2-methyl-2-(3,5-dimethoxyphenyl)pentane | 180415-83-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methyl-2-(3,5-dimethoxyphenyl)pentane
• 英文别名: 1,3-dimethoxy-5-(2-methylpentan-2-yl)benzene；1-(1,1-dimethyl-butyl)-3,5-dimethoxy-benzene；1-(1,1-Dimethyl-butyl)-3,5-dimethoxy-benzol
• CAS: 180415-83-2
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: OYCFCIKAZRDEMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  2-methyl-2-(3,5-dimethoxyphenyl)pentane 在 乙醚 、 三氟化硼 、 三溴化硼 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 Adamantane-1-carboxylic acid (6aS,10aS)-3-(1,1-dimethyl-butyl)-1-hydroxy-6,6-dimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-9-ylmethyl ester
  参考文献：
  名称：

  Neuroprotective (+) 3S, 4S cannabinoids with modified 5′-side chain

  摘要：

  The synthesis and evaluation of two novel cannabinoids belonging to the (+) 3S, 4S nonpsychotropic series are described These derivatives bind to the NMDA receptor but have lower affinities than dexanabinol (HU-211), the series benchmark. The novel compounds protect neurons against NMDA-induced toxicity in cortical cell cultures and have lower toxicity to host neurons than dexanabinol. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00272-7
• 作为产物：
  描述：

  Phosphoric acid 4-(1,1-dimethyl-butyl)-2,6-dimethoxy-phenyl ester diethyl ester 在 氨 、 lithium 作用下， 生成 2-methyl-2-(3,5-dimethoxyphenyl)pentane
  参考文献：
  名称：

  Neuroprotective (+) 3S, 4S cannabinoids with modified 5′-side chain

  摘要：

  The synthesis and evaluation of two novel cannabinoids belonging to the (+) 3S, 4S nonpsychotropic series are described These derivatives bind to the NMDA receptor but have lower affinities than dexanabinol (HU-211), the series benchmark. The novel compounds protect neurons against NMDA-induced toxicity in cortical cell cultures and have lower toxicity to host neurons than dexanabinol. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00272-7

文献信息

• Resorcinol Derivatives: A Novel Template for the Development of Cannabinoid CB₁/CB₂ and CB₂-Selective Agonists
  作者：Jenny L. Wiley、Irina D. Beletskaya、Edward W. Ng、Zongmin Dai、Peter J. Crocker、Anu Mahadevan、Raj K. Razdan、Billy R. Martin

  DOI：10.1124/jpet.301.2.679

  日期：2002.5.1

  these analogs revealed several structural features that were important for maintaining CB(1) receptor recognition and in vivo activity, including the presence of a branched lipophilic side chain and free phenols as well as substitution of a cyclohexane as the second ring of these bicyclic cannabinoids. Many of these analogs exhibited CB(2) selectivity, particularly the dimethoxyresorcinol analogs, and

  尚不十分了解Delta（9）-四氢大麻酚的苯并吡喃取代基的氧在定义对脑大麻素（CB（1））受体的亲和力中的作用；然而，众所周知，打开吡喃环会导致效力和亲和力的提高，如CP 55940 [[-）-顺-3- [2-羟基-4（1,1-二甲基庚基）苯基]-反式-4-（3-羟基-丙基）环己醇]或在非活性大麻素中（如大麻二酚）。在本研究中，合成了一系列类似于大麻二酚的双环间苯二酚，并在体外和体内进行了测试。对这些类似物的结构-活性关系的分析显示了几个结构特征，这些特征对于维持CB（1）受体的识别和体内活性非常重要，包括存在分支的亲脂性侧链和游离酚，以及取代环己烷作为这些双环大麻素的第二个环。这些类似物中的许多表现出CB（2）选择性，特别是二甲氧基间苯二酚类似物，并且更长的侧链长度增强了这种选择性。因此，与大麻二酚不同，这些间苯二酚衍生物具有对CB（1）和/或CB（2）受体的良好亲和力以及强大的体内活性
• 2-CYCLOALKYL RESORCINOL CANNABINERGIC LIGANDS
  申请人：NORTHEASTERN UNIVERSITY

  公开号：US20150274623A1

  公开（公告）日：2015-10-01

  The present invention relates to novel 2-cycloalkyl resorcinol compounds; to pharmaceutical compositions comprising the compounds; and to methods of preparing the compounds and uses thereof. The disclosed compounds can bind to and modulate the cannabinoid receptors and thus, they are specific ligands for these receptors. 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.

  本发明涉及一种新型的2-环烷基邻苯二酚化合物；涉及含有该化合物的药物组合物；以及制备该化合物和使用该化合物的方法。所披露的化合物能够结合和调节大麻素受体，因此它们是这些受体的特异性配体。当以治疗有效量的方式给予这些发明化合物给个体或动物时，会在个体或动物中产生足够高的该化合物水平以引起生理反应。这种生理反应可能有助于治疗许多生理状况。
• Methods of treating or preventing autoimmune diseases with 2,4-pyrimidinediamine compounds
  申请人：RIGEL PHARMACEUTICALS, INC.

  公开号：US10259826B2

  公开（公告）日：2019-04-16

  The present invention provides methods of treating or preventing autoimmune diseases with 2,4-pyrimidinediamine compounds, as well as methods of treating, preventing or ameliorating symptoms associated with such diseases. Specific examples of autoimmune diseases that can be treated or prevented with the compounds include rheumatoid arthritis and/or its associated symptoms, systemic lupus erythematosis and/or its associated symptoms and multiple sclerosis and/or its associated symptoms.

  本发明提供了用2,4-嘧啶二胺化合物治疗或预防自身免疫性疾病的方法，以及治疗、预防或改善与此类疾病相关症状的方法。可使用本发明化合物治疗或预防的自身免疫性疾病的具体实例包括类风湿性关节炎和/或其相关症状、系统性红斑狼疮和/或其相关症状以及多发性硬化症和/或其相关症状。
• Structure–activity relationships for 1′,1′-dimethylalkyl-Δ 8 -tetrahydrocannabinols
  作者：John W Huffman、John R.A Miller、John Liddle、Shu Yu、Brian F Thomas、Jenny L Wiley、Billy R Martin

  DOI：10.1016/s0968-0896(02)00649-1

  日期：2003.4

  A series of 1',1'-dimethylalkyl-Delta(8)-tetrahydrocannabinol analogues with C-3 side chains of 2-12 carbon atoms has been synthesized and their in vitro and in vivo pharmacology has been evaluated. The lowest member of the series, 1',1'-dimethylethyl-Delta(8)-THC (8, n = 0) has good affinity for the CB1 receptor, but is inactive in vivo. The dimethylpropyl (8, n = 1) through dimethyldecyl (8, n = 8) all have high affinity for the CB1 receptor and are full agonists in vivo. 1',1'-Dimethylundecyl-Delta(8)-THC (8, n = 9) has significant affinity for the receptor (K-i = 25.8 +/- 5.8 nM), but has reduced potency in vivo. The dodecyl analogue (8, n = 10) has little affinity for the CB1 receptor and is inactive in vivo. A quantitative structure-activity relationship study of the side chain region of these compounds is consistent with the concept that for optimum affinity and potency the side chain must be of a length which will permit its terminus to loop back in proximity to the phenolic ring of the cannabinoid. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Tetrahydrocannabinol Homologs. XVII.¹
  作者：Roger Adams、Ben F. Aycock、S. Loewe

  DOI：10.1021/ja01182a067

  日期：1948.2