(1R,2S)-2-thiophen-3-yl-1,2,3,4-tetrahydronaphthalen-1-ol | 1144040-79-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,2S)-2-thiophen-3-yl-1,2,3,4-tetrahydronaphthalen-1-ol
• CAS: 1144040-79-8
• 化学式: C₁₄H₁₄OS
• 分子量: 230.331
• InChiKey: ZMYBDUXHOPZEAL-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-thiophen-3-yl-1,2,3,4-tetrahydronaphthalen-1-ol 在 叠氮磷酸二苯酯 、 三苯基膦 、 sodium chloride 、 偶氮二甲酸二乙酯 作用下， 以 甲苯 为溶剂， 以63%的产率得到3-[(1S,2S)-1-azido-1,2,3,4-tetrahydronaphthalen-2-yl]thiophene
  参考文献：
  名称：

  Discovery of μ-opioid selective ligands derived from 1-aminotetralin scaffolds made via metal-catalyzed ring-opening reactions

  摘要：

  A series of 1-aminotetralin scaffolds was synthesized via metal-catalyzed ring-opening reactions of heterobicyclic alkenes. Small libraries of amides and amines were made using the amino group of each scaffold as a handle. Screening of these libraries against human opioid receptors led to the identification of (S)-(S)-5.2a as a high-affinity selective mu ligand (IC50 mu = 5 nM, kappa = 707 nM, delta = 3,795 nM) displaying mu-agonist/antagonist properties due to its partial agonism (EC50 = 2.6 mu M; E-max = 18%). Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.095
• 作为产物：
  描述：

  (1R,2S)-2-(thiophen-3-yl)-1,2-dihydronaphthalen-1-ol 在 sodium periodate 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 生成 (1R,2S)-2-thiophen-3-yl-1,2,3,4-tetrahydronaphthalen-1-ol
  参考文献：
  名称：

  Discovery of μ-opioid selective ligands derived from 1-aminotetralin scaffolds made via metal-catalyzed ring-opening reactions

  摘要：

  A series of 1-aminotetralin scaffolds was synthesized via metal-catalyzed ring-opening reactions of heterobicyclic alkenes. Small libraries of amides and amines were made using the amino group of each scaffold as a handle. Screening of these libraries against human opioid receptors led to the identification of (S)-(S)-5.2a as a high-affinity selective mu ligand (IC50 mu = 5 nM, kappa = 707 nM, delta = 3,795 nM) displaying mu-agonist/antagonist properties due to its partial agonism (EC50 = 2.6 mu M; E-max = 18%). Crown Copyright (C) 2008 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.095