3-methoxy-4-(1-pentynyl)-3-cyclobutene-1,2-dione | 137395-31-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-methoxy-4-(1-pentynyl)-3-cyclobutene-1,2-dione
• 英文别名: 3-methoxy-4-pent-1-ynylcyclobut-3-ene-1,2-dione
• CAS: 137395-31-4
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: SMUFTDANMHHNEY-UHFFFAOYSA-N

物化性质

• 沸点：
  277.3±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.44
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-pentynyl lithium 、 3-methoxy-4-(1-pentynyl)-3-cyclobutene-1,2-dione 以 四氢呋喃 为溶剂， 反应 0.25h， 以87%的产率得到4-hydroxy-3-methoxy-2,4-di-1-pentynyl-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

文献信息

• 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.