methyl 1-methyl-4-methylenespiropentane-1-carboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 1-methyl-4-methylenespiropentane-1-carboxylate
• 英文别名: methyl (2S,3S)-2-methyl-5-methylidenespiro[2.2]pentane-2-carboxylate
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: IXBRAKVJQXXLFI-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 methyl 1-methyl-4-methylenespiropentane-1-carboxylate 、 methyl 1-methyl-4-methylenespiropentane-1-carboxylate 在 palladium diacetate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成 methyl 1-methyldispiro[2.0.2]heptane-1-carboxylate 、 methyl 1-methyldispiro[2.0.2]heptane-1-carboxylate
  参考文献：
  名称：

  Generation of diazo-2-methylenecyclopropane and its 1,3-dipolar cycloaddition to acrylates

  摘要：

  N-(2-Methylenecyclopropyl)-N-nitrosourea (2) was synthesized for the first time (yield 70%) and its decomposition induced by bases was studied. In particular, treatment with MeONa/MeOH at -30 degrees C in the presence of methyl methacrylate gives the corresponding 1-pyrazoline stereoisomers, the products of [3+2]-cycloaddition of diazo-2-methylene-cyclopropane (1) generated in situ. Decomposition of 2 on treatment with K2CO3 at 0-5 degrees C in the presence of acrylonitrile also proceeds as [3+2]-cycloaddition; however, the expected 2-pyrazoline easily isomerizes into 5(3)-isopropenyl-3(5)-cyanopyrazole. Buta-1,2,3-triene is the main product of base-induced decomposition of 2 in the absence of unsaturated substrates.

  DOI：

  10.1007/bf02495762
• 作为产物：
  描述：

  6-methoxycarbonyl-6-methyl-1-methylene-4,5-diazaspiro-[2.4]hept-4-ene 、 6-methoxycarbonyl-6-methyl-1-methylene-4,5-diazaspiro-[2.4]hept-4-ene 以 苯 为溶剂， 生成 methyl 1-methyl-4-methylenespiropentane-1-carboxylate 、 methyl 1-methyl-4-methylenespiropentane-1-carboxylate
  参考文献：
  名称：

  Generation of diazo-2-methylenecyclopropane and its 1,3-dipolar cycloaddition to acrylates

  摘要：

  N-(2-Methylenecyclopropyl)-N-nitrosourea (2) was synthesized for the first time (yield 70%) and its decomposition induced by bases was studied. In particular, treatment with MeONa/MeOH at -30 degrees C in the presence of methyl methacrylate gives the corresponding 1-pyrazoline stereoisomers, the products of [3+2]-cycloaddition of diazo-2-methylene-cyclopropane (1) generated in situ. Decomposition of 2 on treatment with K2CO3 at 0-5 degrees C in the presence of acrylonitrile also proceeds as [3+2]-cycloaddition; however, the expected 2-pyrazoline easily isomerizes into 5(3)-isopropenyl-3(5)-cyanopyrazole. Buta-1,2,3-triene is the main product of base-induced decomposition of 2 in the absence of unsaturated substrates.

  DOI：

  10.1007/bf02495762