2-[4-(oxiran-2-yl)but-2-ynoxy]oxane | 122951-70-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-[4-(oxiran-2-yl)but-2-ynoxy]oxane
• CAS: 122951-70-6
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: XEBSMBBVGOXCLJ-UHFFFAOYSA-N

物化性质

• 沸点：
  331.1±32.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  30.99
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-[4-(oxiran-2-yl)but-2-ynoxy]oxane 在 甲醇 、 4-二甲氨基吡啶 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 potassium carbonate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 [6-(Benzenesulfonyl)-1-(2-nitroimidazol-1-yl)hex-4-yn-2-yl] acetate
  参考文献：
  名称：

  Propargylic sulfones possessing a 2-nitroimidazole function: novel hypoxic-cell radiosensitizers with intracellular non-protein thiol depletion ability

  摘要：

  Propargylic sulfones (1a-c) containing a 2-nitroimidazole structure were synthesized, and their non-protein thiol (NPSH) depletion abilities were investigated. Propargylic sulfones la,c containing an electron withdrawing p-nitrophenyl group showed high reactivity toward capturing glutathione (GSH), a typical intracellular NPSH, in phosphate buffer. Among the three propargylic sulfones 1a-c, carboxylic acid derivative 1c showed the most potent radiosensitizing activity toward hypoxic EMT6/KU tumor cells. In view of these results and the partition coefficients between 1-octanol and water, we concluded that appropriate NPSH-depletion ability and lipophilicity are both important in achieving potent hypoxic-cell radiosensitization by propargylic sulfones possessing a 2-nitroimidazole function in biological systems. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.060
• 作为产物：
  描述：

  1-Chloro-6-(tetrahydro-pyran-2-yloxy)-hex-4-yn-2-ol 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以74%的产率得到2-[4-(oxiran-2-yl)but-2-ynoxy]oxane
  参考文献：
  名称：

  Nicolaou, K. C.; Skokotas, G.; Maligres, P., Angewandte Chemie, 1989, vol. 101, # 9, p. 1255 - 1257

  摘要：

  DOI：

文献信息

• NICOLAOU, K. C.;SKOKOTAS, G.;MALIGRES, P.;ZUCCARELLO, G.;SCHWEIGER, E. J.+, ANGEW. CHEM., 101,(1989) N, C. 1255-1257
  作者：NICOLAOU, K. C.、SKOKOTAS, G.、MALIGRES, P.、ZUCCARELLO, G.、SCHWEIGER, E. J.+

  DOI：——

  日期：——
• Propargylic sulfones possessing a 2-nitroimidazole function: novel hypoxic-cell radiosensitizers with intracellular non-protein thiol depletion ability
  作者：Kazuhito Tanabe、Ryusuke Kojima、Hiroshi Hatta、Sei-ichi Nishimoto

  DOI：10.1016/j.bmcl.2004.02.060

  日期：2004.5

  Propargylic sulfones (1a-c) containing a 2-nitroimidazole structure were synthesized, and their non-protein thiol (NPSH) depletion abilities were investigated. Propargylic sulfones la,c containing an electron withdrawing p-nitrophenyl group showed high reactivity toward capturing glutathione (GSH), a typical intracellular NPSH, in phosphate buffer. Among the three propargylic sulfones 1a-c, carboxylic acid derivative 1c showed the most potent radiosensitizing activity toward hypoxic EMT6/KU tumor cells. In view of these results and the partition coefficients between 1-octanol and water, we concluded that appropriate NPSH-depletion ability and lipophilicity are both important in achieving potent hypoxic-cell radiosensitization by propargylic sulfones possessing a 2-nitroimidazole function in biological systems. (C) 2004 Elsevier Ltd. All rights reserved.
• Nicolaou, K. C.; Skokotas, G.; Maligres, P., Angewandte Chemie, 1989, vol. 101, # 9, p. 1255 - 1257
  作者：Nicolaou, K. C.、Skokotas, G.、Maligres, P.、Zuccarello, G.、Schweiger, E. J.、et al.

  DOI：——

  日期：——