5-(2-butyl-[1,3]dithiolan-2-yl)-benzene-1,3-diol | 330855-39-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-(2-butyl-[1,3]dithiolan-2-yl)-benzene-1,3-diol
• 英文别名: 5-(2-butyl-1,3-dithiolan-2-yl)benzene-1,3-diol
• CAS: 330855-39-5
• 化学式: C₁₃H₁₈O₂S₂
• 分子量: 270.417
• InChiKey: OKLFWDQDVNWBGW-UHFFFAOYSA-N

物化性质

• 沸点：
  444.9±45.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  91.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-p-menth-2-ene-1,8-diol 、 5-(2-butyl-[1,3]dithiolan-2-yl)-benzene-1,3-diol 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 4.0h， 以26.3%的产率得到3-(2-butyl-[1,3]dithiolan-2-yl)-6,6,9-trimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-ol
  参考文献：
  名称：

  Synthesis and testing of novel classical cannabinoids: exploring the side chain ligand binding pocket of the CB1 and CB2 receptors

  摘要：

  A series of C-3 cyclic side-chain analogues of classical cannabinoids were synthesized to probe the ligand binding pocket of the CB1 and CB2 receptors. The analogues were evaluated for CB1 and CB2 receptor binding affinities relative to Delta(8)-THC. The C3 side-chain geometries of the analogues were studied using high field NMR spectroscopy and quantum mechanical calculations. The results of these studies provide insights into the geometry of the ligand binding pocket of the CB1 and CB2 receptors. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00238-4
• 作为产物：
  描述：

  3,5-二甲氧基苯腈 在 三氟化硼乙醚 、 三溴化硼 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 36.5h， 生成 5-(2-butyl-[1,3]dithiolan-2-yl)-benzene-1,3-diol
  参考文献：
  名称：

  Synthesis and testing of novel classical cannabinoids: exploring the side chain ligand binding pocket of the CB1 and CB2 receptors

  摘要：

  A series of C-3 cyclic side-chain analogues of classical cannabinoids were synthesized to probe the ligand binding pocket of the CB1 and CB2 receptors. The analogues were evaluated for CB1 and CB2 receptor binding affinities relative to Delta(8)-THC. The C3 side-chain geometries of the analogues were studied using high field NMR spectroscopy and quantum mechanical calculations. The results of these studies provide insights into the geometry of the ligand binding pocket of the CB1 and CB2 receptors. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00238-4

文献信息

• Cannabinoid derivatives, methods of making, and use thereof
  申请人：——

  公开号：US20040242593A1

  公开（公告）日：2004-12-02

  1′-substituted cannabinoid derivatives of delta-8-tetrahydrocannabinol, delta-9-tetrahydrocannabinol, and delta-6a-10a-tetrahydrocannabinol that have affinity for the cannabinoid receptor type-1 (CB-1) and/or cannabinoid receptor type-2 (CB-2). Compounds having activity as either agonists or antagonists of the CB-1 and/or CB-2 receptors can be used for treating CB-1 or CB-2 mediated conditions.

  1′-取代的大麻素衍生物，包括Δ-8-四氢大麻酚、Δ-9-四氢大麻酚和Δ-6a-10a-四氢大麻酚，它们对大麻素受体类型-1（CB-1）和/或大麻素受体类型-2（CB-2）具有亲和力。具有作为CB-1和/或CB-2受体的激动剂或拮抗剂活性的化合物可用于治疗CB-1或CB-2介导的病症。
• CANNABINOID DERIVATIVES, METHODS OF MAKING, AND USE THEREOF
  申请人：The University of Tennessee Research Foundation

  公开号：EP1633733B1

  公开（公告）日：2011-01-26
• US7169942B2
  申请人：——

  公开号：US7169942B2

  公开（公告）日：2007-01-30
• Synthesis and testing of novel classical cannabinoids: exploring the side chain ligand binding pocket of the CB1 and CB2 receptors
  作者：Asha K Nadipuram、Mathangi Krishnamurthy、Antonio M Ferreira、Wei Li、Bob M Moore

  DOI：10.1016/s0968-0896(03)00238-4

  日期：2003.7

  A series of C-3 cyclic side-chain analogues of classical cannabinoids were synthesized to probe the ligand binding pocket of the CB1 and CB2 receptors. The analogues were evaluated for CB1 and CB2 receptor binding affinities relative to Delta(8)-THC. The C3 side-chain geometries of the analogues were studied using high field NMR spectroscopy and quantum mechanical calculations. The results of these studies provide insights into the geometry of the ligand binding pocket of the CB1 and CB2 receptors. (C) 2003 Elsevier Science Ltd. All rights reserved.