ethoxymethyl ether salvinorin B | 1017524-76-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: ethoxymethyl ether salvinorin B
• 英文别名: salvinorin B ethoxymethyl ether；methyl (2S,4aR,6aR,7R,9S,10aS,10bR)-9-(ethoxymethoxy)-2-(furan-3-yl)-6a,10b-dimethyl-4,10-dioxo-2,4a,5,6,7,8,9,10a-octahydro-1H-benzo[f]isochromene-7-carboxylate
• CAS: 1017524-76-3
• 化学式: C₂₄H₃₂O₈
• 分子量: 448.513
• InChiKey: ICVTXAUKIHJDGV-WFOQEEKOSA-N

物化性质

• 沸点：
  567.2±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  101
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  SALVINORINB(品牌:CAYMAN进口) 、 氯甲基乙醚 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以80%的产率得到ethoxymethyl ether salvinorin B
  参考文献：
  名称：

  Standard protecting groups create potent and selective κ opioids: Salvinorin B alkoxymethyl ethers

  摘要：

  Protection of salvinorin B as standard alkoxyalkyl ethers yielded highly potent kappa opioid receptor agonists. Ethoxymethyl ether 6 is among the most potent and Selective kappa agonists reported to date. Fluoroethoxymethyl ether 11 is the first potent, selective fluorinated kappa ligand, with potential use in MRI and PET studies. Further enlargement of the alkoxy group, alkylation of the acetal carbon, or heteroatom substitution all reduced activity. These protecting groups may prove useful in related work not only by enabling the use of harsher synthetic conditions, but potentially by optimizing the potency of the products. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.10.067

文献信息

• Standard protecting groups create potent and selective κ opioids: Salvinorin B alkoxymethyl ethers
  作者：Thomas A. Munro、Katharine K. Duncan、Wei Xu、Yulin Wang、Lee-Yuan Liu-Chen、William A. Carlezon Jr.、Bruce M. Cohen、Cécile Béguin

  DOI：10.1016/j.bmc.2007.10.067

  日期：2008.2.1

  Protection of salvinorin B as standard alkoxyalkyl ethers yielded highly potent kappa opioid receptor agonists. Ethoxymethyl ether 6 is among the most potent and Selective kappa agonists reported to date. Fluoroethoxymethyl ether 11 is the first potent, selective fluorinated kappa ligand, with potential use in MRI and PET studies. Further enlargement of the alkoxy group, alkylation of the acetal carbon, or heteroatom substitution all reduced activity. These protecting groups may prove useful in related work not only by enabling the use of harsher synthetic conditions, but potentially by optimizing the potency of the products. (c) 2007 Elsevier Ltd. All rights reserved.