4-hydroxy-3-methoxy-4-methyl-2-phenyl-2-cyclobuten-1-one | 137394-95-7

• 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: 4-hydroxy-3-methoxy-4-methyl-2-phenyl-2-cyclobuten-1-one
• 英文别名: 4-hydroxy-3-methoxy-4-methyl-2-phenylcyclobut-2-enone；4-Hydroxy-3-methoxy-4-methyl-2-phenylcyclobut-2-en-1-one
• CAS: 137394-95-7
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: RVTVWIRRUYKCSO-UHFFFAOYSA-N

物化性质

• 沸点：
  374.7±42.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3-methoxy-4-methyl-2-phenyl-2-cyclobuten-1-one 在 吡啶 、 氯化亚砜 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 10.17h， 生成 3-methoxy-4-methyl-2-phenyl-4-(phenylthio)-2-cyclobuten-1-one
  参考文献：
  名称：

  Synthesis of p-chlorophenols (and -naphthols) from the thermal rearrangement of 4-chlorocyclobutenones

  摘要：

  A systematic study of the reaction of 4-hydroxycyclobutenones with thionyl chloride is reported. A useful model evolves from this study which allows the prediction of the site of chlorination for unsymmetrical examples. The chlorination is envisaged to involve the corresponding homoaromatic carbocation, and the site of chlorination takes place preferentially at the position substituted with the greater cation-stabilizing substituent. Specifically, this follows the general order of allyl > benzyl > alkyl > propargyl. The 4-chlorocyclobutenones prepared in this study were shown to be useful synthetic precursors to highly substituted chlorophenols and chloronaphthols.

  DOI：

  10.1021/jo00027a057
• 作为产物：
  描述：

  甲基锂 、 3-methoxy-4-phenylcyclobutenedione 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 4-hydroxy-3-methoxy-4-methyl-2-phenyl-2-cyclobuten-1-one
  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

文献信息

• Four-Electron Electrocyclic Ring-Opening/Intermolecular [4+2] Cycloadditions of α-Hydroxycyclobutenones: Stereoselective Synthesis of Multiple Substituted δ-Lactams
  作者：Peidong Song、Qing Li、Congcong Wang、Wenfa Wu、Xu Mao、Jiajia Wang、Xiangdong Hu

  DOI：10.1002/adsc.201501152

  日期：2016.4.14

  four‐electron electrocyclic ring‐opening/intermolecular [4+2] cycloaddition of α‐hydroxycyclobutenones is reported. The reaction represents the first example for the intermolecular cycloaddition of the extensively studied enol‐ketene intermediate, and provides a new synthetic route to multiply substituted δ‐lactams in high stereoselectivity.

  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。
• Synthesis of p-chlorophenols (and -naphthols) from the thermal rearrangement of 4-chlorocyclobutenones
  作者：Simon L. Xu、Harold W. Moore

  DOI：10.1021/jo00027a057

  日期：1992.1

  A systematic study of the reaction of 4-hydroxycyclobutenones with thionyl chloride is reported. A useful model evolves from this study which allows the prediction of the site of chlorination for unsymmetrical examples. The chlorination is envisaged to involve the corresponding homoaromatic carbocation, and the site of chlorination takes place preferentially at the position substituted with the greater cation-stabilizing substituent. Specifically, this follows the general order of allyl > benzyl > alkyl > propargyl. The 4-chlorocyclobutenones prepared in this study were shown to be useful synthetic precursors to highly substituted chlorophenols and chloronaphthols.