methyl 2-oxocyclopentanecarboxylate | 1830-92-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基酸
• 英文名称: methyl 2-oxocyclopentanecarboxylate
• 英文别名: 2-Hydroxy-cylopenten-(1)-carbonsaeure-(1)-methylester；Methyl-2-oxocyclopentan-1-carboxylat；Methyl 2-hydroxycyclopentene-1-carboxylate
• CAS: 1830-92-8
• 化学式: C₇H₁₀O₃
• 分子量: 142.155
• InChiKey: PCTQYRLRFUJDQU-UHFFFAOYSA-N

物化性质

• 沸点：
  226.1±40.0 °C(Predicted)
• 密度：
  1.262±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 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：

  methyl 2-oxocyclopentanecarboxylate 在 bis(triphenylphosphine)nickel(II) chloride 、 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 13.25h， 生成 methyl 1-(2'-phenyl-1'-cyclopentene)carboxylate
  参考文献：
  名称：

  Scope and limitation of the nickel-catalyzed coupling reaction between lithium borates and mesylates

  摘要：

  Coupling reaction of aryl borates and mesylates derived from phenols and enols was studied. Mesylates with an electron-withdrawing group or ring were highly reactive at room temperature in the presence of NiCl2(PPh3)(2) to furnish the coupling products in good yields. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(02)01174-9
• 作为产物：
  描述：

  2-diazocyclohexane-1,3-dione 以 四氯化碳 为溶剂， 反应 0.17h， 生成 methyl 2-oxocyclopentanecarboxylate
  参考文献：
  名称：

  Direct observation of .alpha.-oxo ketenes from the photolysis of .alpha.-diazo .beta.-diketones

  摘要：

  Monitoring by IR spectroscopy of the broad-band irradiation of the symmetrically substituted 2-diazo-cyclohexane-1,3-dione (I 1), 3-diazopentane-2,4-dione (19), and 4-diazo-2,2,6,6-tetramethylheptane-3,5-dione (24) in Ar matrices at 12 K showed the formation of 2-carbonylcyclopentanone (s-Z-12), acetyl(methyl)ketene (s-E-20), and tert-butyl(pivaloyl)ketene (s-E-25), respectively, in less than 10 min. On increasing the photolysis time to >3 h, the alpha-oxo ketenes 12,20, and 25 decarbonylated to the corresponding oxocarbenes which underwent Wolff rearrangement to carbonylcyclobutane (15), dimethylketene (23), and di-tert-butylketene (28), respectively. The reaction of 2-carbonylcyclopentanone (12) with CH3OH was monitored by IR spectroscopy. Thus, it was found that the reaction started at ca. 100 K and was essentially complete at 140 K, involving the initial formation of the enol form (9) of methyl 2-oxocyclopentanecarboxylate.

  DOI：

  10.1021/jo00044a019