syn-(methyl,chloro)(methyl,ethynyl)bimane | 181298-25-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: syn-(methyl,chloro)(methyl,ethynyl)bimane
• 英文别名: 6-chloro-2-ethynyl-1,7-dimethylpyrazolo[1,2-a]pyrazole-3,5-dione
• CAS: 181298-25-9
• 化学式: C₁₀H₇ClN₂O₂
• 分子量: 222.631
• InChiKey: KMZBJKMMURAWEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  syn-(methyl,chloro)(methyl,ethynyl)bimane 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 三丁基氯化锡 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以40%的产率得到6-Chloro-2-[4-(6-chloro-1,7-dimethyl-3,5-dioxopyrazolo[1,2-a]pyrazol-2-yl)buta-1,3-diynyl]-1,7-dimethylpyrazolo[1,2-a]pyrazole-3,5-dione
  参考文献：
  名称：

  Bimane Acetylenes and Diacetylenes. Bimanes. 33

  摘要：

  Two series (4,6-dihydro and 4,6-dimethyl) of syn-bimanes [1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-diones] have been converted to acetylene and diacetylene derivatives. Their chemical and photophysical properties are reported. The 3-(and 6-)iodo (diiodo) derivatives are the best choices for Stille or Heck condensations with acetylenes or acrylates. Desilylation of (trimethylsilyl)acetylenes is best carried out with silver nitrate followed by lithium bromide. The acetylenes and diacetylenes are quite stable and highly fluorescent and represent candidate units for incorporation into polymers.

  DOI：

  10.1021/jo951830b
• 作为产物：
  描述：

  syn-(methyl,chloro)(methyl,(trimethylsilyl)ethynyl)bimane 在 silver nitrate 、 水 、 lithium bromide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以65%的产率得到syn-(methyl,chloro)(methyl,ethynyl)bimane
  参考文献：
  名称：

  Bimane Acetylenes and Diacetylenes. Bimanes. 33

  摘要：

  Two series (4,6-dihydro and 4,6-dimethyl) of syn-bimanes [1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-diones] have been converted to acetylene and diacetylene derivatives. Their chemical and photophysical properties are reported. The 3-(and 6-)iodo (diiodo) derivatives are the best choices for Stille or Heck condensations with acetylenes or acrylates. Desilylation of (trimethylsilyl)acetylenes is best carried out with silver nitrate followed by lithium bromide. The acetylenes and diacetylenes are quite stable and highly fluorescent and represent candidate units for incorporation into polymers.

  DOI：

  10.1021/jo951830b