bis(pentachlorophenyl)ketene methyl isopropyl acetal | 107846-84-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis(pentachlorophenyl)ketene methyl isopropyl acetal
• 英文别名: 1,2,3,4,5-Pentachloro-6-[2-methoxy-1-(2,3,4,5,6-pentachlorophenyl)-2-propan-2-yloxyethenyl]benzene
• CAS: 107846-84-4
• 化学式: C₁₈H₁₀Cl₁₀O₂
• 分子量: 612.806
• InChiKey: AMIGKIDZVGCDMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  草酸二异丙酯 在 三溴化磷 、 sodium hydride 、 magnesium 、 1,2-二溴乙烷 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 2.0h， 生成 bis(pentachlorophenyl)ketene methyl isopropyl acetal
  参考文献：
  名称：

  Synthesis of the sterically hindered bis(pentachlorophenyl)acetic acid and derived stable free radicals

  摘要：

  Bis(pentachlorophenyl)acetic acid esters were synthesized from the alpha-hydroxydiaryl acetate esters 13 via the free radicals 15 formed on homolytic cleavage of the alpha-chloro compounds 14. The acid 8 underwent rapid decarboxylation in basic solution (e.g., Et3N in THF) but could be dehydrated to the corresponding ketene 17. Nucleophilic addition to the ketene provided a route to the corresponding amides (21 and 19) and nitrile 20, the enolates of which underwent ready oxidation to the corresponding stable free radicals 15, 22, and 23. Evidence for the structure and unusual stability of these free radicals is presented. Attempts to observe enols of acids or esters on the addition of water or alcohols to the sterically hindered ketene 17 were unsuccessful.

  DOI：

  10.1021/jo00042a021

文献信息

• Regiospecificity in the alkylation of ester enolates: synthesis of sterically hindered diarylketene acetals
  作者：P. O'Neill、A. F. Hegarty

  DOI：10.1021/jo00386a046

  日期：1987.5
• ONEILL P.; HEGARTY A. F., J. ORG. CHEM., 52,(1987) N 10, 2113-2114
  作者：ONEILL P.、 HEGARTY A. F.

  DOI：——

  日期：——
• Synthesis of the sterically hindered bis(pentachlorophenyl)acetic acid and derived stable free radicals
  作者：Pat O'Neill、Anthony F. Hegarty

  DOI：10.1021/jo00042a021

  日期：1992.7

  Bis(pentachlorophenyl)acetic acid esters were synthesized from the alpha-hydroxydiaryl acetate esters 13 via the free radicals 15 formed on homolytic cleavage of the alpha-chloro compounds 14. The acid 8 underwent rapid decarboxylation in basic solution (e.g., Et3N in THF) but could be dehydrated to the corresponding ketene 17. Nucleophilic addition to the ketene provided a route to the corresponding amides (21 and 19) and nitrile 20, the enolates of which underwent ready oxidation to the corresponding stable free radicals 15, 22, and 23. Evidence for the structure and unusual stability of these free radicals is presented. Attempts to observe enols of acids or esters on the addition of water or alcohols to the sterically hindered ketene 17 were unsuccessful.