甲基1-氨基-2,2-二甲基环丙烷羧酸酯 | 159279-77-3

• 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
• 中文名称: 甲基1-氨基-2,2-二甲基环丙烷羧酸酯
• 英文名称: Methyl 1-amino-2,2-dimethylcyclopropanecarboxylic ester
• 英文别名: Methyl 1-amino-2,2-dimethylcyclopropane-1-carboxylate
• CAS: 159279-77-3
• 化学式: C₇H₁₃NO₂
• mdl: MFCD03426285
• 分子量: 143.186
• InChiKey: GQIMUGKTLQYUKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.857
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,2-Dimethyl-3-oxo-1-butyl trifluoroacetate 在 吡啶 、 磺酰氯 、 溴 、 sodium methylate 、 草酸 、 四氯化钛 、 碳酸氢钠 、 对甲苯磺酸 、 silver carbonate 、 lithium chloride 作用下， 以 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 91.08h， 生成 甲基1-氨基-2,2-二甲基环丙烷羧酸酯
  参考文献：
  名称：

  Synthesis of 1-Amino-2,2-dialkylcyclopropanecarboxylic Acids via Base-Induced Cyclization of .gamma.-Chloro-.alpha.-imino Esters

  摘要：

  beta-Chloro ketones were oxidatively transformed into alpha-keto carboxylic esters and condensed with primary amines in the presence of titanium(IV) chloride. Base-induced cyclization of the resulting gamma-chloro-alpha-imino esters, incorporating suitable N-substituents, led directly to 1-amino-2,2-dialkyl- cyclopropanecarboxylic ester derivatives via a 1,5-dehydrochlorination process. Syntheses of different N- and/or carboxyl-protected geminally (gem) dialkylated cyclopropane amino acids were developed, while access to the free alpha-amino acids is also given. The methodology used was further extended by reduction of the gamma-chloro-alpha-imino esters to functionalized gamma-chloro-alpha-amino esters,prior to ring closure, affording N-alkyl-gem-dialkyl-1-aminocyclopropanecarboxylic acid derivatives.

  DOI：

  10.1021/jo00102a022

文献信息

• Straightforward Synthesis of 1-Amino-2,2-dialkylcyclopropanecarboxylic Acids via Selective Saponification of 2,2-Dialkylcyclopropane-1,1-dicarboxylic Esters and Curtius Rearrangement
  作者：Norbert De Kimpe、Marc Boeykens、Kourosch Abbaspour Tehrani

  DOI：10.1021/jo00105a045

  日期：1994.12

  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.
• 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：——
• Boeykens Marc, De Kimpe Norbert, Tehrani Kourosch Abbaspour, J. Org. Chem, 59 (1994) N 23, S 6973-6985
  作者：Boeykens Marc, De Kimpe Norbert, Tehrani Kourosch Abbaspour

  DOI：——

  日期：——
• SUBSTITUTED QUINAZOLINES
  申请人：Franklin Richard

  公开号：US20080176875A1

  公开（公告）日：2008-07-24

  This invention relates to the discovery of prodrugs of 3- or 5-substituted analogues of the selective platelet lowering agent anagrelide which have reduced potential for cardiovascular side-effects and which should therefore lead to improved patient compliance and safety in the treatment of myeloproliferative diseases. More specifically, the present invention relates to prodrugs of certain imidazoquinazoline derivatives which have utility as platelet lowering agents in humans. The compounds of the present invention function by inhibiting the formation of blood platelets.
• US8304420B2
  申请人：——

  公开号：US8304420B2

  公开（公告）日：2012-11-06