Dimethyl 2,2-diethylcyclopropane-1,1-dicarboxylic ester | 68157-21-1

• 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-diethylcyclopropane-1,1-dicarboxylic ester
• 英文别名: dimethyl 2,2-diethylcyclopropane-1,1-dicarboxylate；1,1-Diethyl-2,2-dimethoxycarbonylcyclopropan
• CAS: 68157-21-1
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: ZKUCECMXRFGVEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Dimethyl 2,2-diethylcyclopropane-1,1-dicarboxylic ester 在 sodium hydroxide 、 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 甲醇 、 苯 为溶剂， 反应 26.0h， 生成 Methyl 2,2-diethyl-1-isocyanatocyclopropane-1-carboxylate
  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-bromo-2-ethylbutylidene)propanedioate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 Dimethyl 2,2-diethylcyclopropane-1,1-dicarboxylic ester
  参考文献：
  名称：

  Preparation of 2,2-Dialkylcyclopropanes Geminally Substituted with Electron-Withdrawing Groups

  摘要：

  DOI：

  10.1055/s-1978-24799

文献信息

• Peptide-Based Inhibitors of the Hepatitis C Virus NS3 Protease:  Structure−Activity Relationship at the <i>C</i>-Terminal Position
  作者：Jean Rancourt、Dale R. Cameron、Vida Gorys、Daniel Lamarre、Martin Poirier、Diane Thibeault、Montse Llinàs-Brunet

  DOI：10.1021/jm030573x

  日期：2004.5.1

  position of a tetrapeptide such as 1 led to a significant gain in the inhibitory enzymatic activity, as compared to the corresponding norvaline derivative 2, prompted a systematic study of substituent effects on the three-membered ring. We report herein that the incorporation of a vinyl group with the proper configuration onto this small cycle produced inhibitors of the protease with much improved in vitro

  呈现了丙型肝炎病毒NS3蛋白酶的基于肽的抑制剂的C末端位置的结构活性关系。先前已经描述了观察到源自NS5A / 5B切割位点的底物的N-末端切割产物（DDIVPC-OH）是NS3蛋白酶的竞争性抑制剂。在这些基于肽的抑制剂的P1位置发现的化学上不稳定的半胱氨酸残基可以用正缬氨酸残基代替，但会大大降低酶的活性。与相应的正缬氨酸衍生物2相比，四肽P1位（例如1）的氨基环丙烷羧酸（ACCA）残基导致抑制酶活性的显着提高，这一事实促使系统地研究了取代基对甲壳素的影响。三元环。我们在本文中报道，将具有适当构型的乙烯基掺入该小循环中产生了蛋白酶抑制剂，其体外效力大大提高。乙烯基-ACCA是第一个报道的含有P1残基的羧酸，该羧酸可产生NS3蛋白酶抑制剂，其活性远高于在相同位置上含有半胱氨酸的抑制剂。
• A novel method for the sterically shielded pyrrolidine nitroxides synthesis using donor–acceptor cyclopropanes
  作者：Andrey I. Taratayko、Sophia Yu. Trakhinina、Konstantin A. Lomanovich、Igor A. Kirilyuk

  DOI：10.1016/j.tetlet.2023.154546

  日期：2023.6

  shielded nitroxides were shown to demonstrate resistance to bioreduction. For this reason, they are attracting much interest as spin labels and probes for in-cell and in vivo EPR and NMR applications. Formal [3 + 2] cycloaddition reaction of donor–acceptor cyclopropanes with propionitrile provided 1-pyrrolines which were converted to the new sterically shielded achiral pyrrolidine nitroxides via several

  空间屏蔽的氮氧化合物显示出对生物还原的抗性。出于这个原因，它们作为细胞内和体内 EPR 和NMR应用的自旋标记物和探针引起了人们的极大兴趣。供体-受体环丙烷与丙腈的正式 [3 + 2] 环加成反应提供 1-吡咯啉，通过几个步骤将其转化为新的空间屏蔽非手性吡咯烷氮氧化物。
• VERHE R.; DE KIMPE N.; DE BUYCK L.; COURTHEYN D.; SCHAMP N., SYNTHESIS, 1978, NO 7, 530-532
  作者：VERHE R.、 DE KIMPE N.、 DE BUYCK L.、 COURTHEYN D.、 SCHAMP N.

  DOI：——

  日期：——
• 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.
• 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：——