diethyl 2-propylcyclopropane-1,1-dicarboxylate | 18795-94-3

• 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
• 英文名称: diethyl 2-propylcyclopropane-1,1-dicarboxylate
• 英文别名: 2-n-Propyl-cyclopropan-1.1-dicarbonsaeure-diethylester
• CAS: 18795-94-3
• 化学式: C₁₂H₂₀O₄
• 分子量: 228.288
• InChiKey: FFUSAWHMLZTBMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  diethyl 2-propylcyclopropane-1,1-dicarboxylate 在 水 、 sodium hydroxide 、 potassium hydrogensulfate 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以88%的产率得到1-(ethoxycarbonyl)-2-propylcyclopropanecarboxylic acid
  参考文献：
  名称：

  Synthesis and anticonvulsant activity of new 6-methyl-1-substituted-4,6-diazaspiro[2.4]heptane-5,7-diones

  摘要：

  In the present study on the development of new anticonvulsants, twenty new 6-methyl-1-substituted-4,6-diazaspiro[2.4]heptane-5,7-diones were synthesized and tested for anticonvulsant activity using the maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) screens. Their neurotoxicity was determined by the rotorod test. In this series, all of the alkyl- and aryl-substituted 5,5-cyclo-propanespirohydantoins showed more or less protection against MES and/or scPTZ models. The most active of the series was 6-methyl-1-(4-(methylsulfonyl)phenyl)-4,6-diazaspiro[2.4]heptane-5,7-dione (6t), which showed a MES ED50 value of 12.5 mg/kg in mice. The median toxic dose (TD50) was 310 mg/kg, providing compound 6t with a protection index (PI = TD50/ED50) of 24.8 in the MES test which is better than phenytoin. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.034
• 作为产物：
  描述：

  4-propyl-4,5-dihydro-pyrazole-3,3-dicarboxylic acid diethyl ester 以 xylene 为溶剂， 生成 diethyl 2-propylcyclopropane-1,1-dicarboxylate
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• Latent inhibitors. Part 7. Inhibition of dihydro-orotate dehydrogenase by spirocyclopropanobarbiturates
  作者：William Fraser、Colin J. Suckling、Hamish C. S. Wood

  DOI：10.1039/p19900003137

  日期：——

  synthesized. Dihydro-orotate dehydrogenase from Clostridium oroticum was shown to be inhibited by these compounds. A related series of 5-membered-ring compounds (hydantoins and pyrazoles) was prepared but all the compounds were found to be inactive. In order to correlate these observations with previous results concerning 5-arylmethylhydantoins and 5-arylidene-hydantoins as inhibitors, 5-arylidenebarbiturates

  合成了一系列在环丙烷环上带有烷基和芳基取代基的5-螺环丙烷基巴比妥酸酯。已证明来自Orticum的梭状芽孢杆菌的二氢乳清酸脱氢酶被这些化合物抑制。制备了一系列相关的五元环化合物（乙内酰脲和吡唑），但发现所有化合物均无活性。为了使这些观察结果与以前的有关5-芳基甲基乙内酰脲和5-芳基-乙内酰脲作为抑制剂的结果相关联，还评估了5-芳基戊二酸酯作为抑制剂，发现它们是所研究化合物中活性最高的。该结果在该酶的分子识别的背景下以及使用底物替代物作为构建酶潜在抑制剂的模板的背景下得到了解释。
• Temperature Tunable Synthesis of Tetrahydro-4<i>H</i>-pyrrolo[3,2-<i>c</i>]quinolin-4-ones and Dihydro-1<i>H</i>-benzo[<i>b</i>]azepines from 2-Aminobenzonitriles and Donor–Acceptor Cyclopropanes
  作者：Bikoshita Porashar、Subhamoy Biswas、Archana Kumari Sahu、Archana Chutia、Anil K. Saikia

  DOI：10.1021/acs.orglett.2c03674

  日期：2022.12.16

  mediated by SnCl4 in moderate to good yields. The reaction involves the initial ring opening of a cyclopropane ring due to activation by SnCl4 followed by nucleophilic attack by amine to give an adduct, which after unprecedented rearrangement at two different reaction temperatures provides two nitrogen heterocyclic compounds. This methodology can be used for the synthesis of hexahydropyrrolo[3,2-c]quinolinone

  Tetrahydro-4 H -pyrrolo[3,2- c ]quinolin-4-ones 和 dihydro-1 H -benzo [ b ]azepines 是由 SnCl 4介导的 2-氨基苯甲腈和供体-受体环丙烷以中等到良好的收率有效合成的. 该反应包括由于 SnCl 4的活化而导致环丙烷环的初始开环，然后是胺的亲核攻击以产生加合物，该加合物在两个不同的反应温度下进行前所未有的重排后提供两种氮杂环化合物。该方法可用于合成六氢吡咯并 [3,2- c ] 喹啉酮衍生物，其结构存在于生物活性分子中。
• 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：——
• Synthesis and anticonvulsant activity of new 6-methyl-1-substituted-4,6-diazaspiro[2.4]heptane-5,7-diones
  作者：Xianran He、Guanpeng Qiu、Jin Yang、Yuling Xiao、Zhongyuan Wu、Guofu Qiu、Xianming Hu

  DOI：10.1016/j.ejmech.2010.05.034

  日期：2010.9

  In the present study on the development of new anticonvulsants, twenty new 6-methyl-1-substituted-4,6-diazaspiro[2.4]heptane-5,7-diones were synthesized and tested for anticonvulsant activity using the maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) screens. Their neurotoxicity was determined by the rotorod test. In this series, all of the alkyl- and aryl-substituted 5,5-cyclo-propanespirohydantoins showed more or less protection against MES and/or scPTZ models. The most active of the series was 6-methyl-1-(4-(methylsulfonyl)phenyl)-4,6-diazaspiro[2.4]heptane-5,7-dione (6t), which showed a MES ED50 value of 12.5 mg/kg in mice. The median toxic dose (TD50) was 310 mg/kg, providing compound 6t with a protection index (PI = TD50/ED50) of 24.8 in the MES test which is better than phenytoin. (C) 2010 Elsevier Masson SAS. All rights reserved.