4-(2,6-Dimethoxy-4-pentylphenyl)-6,6-dimethylbicyclo<3.1.1>hept-3-en-2-one | 132345-33-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: 4-(2,6-Dimethoxy-4-pentylphenyl)-6,6-dimethylbicyclo<3.1.1>hept-3-en-2-one
• CAS: 132345-33-6
• 化学式: C₂₂H₃₀O₃
• 分子量: 342.478
• InChiKey: ZMNOPMIPOUZPKQ-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-(2,6-Dimethoxy-4-pentylphenyl)-6,6-dimethylbicyclo<3.1.1>hept-3-en-2-one 在 丙烷-1-硫醇 、 sodium hydride 作用下， 生成 4-(2-Methoxy-4-pentyl-6-(methoxymethoxy)phenyl)-6,6-dimethylbicyclo<3.1.1>hept-3-en-2-one
  参考文献：
  名称：

  Synthesis of both enantiomers of nabilone from a common intermediate. Enantiodivergent synthesis of cannabinoids

  摘要：

  Both enantiomers of the synthetic cannabinoid nabilone (4) have been synthesized from a common intermediate, enone 7. Enone 7 was prepared by reaction of [2,6-dimethoxy-4-(1,1-dimethylheptyl)phenyl]lithium with (+)-apoverbenone (2), followed by PDC oxidation. Li/NH3 reduction of 7 gave saturated ketone 9, which, after ether cleavage to 10, afforded (6aS,10aR)-hexahydrodibenzopyran 15 on reaction with SnCl4. Isomerization to 6aR,10aR ketone 16 followed by ether cleavage gave the 6aR,10aR enantiomer of nabilone (4). The 6aS,10aS enantiomer of 4 (24) was prepared from 7 by ether cleavage to 18 and rearrangement to nonracemic tetrahydrodibenzopyran 20 using AlCl3. Dissolving metal reduction of 20 followed by ether cleavage gave the 6aS,10aS enantiomer of nabilone (24). A model sequence employing (2,6-dimethoxyphenyl)lithium at the first step was carried out and the structure of one of the intermediates, ketone 12, was established by X-ray crystallography. A new preparation of apoverbenone (2) has been developed.

  DOI：

  10.1021/jo00006a021

文献信息

• Stereoselective synthesis of the epimeric Δ7-tetrahydrocannabinols
  作者：John W. Huffman、W. Kenneth Banner、Grace K. Zoorob、H. Howard Joyner、Patricia H. Reggio、Billy R. Martin、David R. Compton

  DOI：10.1016/0040-4020(94)00995-7

  日期：1995.1

  Both C9 epimers of Δ7-THC (3 and 4) have been synthesized from Δ8-THC methyl ether (12). Hydroboration of 12 gave a mixture of stereoisomeric 8-hydroxyhexahydrocannabinols. The 8α-ol was converted into the 9β-methyl epimer (4) of Δ7-THC, while the 8β-ol was converted into 3. Molecular modeling indicated that 4 should have significant cannabinoid activity, while 3 was predicted to be weakly active.

  的两个差向异构体C9 Δ 7 -THC（3和4）已经被从合成Δ 8 -THC甲基醚（12）。12的氢硼化得到立体异构的8-羟基六氢大麻酚的混合物。所述8α醇转化成9β甲基差向异构体（4）的Δ 7 -THC，而8β醇转化成3。分子模型表明，4个具有明显的大麻素活性，而3个被预测为弱活性。这些预测被体外和体内药理学证实。