4-Hydroxy-4-(3-trimethylsilanyl-prop-2-ynyl)-cyclopent-2-enone | 678143-41-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Hydroxy-4-(3-trimethylsilanyl-prop-2-ynyl)-cyclopent-2-enone
• 英文别名: 4-hydroxy-4-(3-trimethylsilylprop-2-ynyl)cyclopent-2-en-1-one
• CAS: 678143-41-4
• 化学式: C₁₁H₁₆O₂Si
• 分子量: 208.332
• InChiKey: PTDHCFXSYAPWDZ-UHFFFAOYSA-N

物化性质

• 沸点：
  293.1±40.0 °C(Predicted)
• 密度：
  1.059±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  4-Hydroxy-4-(3-trimethylsilanyl-prop-2-ynyl)-cyclopent-2-enone 在 吡啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 双(三甲基硅烷基)氨基钾 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 [(5E)-5-benzylidene-4-oxo-1-(3-phenylprop-2-ynyl)cyclopent-2-en-1-yl] acetate
  参考文献：
  名称：

  Effective irreversible alkylating reagents based on the structure of clavulones

  摘要：

  We describe the design and synthesis of alkylating reagents based on the structure of clavulones. They are composed of cross-conjugated dienone system and irreversibly reacted with two nucleophiles under mildly basic conditions via beta-elimination. Hydroxyl derivative 7b showed the highest reactivity toward thiols and showed the strongest cytotoxicity in Hela S3 cells among the three derivatives having a different protecting group at the tert-hydroxyl group. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.026
• 作为产物：
  描述：

  1-[3-(三甲基硅烷基)-2-丙炔-1-基]-4-环戊烯-1,3-二醇 在 manganese(IV) oxide 作用下， 以 乙醚 为溶剂， 以71%的产率得到4-Hydroxy-4-(3-trimethylsilanyl-prop-2-ynyl)-cyclopent-2-enone
  参考文献：
  名称：

  Effective irreversible alkylating reagents based on the structure of clavulones

  摘要：

  We describe the design and synthesis of alkylating reagents based on the structure of clavulones. They are composed of cross-conjugated dienone system and irreversibly reacted with two nucleophiles under mildly basic conditions via beta-elimination. Hydroxyl derivative 7b showed the highest reactivity toward thiols and showed the strongest cytotoxicity in Hela S3 cells among the three derivatives having a different protecting group at the tert-hydroxyl group. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.026