1-hydroxy-[7,8-(3)H2]-octan-3-one | 245440-55-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-hydroxy-[7,8-(3)H2]-octan-3-one
• CAS: 245440-55-5
• 化学式: C₈H₁₆O₂
• 分子量: 148.198
• InChiKey: VGFJNJIGFHOBEJ-RVQWGROCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  10.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-hydroxy-[7,8-(3)H2]-octan-3-one 在 氨 、 碘 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 3-(2-hydroxyethyl)-3-[4,5-(3)H2]-n-pentyldiazirine
  参考文献：
  名称：

  Synthesis and Properties of 3-(2-Hydroxyethyl)-3-n-pentyldiazirine, a Photoactivable General Anesthetic

  摘要：

  To overcome the difficulties of locating the molecular sites of general anesthetic action, we synthesized a novel photoactivable general anesthetic, 3-(2-hydroxyethyl)-3-n-pentyldiazirine (3-diazirinyloctanol), which anesthetized tadpoles with an ED50 of 160 mu M. Subanesthetic concentrations of 3-diazirinyloctanol enhanced GABA-induced currents in GABA(A) receptors, an effect that has been implicated in general anesthetic action. It also enhanced [H-3]muscimol binding to this receptor. In muscle nicotinic acetylcholine receptors (nAcChoR), it inhibited the response to acetylcholine with an IC50 of 33 mu M. 3-Diazirinyloctanol's pharmacological actions were comparable to those of octanol. 3-(2-Hydroxyethyl)-3-[4,5-H-3(2)]-n-pentyldiazirine photoincorporated into Torpedo nAcChoR-rich membranes mainly in the alpha subunit with 70% being in a proteolytic fragment containing the M4 transmembrane segment. Agonist enhanced the photolabeling 10-fold in a fragment containing the M1, M2, and M3 transmembrane segments. Thus, 3-diazirinyloctanol is a novel general anesthetic that acts on, and can be photoincorporated into, postsynaptic receptors.

  DOI：

  10.1021/jm9806300
• 作为产物：
  描述：

  3-Oxo-7-octen-1-ol 在 palladium on activated charcoal 超重氢 作用下， 生成 1-hydroxy-[7,8-(3)H2]-octan-3-one
  参考文献：
  名称：

  Synthesis and Properties of 3-(2-Hydroxyethyl)-3-n-pentyldiazirine, a Photoactivable General Anesthetic

  摘要：

  To overcome the difficulties of locating the molecular sites of general anesthetic action, we synthesized a novel photoactivable general anesthetic, 3-(2-hydroxyethyl)-3-n-pentyldiazirine (3-diazirinyloctanol), which anesthetized tadpoles with an ED50 of 160 mu M. Subanesthetic concentrations of 3-diazirinyloctanol enhanced GABA-induced currents in GABA(A) receptors, an effect that has been implicated in general anesthetic action. It also enhanced [H-3]muscimol binding to this receptor. In muscle nicotinic acetylcholine receptors (nAcChoR), it inhibited the response to acetylcholine with an IC50 of 33 mu M. 3-Diazirinyloctanol's pharmacological actions were comparable to those of octanol. 3-(2-Hydroxyethyl)-3-[4,5-H-3(2)]-n-pentyldiazirine photoincorporated into Torpedo nAcChoR-rich membranes mainly in the alpha subunit with 70% being in a proteolytic fragment containing the M4 transmembrane segment. Agonist enhanced the photolabeling 10-fold in a fragment containing the M1, M2, and M3 transmembrane segments. Thus, 3-diazirinyloctanol is a novel general anesthetic that acts on, and can be photoincorporated into, postsynaptic receptors.

  DOI：

  10.1021/jm9806300