabinol

  摘要：

  Immunopharmacotherapy as an approach to combat drugs of abuse has become an active area of investigation. Marijuana is the most commonly used illicit drug in the U.S. The main active chemical in marijuana is Delta(9)-tetrahydrocannabinol (Delta(9)-THC); hence, monoclonal antibodies with high affinity and specificity for Delta(9)-tetrahydrocannabinol could be valuable immunopharmacotherapeutic intervention and diagnostic tools. We have synthesized immunoconjugates that induce an effective immune response to Delta(9)-THC and describe a convenient synthesis of radiolabeled Delta(9)-THC. We demonstrate the value and use of this probe to select anti-Delta(9)-THC antibodies that bind Delta(9)-THC with good affinity. The synthetic route to radiolabeled Delta(9)-THC has enabled the correct assessment of the affinity of these antibodies to their ligand and may facilitate future binding studies between Delta(9)-THC and its analogues and the cannabinoid receptors.

  DOI：

  10.1021/jm050442r

文献信息

• Δ⁹-Tetrahydrocannabinol Immunochemical Studies:  Haptens, Monoclonal Antibodies, and a Convenient Synthesis of Radiolabeled Δ⁹-Tetrahydrocannabinol
  作者：Longwu Qi、Noboru Yamamoto、Michael M. Meijler、Laurence J. Altobell、George F. Koob、Peter Wirsching、Kim D. Janda

  DOI：10.1021/jm050442r

  日期：2005.11.1

  Immunopharmacotherapy as an approach to combat drugs of abuse has become an active area of investigation. Marijuana is the most commonly used illicit drug in the U.S. The main active chemical in marijuana is Delta(9)-tetrahydrocannabinol (Delta(9)-THC); hence, monoclonal antibodies with high affinity and specificity for Delta(9)-tetrahydrocannabinol could be valuable immunopharmacotherapeutic intervention and diagnostic tools. We have synthesized immunoconjugates that induce an effective immune response to Delta(9)-THC and describe a convenient synthesis of radiolabeled Delta(9)-THC. We demonstrate the value and use of this probe to select anti-Delta(9)-THC antibodies that bind Delta(9)-THC with good affinity. The synthetic route to radiolabeled Delta(9)-THC has enabled the correct assessment of the affinity of these antibodies to their ligand and may facilitate future binding studies between Delta(9)-THC and its analogues and the cannabinoid receptors.