3,5-二甲氧基-1-(1-庚烯基)苯 | 23815-39-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,5-二甲氧基-1-(1-庚烯基)苯
• 英文名称: 3,5-dimethoxy-1-(1-heptenyl)benzene
• 英文别名: 1,5-dimethoxy-5-(heptyl-1-en-1-yl)benzene；1-(1-Hepten-1-yl)-3,5-dimethoxybenzene；1-hept-1-enyl-3,5-dimethoxybenzene
• CAS: 23815-39-6
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: QNYLZIJLUKWEGD-UHFFFAOYSA-N

物化性质

• 沸点：
  343.4±22.0 °C(Predicted)
• 密度：
  0.958±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,5-二甲氧基-1-(1-庚烯基)苯 在 palladium on activated charcoal 氢气 、 三溴化硼 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 生成 (1'R,2'R)-4-heptyl-5'-methyl-2'-(prop-1-en-2-yl)-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-2,6-diol
  参考文献：
  名称：

  C1‘-Cycloalkyl Side Chain Pharmacophore in Tetrahydrocannabinols

  摘要：

  In earlier work we have provided evidence for the presence of a subsite within the CB1 and CB2 cannabinoid receptor binding domains of classical cannabinoids. This putative subsite corresponds to substituents on the C1'-position of the C3-alkyl side chain, a key pharmacophoric feature in this class of compounds. We have now refined this work through the synthesis of additional C1'-cycloalkyl compounds using newly developed approaches. Our findings indicate that the C1'-cyclopropyl and C1'-cyclopentyl groups are optimal pharmacophores for both receptors while the C1'-cyclobutyl group interacts optimally with CB1 but not with CB2. The C1'-cyclohexyl analogs have reduced affinities for both CB1 and CB2. However, these affinities are significantly improved with the introduction of a C2'-C3' cis double bond that modifies the available conformational space within the side chain and allows for a better accommodation of a six-membered ring within the side chain subsite. Our SAR results are highlighted by molecular modeling of key analogs.

  DOI：

  10.1021/jm070121a
• 作为产物：
  描述：

  1-己硫醇 在 sodium hydride 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 3,5-二甲氧基-1-(1-庚烯基)苯
  参考文献：
  名称：

  4-硝基苯砜的合成及在改性朱莉娅烯烃中的应用

  摘要：

  4-硝基苯基 (NP) 砜成功地用于与羰基化合物的改性 Julia 烯化反应。烯化反应通过羟醛加成、Smiles 重排和消除的顺序进行。砜很容易制备。从廉价的 com 开始，以两步顺序高产。可通过亲核芳族获得对氟硝基苯。被硫醇取代，随后被氧化。在标准下。使适应。NP 砜与多种芳烃之间的改良 Julia 反应。醛提供相应的苯乙烯、芪和肉桂酸酯衍生物。产率 ?97% 和良好的立体选择性。提出了机械原理来解释 obsd。结果。[在 SciFinder (R) 上]

  DOI：

  10.1055/s-2006-939682

文献信息

• Using (+)-carvone to access novel derivatives of (+)-ent-cannabidiol: The first asymmetric syntheses of (+)-ent-CBDP and (+)-ent-CBDV
  作者：Alexandra E. Golliher、Antonio J. Tenorio、Nina O. Dimauro、Nicolas R. Mairata、F. Omar Holguin、William Maio

  DOI：10.1016/j.tetlet.2021.152891

  日期：2021.3

  has a higher affinity to CB1/CB2 receptors than the natural stereoisomer. We have developed an inexpensive, stereoselective route to access ent-CBD derivatives using (+)-carvone as a starting material. In addition to (+)-CBD, we report the first syntheses of (+)-cannabidivarin, (+)-cannabidiphorol as well as C-6/C-8 homologues.

  (−)-大麻二酚 [(−)-CBD] 最近作为治疗神经炎症和其他神经退行性疾病的药物而受到重视；人们对其合成对映体 (+)-CBD 也产生了兴趣，它比天然立体异构体对 CB1/CB2 受体具有更高的亲和力。我们开发了一种廉价的立体选择性途径，使用 (+)-香芹酮作为起始材料来获取ent -CBD 衍生物。除了 (+)-CBD 之外，我们还首次合成了 (+)-cannabidivarin、(+)-cannabidiphorol 以及 C-6/C-8 同系物。
• Efficient Synthesis for Altering Side Chain Length on Cannabinoid Molecules and Their Effects in Chemotherapy and Chemotherapeutic Induced Neuropathic Pain
  作者：Wesley M. Raup-Konsavage、Diana E. Sepulveda、Daniel P. Morris、Shantu Amin、Kent E. Vrana、Nicholas M. Graziane、Dhimant Desai

  DOI：10.3390/biom12121869

  日期：——

  molecules would be based upon cannabigerol (CBG). Because CBG, and its side chain variants, are rapidly converted to other cannabinoids in the plant, there are typically only small amounts in plant extracts, thus prohibiting investigations related to CBG and CBG variant therapeutic effects. (2) Methods: To overcome this, we developed an efficient synthesis of corresponding resorcinol fragments using the

  (1) 背景：最近，在大麻中发现了一些四氢大麻酚和大麻二酚的侧链长度变体；然而，这些分子的前体将基于大麻酚 (CBG)。由于 CBG 及其侧链变体在植物中迅速转化为其他大麻素，因此植物提取物中通常只有少量大麻素，因此禁止与 CBG 和 CBG 变体治疗效果相关的研究。(2) 方法：为了克服这个问题，我们开发了一种使用 Wittig 反应有效合成相应间苯二酚片段的方法，该反应在酸催化下与香叶醇偶联，产生所需的 CBG 侧链变体。然后在化疗引起的神经性疼痛和降低结直肠癌细胞活力的动物模型中测试这些化合物。(3) 结果：我们发现所有侧链变体在剂量为 10 mg/kg 时同样能够减轻小鼠的神经性疼痛。然而，具有较短侧链的分子（即 CBGV 和 CBGB）更能降低结直肠癌细胞的活力。(4) 结论：本文开发的新合成方法将对大麻素、大麻酚、大麻素等其他小类大麻素侧链衍生物的研究具有实用价值。
• Novel insights into the antibacterial activities of cannabinoid biosynthetic intermediate, olivetolic acid, and its alkyl-chain derivatives
  作者：Yuan-E Lee、Takeshi Kodama、Hiroyuki Morita

  DOI：10.1007/s11418-022-01672-9

  日期：2023.3

  revealed that the incorporation of longer alkyl chains to the C-6 position in resorcylic acid conferred antibacterial properties against Staphylococcus aureus and Bacillus subtilis. The resultant olivetolic acid (OA) derivatives with n-undecyl and n-tridecyl side-chains, even those lacking the hydrophobic geranyl moiety from their C-3 positions, exhibited strong antibacterial activities against B. subtilis

  抗菌活性研究表明，在间苯二酚酸的 C-6 位上掺入较长的烷基链赋予了对金黄色葡萄球菌和枯草芽孢杆菌的抗菌特性。所得具有正十一烷基和正十三烷基侧链的橄榄酸 (OA) 衍生物，即使是那些在 C-3 位上缺乏疏水性香叶基部分的衍生物，也对枯草芽孢杆菌表现出很强的抗菌活性，MIC 值为 2.5 μM。此外，研究表明，大麻二酚酸（CBGA）的C-6位正庚基烷基链修饰有效增强了对枯草芽孢杆菌的活性，证明了烷基侧链在调节生物活性中的重要性。总体而言，本研究的结果为进一步评估 OA 和 CBGA 衍生物的抗菌活性以及其他各种生物活性提供了见解，特别是在核心骨架的烷基和异戊二烯基侧链位置优化了疏水性。新药物种子的发现。
• Synthesis of 4-Nitrophenyl Sulfones and Application in the Modified Julia Olefination
  作者：Jieping Zhu、Daniela Mirk、Jean-Marie Grassot

  DOI：10.1055/s-2006-939682

  日期：——

  4-Nitrophenyl (NP) sulfones were successfully employed in the modified Julia olefination reaction with carbonyl compds. The olefination reaction proceeds through a sequence of aldol addn., Smiles rearrangement, and elimination. The sulfones are easily prepd. in high yields in a two-step sequence starting from inexpensive com. available para-fluoronitrobenzenes via nucleophilic arom. substitution by

  4-硝基苯基 (NP) 砜成功地用于与羰基化合物的改性 Julia 烯化反应。烯化反应通过羟醛加成、Smiles 重排和消除的顺序进行。砜很容易制备。从廉价的 com 开始，以两步顺序高产。可通过亲核芳族获得对氟硝基苯。被硫醇取代，随后被氧化。在标准下。使适应。NP 砜与多种芳烃之间的改良 Julia 反应。醛提供相应的苯乙烯、芪和肉桂酸酯衍生物。产率 ?97% 和良好的立体选择性。提出了机械原理来解释 obsd。结果。[在 SciFinder (R) 上]
• C1‘-Cycloalkyl Side Chain Pharmacophore in Tetrahydrocannabinols
  作者：Demetris P. Papahatjis、Victoria R. Nahmias、Spyros P. Nikas、Thanos Andreou、Shakiru O. Alapafuja、Andrew Tsotinis、Jianxin Guo、Pusheng Fan、Alexandros Makriyannis

  DOI：10.1021/jm070121a

  日期：2007.8.1

  In earlier work we have provided evidence for the presence of a subsite within the CB1 and CB2 cannabinoid receptor binding domains of classical cannabinoids. This putative subsite corresponds to substituents on the C1'-position of the C3-alkyl side chain, a key pharmacophoric feature in this class of compounds. We have now refined this work through the synthesis of additional C1'-cycloalkyl compounds using newly developed approaches. Our findings indicate that the C1'-cyclopropyl and C1'-cyclopentyl groups are optimal pharmacophores for both receptors while the C1'-cyclobutyl group interacts optimally with CB1 but not with CB2. The C1'-cyclohexyl analogs have reduced affinities for both CB1 and CB2. However, these affinities are significantly improved with the introduction of a C2'-C3' cis double bond that modifies the available conformational space within the side chain and allows for a better accommodation of a six-membered ring within the side chain subsite. Our SAR results are highlighted by molecular modeling of key analogs.