2,2-dimethylcyclopropane-1,1-dicarboxylic acid methyl ester | 159279-64-8

• 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: 2,2-dimethylcyclopropane-1,1-dicarboxylic acid methyl ester
• 英文别名: 1-(Methoxycarbonyl)-2,2-dimethylcyclopropane-1-carboxylic acid；1-methoxycarbonyl-2,2-dimethylcyclopropane-1-carboxylic acid
• CAS: 159279-64-8
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: BQQUKQWMWSOGHV-UHFFFAOYSA-N

物化性质

• 沸点：
  248.1±23.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-dimethylcyclopropane-1,1-dicarboxylic acid methyl ester 在 盐酸 、 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 1.5h， 生成 1-氨基-2,2-二甲基环丙烷羧酸
  参考文献：
  名称：

  Straightforward Synthesis of 1-Amino-2,2-dialkylcyclopropanecarboxylic Acids via Selective Saponification of 2,2-Dialkylcyclopropane-1,1-dicarboxylic Esters and Curtius Rearrangement

  摘要：

  Selective monosaponification of dimethyl 2,2-dialkylcyclopropane-1,1l-dicarboxylic esters afforded the corresponding 2,2-dialkyl-1-(methoxycarbonyl)cyclopropane-1-carboxylic acids, which were rearranged with diphenyl phosphoroazidate via a modified Curtius-type reaction to give methyl 2,2-dialkyl-1-[N-(alkoxycarbonyl)amino]cyclopropanecarboxylic esters. Selective deprotection of the carbamate or methyl cyclopropanecarboxylic ester was worked out, giving rise to a whole variety of ACC analogues. Straightforward ways to 1-amino-2,2-dialkylcyclopropanecarboxylic acids (2,2-dialkyl-ACC's) were developed.

  DOI：

  10.1021/jo00105a045
• 作为产物：
  描述：

  dimethyl 2,2-dimethyl-cyclopropane-1,1-dicarboxylate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以86%的产率得到2,2-dimethylcyclopropane-1,1-dicarboxylic acid methyl ester
  参考文献：
  名称：

  Straightforward Synthesis of 1-Amino-2,2-dialkylcyclopropanecarboxylic Acids via Selective Saponification of 2,2-Dialkylcyclopropane-1,1-dicarboxylic Esters and Curtius Rearrangement

  摘要：

  Selective monosaponification of dimethyl 2,2-dialkylcyclopropane-1,1l-dicarboxylic esters afforded the corresponding 2,2-dialkyl-1-(methoxycarbonyl)cyclopropane-1-carboxylic acids, which were rearranged with diphenyl phosphoroazidate via a modified Curtius-type reaction to give methyl 2,2-dialkyl-1-[N-(alkoxycarbonyl)amino]cyclopropanecarboxylic esters. Selective deprotection of the carbamate or methyl cyclopropanecarboxylic ester was worked out, giving rise to a whole variety of ACC analogues. Straightforward ways to 1-amino-2,2-dialkylcyclopropanecarboxylic acids (2,2-dialkyl-ACC's) were developed.

  DOI：

  10.1021/jo00105a045

文献信息

• Hemisynthesis of methyl pyrethroates from γ-alkoxy-alkylidene malonates and isopropylidenediphenylsulfurane and isopropylidenetriphenylphosphorane
  作者：Alain Krief、Alexandre Froidbise

  DOI：10.1016/j.tet.2004.06.035

  日期：2004.8

  Hemi synthesis of methyl pyrethroates from gamma-alkoxy-alkylidene malonates and isopropylidenediphenylsulfurane and isopropylidenetriphenylphosphorane is disclosed. It takes advantage of the high degree of stereocontrol observed in the cyclopropanation of gamma-alkoxy-alkylidene malonates by the above mentioned ylides. (C) 2004 Elsevier Ltd. All rights reserved.
• De Kimpe Norbert, Boeykens Marc, Tehrani Kourosch Abbaspour, J. Org. Chem, 59 (1994) N 26, S 8215-8219
  作者：De Kimpe Norbert, Boeykens Marc, Tehrani Kourosch Abbaspour

  DOI：——

  日期：——