(6aR,10aR)-3-(1',1'-dimethylheptyl)-Δ⁸-tetrahydrocannabinol 1-O-acetate | 61597-29-3

• 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,10aR)-3-(1',1'-dimethylheptyl)-Δ⁸-tetrahydrocannabinol 1-O-acetate
• 英文别名: [(6aR,10aR)-6,6,9-trimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-yl] acetate
• CAS: 61597-29-3
• 化学式: C₂₇H₄₀O₃
• 分子量: 412.613
• InChiKey: KCCCXNIOWSNFBC-FGZHOGPDSA-N

物化性质

• 沸点：
  473.7±45.0 °C(Predicted)
• 密度：
  0.992±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6aR,10aR)-3-(1',1'-dimethylheptyl)-Δ⁸-tetrahydrocannabinol 1-O-acetate 在 selenium(IV) oxide 、 双氧水 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 49.5h， 以20%的产率得到(6aR,10aR)-1-羟基-6,6-二甲基-3-(2-甲基辛-2-基)-6a,7,10,10a-四氢苯并[c]色原烯-9-羧酸
  参考文献：
  名称：

  [EN] METHODS AND COMPOSITIONS RELATING TO ULTRAPURE 5-(1,1-DIMETHYLHEPTYL)-RESORCINOL
  [FR] PROCÉDÉS ET COMPOSITIONS RELATIFS AU 5-(1,1-DIMÉTHYLHEPTYL)-RÉSORCINOL ULTRAPUR

  摘要：

  公开号：

  WO2019079677A8
• 作为产物：
  描述：

  5-(1,1-二甲基庚基)间苯二酚 在 吡啶 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 (6aR,10aR)-3-(1',1'-dimethylheptyl)-Δ⁸-tetrahydrocannabinol 1-O-acetate
  参考文献：
  名称：

  大麻素代谢物的合成：Ajulemic Acid 和 胡-210

  摘要：

  据报道，大麻素代谢物比其母体化合物更有效。其中，ajulemic acid （AJA） 是 Δ9-THC-11-oic acid 的侧链类似物，这将是发现更有效类似物的良好模板结构。在此，我们优化了关键的烯丙基氧化步骤，以高产率引入 C-11 羟基。在此条件下制备了一系列化合物，包括 胡-210、11-nor-Δ8-四氢大麻酚 （THC）-羧酸和 Δ9-THC-羧酸。

  DOI：

  10.3390/molecules29020526

文献信息

• Novel Cannabinol Probes for CB1 and CB2 Cannabinoid Receptors
  作者：Anu Mahadevan、Craig Siegel、Billy R. Martin、Mary E. Abood、Irina Beletskaya、Raj K. Razdan

  DOI：10.1021/jm0001572

  日期：2000.10.1

  CBN-3-(1',1'-dimethylheptyl) analogues were prepared by sulfur dehydrogenation of Delta(8)-THC-3-(1',1'-dimethylheptyl) analogues. 9-Substituted CBN analogues were prepared by the standard sulfur dehydrogenation of 9-substituted Delta(8)-THC analogues (Scheme 1), which in turn were prepared following our previous procedure using selenium dioxide oxidation of the corresponding Delta(8)-THCs followed by sodium

  THCs的酚羟基对于与CB1受体结合很重要，但对与CB2受体结合却不那么重要的发现促使我们将这一发现扩展到大麻酚（CBN）系列。为了研究CBN类似物的SAR，选择了在C-1，C-3和C-9位置具有取代基的CBN衍生物，因为这些位置在THC的SAR中起着关键作用。CBN-3-（1'，1'-二甲基庚基）类似物是通过Delta（8）-THC-3-（1'，1'-二甲基庚基）类似物的硫脱氢制备的。通过9-取代的Delta（8）-THC类似物的标准硫脱氢反应制备9-取代的CBN类似物（方案1），依次按照我们先前的步骤进行制备，使用相应的Delta（8）-THC的二氧化硒氧化，再用亚氯酸钠氧化，得到9-羧基-Delta（8）-THC衍生物。通过用LiAlH（4）还原从相应的9-羰甲氧基-CBN类似物制备11-羟基-CBN类似物。脱氧-CBN类似物14由相应的Delta（8）-THC类似物11制备，方法是
• Ultrapure ajulemic acid has improved CB2 selectivity with reduced CB1 activity
  作者：Mark A. Tepper、Robert B. Zurier、Sumner H. Burstein

  DOI：10.1016/j.bmc.2014.04.062

  日期：2014.7

  Ajulemic acid, a side-chain analog of Delta(8)-THC-11-oic acid, was designed as a potent therapeutic agent free of the psychotropic adverse effects typical of most cannabinoids. Subsequent studies of ajulemic acid have yielded widely divergent findings on the occurrence of these adverse effects. To help resolve these discrepancies, we have prepared highly purified ajulemic acid using a different synthetic method than previously reported in the literature and compared its cannabinoid receptor binding constants with those obtained using several other preparations from different sources. Whereas CB2 binding did not vary greatly among all of the samples, the CB1 binding showed a wide range of affinities. The highly purified product (JBT-101) reported here had the weakest affinity for CB1 while the original preparation (HU-239) showed the strongest affinity for CBI. The CB1/CB2 ratio of affinities was 12.3 for JBT-101 whereas that for HU-239 was 0.19, a 65-fold difference. Functional responses such as catalepsy and hypothermia using JBT-101 versus HU-239 displayed reduced CB1 activity in keeping with the receptor binding data. Thus, earlier conclusions on the limited therapeutic index for ajulemic acid need to be reconsidered in the light of the data now obtained using JBT-101. (C) 2014 Elsevier Ltd. All rights reserved.
• [EN] ULTRAPURE TETRAHYDROCANNABINOL-11-OIC ACIDS<br/>[FR] ACIDES TÉTRAHYDROCANNABINOL-11-OÏQUES ULTRAPURS
  申请人：CORBUS PHARMACEUTICALS INC

  公开号：WO2014127016A3

  公开（公告）日：2015-11-26
• Small molecule immunopotentiators and assays for their detection
  申请人：Valiante Nicholas

  公开号：US20110104186A1

  公开（公告）日：2011-05-05

  The invention provides immunostimulatory compositions comprising a small molecule immuno-potentiator (SMIP) compound and methods of administration thereof. Also provided are methods of administering a SMIP compound in an effective amount to enhance the immune response of a subject to an antigen. Further provided are novel compositions and methods of administering SMIP compounds alone or in combination with another agent for the treatment of cancer, infectious diseases and/or allergies/asthma. In a further aspect, the invention relates generally to methods of screening for small molecule immuno-modulatory compositions.
• [EN] METHODS AND COMPOSITIONS RELATING TO ULTRAPURE 5-(1,1-DIMETHYLHEPTYL)-RESORCINOL<br/>[FR] PROCÉDÉS ET COMPOSITIONS RELATIFS AU 5-(1,1-DIMÉTHYLHEPTYL)-RÉSORCINOL ULTRAPUR
  申请人：CORBUS PHARMACEUTICALS INC

  公开号：WO2019079677A8

  公开（公告）日：2019-05-31