dimethyl 2,2-dimethyl-cyclopropane-1,1-dicarboxylate | 18795-95-4

• 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: dimethyl 2,2-dimethyl-cyclopropane-1,1-dicarboxylate
• 英文别名: 1,1-Cyclopropanedicarboxylic acid, 2,2-dimethyl-, dimethyl ester；dimethyl 2,2-dimethylcyclopropane-1,1-dicarboxylate
• CAS: 18795-95-4
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: XZAFBFQLKXHZTO-UHFFFAOYSA-N

物化性质

• 熔点：
  49-52 °C
• 沸点：
  95 °C(Press: 15 Torr)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl 2,2-dimethyl-cyclopropane-1,1-dicarboxylate 在 盐酸 、 sodium hydroxide 、 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 16.5h， 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-bromo-2-methylpropylidenemalonate 在 sodium tetrahydroborate 作用下， 生成 dimethyl 2,2-dimethyl-cyclopropane-1,1-dicarboxylate
  参考文献：
  名称：

  Verhe,R. et al., Bulletin des Societes Chimiques Belges, 1977, vol. 86, p. 55 - 63

  摘要：

  DOI：

文献信息

• Synthesis of five-membered cyclic nitrones based on the Lewis acid-catalysed [3+2]-annulation reaction of donor–acceptor cyclopropanes with 1,4,2-dioxazoles
  作者：Zhe-Hao Wang、Huan-Huan Zhang、Peng-Fei Xu、Yong-Chun Luo

  DOI：10.1039/c8cc04656e

  日期：——

  A novel synthesis of five-membered cyclic nitrones has been developed based on the Lewis acid-catalysed [3+2]-annulation reaction of D–A cyclopropanes with 1,4,2-dioxazoles. Broad substrate scope and generally good yield make this reaction useful in the preparation of nitrones. When a suitable 1,4,2-dioxazole was used, nitrone and tetrahydrofuran could be prepared in one pot with high atom economy

  基于路易斯酸催化D–A环丙烷与1,4,2-二恶唑的[3 + 2]环化反应，开发了五元环硝酮的新型合成方法。广泛的底物范围和通常良好的产率使该反应可用于制备硝酮。当使用合适的1,4,2-二恶唑时，可以在一个具有高原子经济性的锅中制备硝酮和四氢呋喃。
• Cobalt Porphyrin Catalyzed [3+2] Cycloaddition of Cyclopropanes and Carbonyl Compounds
  作者：Takuya Kurahashi、Seijiro Matsubara、Takahiro Shiba、Daiki Kuroda

  DOI：10.1055/s-0034-1378394

  日期：——

  A cobalt porphyrin efficiently catalyzed the formal [3+2] cycloaddition of alkyl-/aryl-substituted cyclopropanes and carbonyl compounds such as aldehydes and ketones to afford the corresponding substituted tetrahydrofurans. The use of the cobalt porphyrin complex as a Lewis acid to catalyze the reaction via the electrophilic activation of cyclopropanes was demonstrated. The high functional-group tolerance

  钴卟啉有效地催化烷基-/芳基-取代的环丙烷和羰基化合物（如醛和酮）的正式[3+2]环加成反应，得到相应的取代四氢呋喃。证明了使用钴卟啉配合物作为路易斯酸通过环丙烷的亲电活化来催化反应。还证明了催化剂的高官能团耐受性和稳健性。此外，通过进行环酮和环丙烷的环加成反应得到螺四氢呋喃，证明了该催化剂的潜在效用。
• S-Ethenylsulfoximine derivatives. Reagents for ethylenation of protic nucleophiles
  作者：Carl R. Johnson、James P. Lockard、Eugene R. Kennedy

  DOI：10.1021/jo01290a012

  日期：1980.1
• Danion-Bougot,R.; Carrie,R., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1968, vol. 266, p. 645 - 648
  作者：Danion-Bougot,R.、Carrie,R.

  DOI：——

  日期：——
• Preparation of 2,2-Dialkylcyclopropanes Geminally Substituted with Electron-Withdrawing Groups
  作者：Roland VERHÉ、Norbert DE KIMPE、Laurent DE BUYCK、Dirk COURTHEYN、Niceas SCHAMP

  DOI：10.1055/s-1978-24799

  日期：——