4-Hydroxy-3-isopropoxy-2,4-dimethyl-2-cyclobutenone | 151664-46-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-Hydroxy-3-isopropoxy-2,4-dimethyl-2-cyclobutenone
• 英文别名: 4-hydroxy-3-isopropoxy-2,4-dimethylcyclobut-2-enone；4-hydroxy-2,4-dimethyl-3-propan-2-yloxycyclobut-2-en-1-one
• CAS: 151664-46-9
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: YNZXNYBJZXWNND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.02
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-Hydroxy-3-isopropoxy-2,4-dimethyl-2-cyclobutenone 在 四氯化碳 、 四乙基氯化铵 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以75%的产率得到4-Chloro-3-isopropoxy-2,4-dimethyl-2-cyclobutenone
  参考文献：
  名称：

  A general, regioselective synthesis of substituted benzocyclobutenedione monoacetals

  摘要：

  A general, regioselective synthesis of substituted benzocyclobutenedione monoacetals is reported. Palladium-catalyzed coupling of a variety of 4-chlorocyclobutenones with 3-(tri-n-butylstannyl)-3-cyclobutene-1,2-dione 2-(ethylene acetal) and heating up to 70-100-degrees-C produces substituted benzocyclobutenedione monoacetals in good to excellent yields. Thia chemistry is presumed to proceed through palladium-catalyzed formation of a 3-(1-oxo-2-cyclobuten-4-yl)-3-cyclobutene-1,2-dione-2-(ethylene acetal) followed by a thermally induced ring opening to a dienyl ketene and subsequent six-electron electrocyclic ring closure and tautomerization. 2,3-Disubstituted 4-chlorocyclobutenones afford palladium intermediates which couple exclusively at the least-substituted allylic terminus. 2,3,4-Trisubstituted 4-chlorocyclobutenones have not been studied in detail; however, preliminary results suggest that regioselective allylic cross-coupling can be achieved. The methodology described provides an expedient and efficient route to previously difficult-to-prepare benzocyclobutenedione derivatives. These function as important synthetic intermediates in a variety of reactions developed in these and other laboratories.

  DOI：

  10.1021/jo00067a029
• 作为产物：
  描述：

  3,4-二异丙氧基-3-环丁烯-1,2-二酮 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.25h， 生成 4-Hydroxy-3-isopropoxy-2,4-dimethyl-2-cyclobutenone
  参考文献：
  名称：

  α-羟基环丁烯酮的四电子环开环/分子间[4 + 2]环加成：多种取代δ-内酰胺的立体选择性合成。

  摘要：

  报道了α-羟基环丁烯酮的四电子开环/分子间[4 + 2]环加成反应。该反应代表了广泛研究的烯醇-烯酮中间体的分子间环加成反应的第一个实例，并为在高立体选择性下取代取代的δ-内酰胺提供了一条新的合成途径。

  DOI：

  10.1002/adsc.201501152