2-Phenyl-3-isopropoxy-2-cyclobutenone

• 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: 2-Phenyl-3-isopropoxy-2-cyclobutenone
• 英文别名: 3-Isopropoxy-2-phenyl-2-cyclobutenone；2-Phenyl-3-propan-2-yloxycyclobut-2-en-1-one
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: GGJYVNQEZYFQFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Semiquadratsaeure-i-propylester 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.33h， 生成 2-Phenyl-3-isopropoxy-2-cyclobutenone
  参考文献：
  名称：

  Regioselective Synthesis of Highly Substituted Naphthols

  摘要：

  2,3,4-Trisubstituted 4-hydroxy-2-cyclobutenones, prepared by regiospecific synthesis of substituted cyclobutenediones, undergo Lewis acid facilitated ionization to cyclobutenyl cations, which are trapped by trialkylsilanes in a regioselective sense. Thermolysis of the resulting cyclobutenones affords phenols in high yields.

  DOI：

  10.1021/jo00108a029

文献信息

• Synthesis of .alpha.-Pyridone-Based Azaheteroaromatics by Intramolecular Vinylketene Cyclizations onto the C:N Bond of Nitrogen Heteroaromatics
  作者：Angela Gurski Birchler、Fuqiang Liu、Lanny S. Liebeskind

  DOI：10.1021/jo00104a033

  日期：1994.12

  Substituted quinolizin-4-ones and ring-fused alpha-pyridone derivatives have been synthesized by the construction of 2,3-disubstituted-4-(2-azaheteroaryl)-2-cyclobutenones followed by thermal rearrangment. 4-(2-Azaheteroaryl)-2-cyclobutenones have been prepared regioselectively by the addition of 2-lithioazaheteroaromatics to cyclobutenediones and by palladium catalyzed cross-coupling of 4-chloro-2-cyclobutenones with 2-tri-n-stannylazaheteroaromatics. The thermal transformation is proposed to occur by ring-opening of the cyclobutenone followed by intramolecular cyclization of the transient vinylketene onto the carbon-nitrogen double bond of the azaheteroaromatic. A variety of quinolizin-4-ones, imidazo [1,2-a]pyridin-5-ones, 1-oxopyrido[2,1-b]benzothiazoles, and thiazolo[3,2-a]pyridin-5-ones were prepared.
• Turnbull Philip, Moore Harold W., J. Org. Chem, 60 Nr.3 (1995) , S 644-649
  作者：Turnbull Philip, Moore Harold W.

  DOI：——

  日期：——
• Regioselective Synthesis of Highly Substituted Naphthols
  作者：Philip Turnbull、Harold W. Moore

  DOI：10.1021/jo00108a029

  日期：1995.2

  2,3,4-Trisubstituted 4-hydroxy-2-cyclobutenones, prepared by regiospecific synthesis of substituted cyclobutenediones, undergo Lewis acid facilitated ionization to cyclobutenyl cations, which are trapped by trialkylsilanes in a regioselective sense. Thermolysis of the resulting cyclobutenones affords phenols in high yields.