5-(3,5-二甲氧基苯基)戊酸乙酯 | 197178-54-4

• 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: 5-(3,5-二甲氧基苯基)戊酸乙酯
• 英文名称: 5-(3,5-dimethoxyphenyl)pentanoic acid ethyl ester
• 英文别名: ethyl 5-(3,5-dimethoxyphenyl)pentanoate；Ethyl 5-(3,5-dimethoxyphenyl)pentanoate
• CAS: 197178-54-4
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: NYVRUSPOKCTJSA-UHFFFAOYSA-N

物化性质

• 沸点：
  371.6±32.0 °C(Predicted)
• 密度：
  1.039±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(3,5-二甲氧基苯基)戊酸乙酯 在 lithium aluminium tetrahydride 、 四溴化碳 、 三氟化硼乙醚 、 三溴化硼 、 magnesium sulfate 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 26.92h， 生成 四氢大麻酚
  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：

  5-(3,5-dimethoxyphenyl)penta-2,4-dienoic acid ethyl ester 在 palladium dihydroxide 、 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 16.5h， 以85%的产率得到5-(3,5-二甲氧基苯基)戊酸乙酯
  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

• ANGIOGENIC RESORCINOL DERIVATIVES
  申请人：Makriyannis Alexandros

  公开号：US20120172339A1

  公开（公告）日：2012-07-05

  Novel resorcinol derivatives and methods of preparation and use are presented. These compounds can stimulate angiogenesis as a biological function triggered by the activation of one cannabinoid receptor distinct from CB1 and CB2. Thus, these compounds are specific ligands for one cannabinoid receptor distinct from CB1 and CB2. The invented compounds, when administered in a therapeutically effective amount to an individual or animal, results in a sufficiently high level of that compound in the individual or animal to cause a physiological response. The physiological response may be useful to treat a number of physiological conditions.

  本发明提供了新型间苯二酚衍生物的制备方法和用途。这些化合物可以刺激血管生成，作为一种由激活与CB1和CB2不同的一种大麻素受体而触发的生物学功能。因此，这些化合物是与CB1和CB2不同的一种大麻素受体的特异性配体。当以治疗有效量的方式向个体或动物施用这些发明化合物时，会在个体或动物中产生足够高的该化合物水平，从而引起生理反应。这种生理反应可能有助于治疗许多生理状况。
• 一种大麻二酚半抗原与完全抗原的制备方法及应用
  申请人：郑州左安检测科技有限公司

  公开号：CN115160135B

  公开（公告）日：2023-11-03

  一种大麻二酚半抗原与完全抗原的制备方法及应用，大麻二酚半抗原是由3,5‑二甲氧基苯甲醛与三乙基‑4‑磷化物反应生成（2E，4E）‑5‑（3,5‑二甲氧基苯基）‑2,4‑戊二烯酸乙酯，随后经PdC/H2还原，HBr/HoAc脱甲基和皂化反应得到5‑（3,5‑二羟苯基）戊酸，最后再与(1S,4R)‑1‑甲基‑4‑(1‑甲基乙烯基)‑2‑环己烯‑1‑醇反应得到大麻二酚半抗原；大麻二酚完全抗原由大麻二酚半抗原与载体蛋白偶联得到。本发明制备的抗原呈现出特异性的大麻二酚抗原决定簇，使得筛选出高特异性的大麻二酚单克隆抗体成为可能。产生的抗体特异性高、灵敏度高，对大麻及其衍生物均无明显的交叉反应，可用于建立酶联免疫分析方法和胶体金、荧光快速检测试纸法，实现对样品中大麻二酚的快速检测。
• Discovery of KLS-13019, a Cannabidiol-Derived Neuroprotective Agent, with Improved Potency, Safety, and Permeability
  作者：William A. Kinney、Mark E. McDonnell、Hua Marlon Zhong、Chaomin Liu、Lanyi Yang、Wei Ling、Tao Qian、Yu Chen、Zhijie Cai、Dean Petkanas、Douglas E. Brenneman

  DOI：10.1021/acsmedchemlett.6b00009

  日期：2016.4.14

  Cannabidiol is the nonpsychoactive natural component of C. sativa that has been shown to be neuroprotective in multiple animal models. Our interest is to advance a therapeutic candidate for the orphan indication hepatic encephalopathy (HE). HE is a serious neurological disorder that occurs in patients with cirrhosis or liver failure. Although cannabidiol is effective in models of HE, it has limitations in terms of safety and oral bioavailability. Herein, we describe a series of side chain modified resorcinols that were designed for greater hydrophilicity and "drug likeness", while varying hydrogen bond donors, acceptors, architecture, basicity, neutrality, acidity, and polar surface area within the pendent group. Our primary screen evaluated the ability of the test agents to prevent damage to hippocampal neurons induced by ammonium acetate and ethanol at clinically relevant concentrations. Notably, KLS-13019 was 50-fold more potent and >400-fold safer than cannabidiol and exhibited an in vitro profile consistent with improved oral bioavailability.
• Synthesis of 5′,11-dihydroxy-Δ8-tetrahydrocannabinol
  作者：John W. Huffman、Ming-Jung Wu、W.Kenneth Banner、Dong Dai

  DOI：10.1016/s0040-4020(97)00868-5

  日期：1997.9

  The synthesis of a polar cannabinoid, 5',11-dihydroxy-Delta(8)-tetrahydrocannabinol (2), has been carried out. A key step in the synthesis is the reaction of an aryllithium derived from 1-(tert-butyldimethylsilyloxy)-5-(3, 5-dimethoxyphenyl)pentane with apoverbenone. Subsequent conversions provided diol 2, which has significantly less affinity for the cannabinoid receptor than Delta(8)-THC. (C) 1997 Elsevier Science Ltd.
• [EN] ANGIOGENIC RESORCINOL DERIVATIVES<br/>[FR] DÉRIVÉS DU RÉSORCINOL ANGIOGÉNIQUES
  申请人：UNIV NORTHEASTERN

  公开号：WO2011006099A1

  公开（公告）日：2011-01-13

  Novel resorcinol derivatives and methods of preparation and use are presented. These compounds can stimulate angiogenesis as a biological function triggered by the activation of one cannabinoid receptor distinct from CB1 and CB2. Thus, these compounds are specific ligands for one cannabinoid receptor distinct from CB1 and CB2. The invented compounds, when administered in a therapeutically effective amount to an individual or animal, results in a sufficiently high level of that compound in the individual or animal to cause a physiological response. The physiological response may be useful to treat a number of physiological conditions.