2,6-Dimethoxy-4-(2-methylpentan-2-yl)phenol | 180415-81-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,6-Dimethoxy-4-(2-methylpentan-2-yl)phenol
• 英文别名: 2,6-dimethoxy-4-(2-methylpentan-2-yl)phenol
• CAS: 180415-81-0
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: MBFCYLBQNUKRKM-UHFFFAOYSA-N

物化性质

• 沸点：
  333.8±42.0 °C(Predicted)
• 密度：
  1.011±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 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：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-Dimethoxy-4-(2-methylpentan-2-yl)phenol 在 氨 、 三溴化硼 、 lithium 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 为溶剂， 生成 (6aR,10aR)-6,6,9-trimethyl-3-(2-methylpentan-2-yl)-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-1-ol
  参考文献：
  名称：

  Structure–activity relationships for 1′,1′-dimethylalkyl-Δ 8 -tetrahydrocannabinols

  摘要：

  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.

  DOI：

  10.1016/s0968-0896(02)00649-1
• 作为产物：
  描述：

  2,6-二甲氧基苯酚 、 2-甲基-2-戊醇 在 甲烷磺酸 作用下， 以92%的产率得到2,6-Dimethoxy-4-(2-methylpentan-2-yl)phenol
  参考文献：
  名称：

  Structure–activity relationships for 1′,1′-dimethylalkyl-Δ 8 -tetrahydrocannabinols

  摘要：

  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.

  DOI：

  10.1016/s0968-0896(02)00649-1

文献信息

• Neuroprotective (+) 3S, 4S cannabinoids with modified 5′-side chain
  作者：Emil Pop、Clinton E. Browne、Varda Nadler、Anat Biegon、Marcus E. Brewster

  DOI：10.1016/s0960-894x(96)00272-7

  日期：1996.7

  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
• 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.