methyl 1-[1-hydroxy-2-(2,4-dimethylphenyl)-2-oxoethyl]cyclopentanecarboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 1-[1-hydroxy-2-(2,4-dimethylphenyl)-2-oxoethyl]cyclopentanecarboxylate
• 英文别名: Methyl 1-[1-hydroxy-2-(2,4-dimethylphenyl)-2-oxoethyl]cyclopentanecarboxylate；methyl 1-[2-(2,4-dimethylphenyl)-1-hydroxy-2-oxoethyl]cyclopentane-1-carboxylate
• 化学式: C₁₇H₂₂O₄
• 分子量: 290.359
• InChiKey: BMMCOXGRJJGOND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-溴环戊烷羧酸甲酯 、 2-(2,4-dimethylphenyl)-2-oxoacetaldehyde 在 锌 作用下， 以 六甲基磷酰三胺 、 乙醚 、 苯 为溶剂， 以65%的产率得到methyl 1-[1-hydroxy-2-(2,4-dimethylphenyl)-2-oxoethyl]cyclopentanecarboxylate
  参考文献：
  名称：

  1-溴环烷羧酸甲酯与α-二羰基化合物的Reformatsky反应

  摘要：

  Reformatsky reactions of methyl 1-bromocyclohexanecarboxylate and methyl 1-bromocyclopentanecarboxylate with 2-aryl-2-oxoacetaidehydes involve both carbonyl groups of the latter and result in formation of 3a-aryl-3,3:6,6-bis(pentamethylene)- and 3a-aryl-3,3:6,6-bis(tetramethylene)tetrahydrofuro-[3,2-b]furan-2,5-diones. The reaction with 2-(2,4-dimethylphenyl)-2-oxoacetaldehyde gives acyclic products, methyl 1-[1-hydroxy-2-(2,4-dimethylphenyl)-2-oxoethyl]cyclohexanecarboxylate and methyl 1-[1-hydroxy-2(2,,4-dimethylphenyl)-2-oxoethyllcyclopentanecarboxylate, while with benzil methyl 1-(4-hydroxy-1-oxo-3,4-diphenyl-2-oxaspiro[4.5]dec-3-yl)cyclohexanecarboxylate and methyl 1-(4-hydroxy-1-oxo-3,4-diphenyl-2-oxaspiro[4.4]non-3-yl)cyclopentanecarboxylate are obtained.

  DOI：

  10.1023/b:rujo.0000045183.34092.05

文献信息

• Reformatsky Reaction of Methyl 1-Bromocycloalkanecarboxylates with  -Dicarbonyl Compounds
  作者：N. F. Kirillov、V. V. Shchepin、L. A. Vedernikova

  DOI：10.1023/b:rujo.0000045183.34092.05

  日期：2004.7

  Reformatsky reactions of methyl 1-bromocyclohexanecarboxylate and methyl 1-bromocyclopentanecarboxylate with 2-aryl-2-oxoacetaidehydes involve both carbonyl groups of the latter and result in formation of 3a-aryl-3,3:6,6-bis(pentamethylene)- and 3a-aryl-3,3:6,6-bis(tetramethylene)tetrahydrofuro-[3,2-b]furan-2,5-diones. The reaction with 2-(2,4-dimethylphenyl)-2-oxoacetaldehyde gives acyclic products, methyl 1-[1-hydroxy-2-(2,4-dimethylphenyl)-2-oxoethyl]cyclohexanecarboxylate and methyl 1-[1-hydroxy-2(2,,4-dimethylphenyl)-2-oxoethyllcyclopentanecarboxylate, while with benzil methyl 1-(4-hydroxy-1-oxo-3,4-diphenyl-2-oxaspiro[4.5]dec-3-yl)cyclohexanecarboxylate and methyl 1-(4-hydroxy-1-oxo-3,4-diphenyl-2-oxaspiro[4.4]non-3-yl)cyclopentanecarboxylate are obtained.