Diethyl 2-butylcyclopropane-1,1-dicarboxylate | 72435-01-9

• 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-butylcyclopropane-1,1-dicarboxylate
• 英文别名: diethyl-2-butylcyclopropane-1,1-dicarboxylate；1,1-diethoxycarbonyl-2-butylcyclopropane
• CAS: 72435-01-9
• 化学式: C₁₃H₂₂O₄
• 分子量: 242.315
• InChiKey: CTFBTZISAUIDPO-UHFFFAOYSA-N

物化性质

• 沸点：
  69-70 °C(Press: 0.08 Torr)
• 密度：
  1.051±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 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-butylcyclopropane-1,1-dicarboxylate 在 水 、 sodium hydroxide 、 potassium hydrogensulfate 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以82%的产率得到2-butyl-1-(ethoxycarbonyl)cyclopropanecarboxylic 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：

  diethyl 2-(4-hydroxybutyl)cyclopropane-1,1-dicarboxylate 在 咪唑 、 碘 、 三苯基膦 、 fac-tris(2-phenylpyridinato-N,C2')iridium(III) 、 N,N-二异丙基乙胺 作用下， 以 乙腈 、 甲醇 为溶剂， 反应 0.3h， 以87%的产率得到Diethyl 2-butylcyclopropane-1,1-dicarboxylate
  参考文献：
  名称：

  使用可见光光氧化还原催化间歇流脱氧。

  摘要：

  本文中，我们报告了通过Garegg-Samuelsson反应，可见光-光氧化还原催化和流化法相结合开发的伯醇和仲醇的一锅脱氧方案。该方法的特点是反应条件温和，反应物和试剂易于处理，对官能团的耐受性强，产率高。

  DOI：

  10.1039/c2cc37206a

文献信息

• Single electron transfer induced elemental steps in the transformation of iodomalonic esters and related CH-acids under solid-liquid PTC conditions. Preparation of electrophilic cyclopropanes
  作者：László Tőke、Zoltán Hell、Gábor T. Szabó、Gábor Tóth、Mária Bihari、Antal Rockenbauer

  DOI：10.1016/s0040-4020(01)81878-0

  日期：1993.6.4

  Single electron transfer induced elemental steps have been shown to occur during the transformation of iodomalonic esters and related CH-acids to cyclopropane derivatives under solid-liquid phase transfer catalytic conditions. The iodo derivatives are formed from iodine and CH-acids “in situ”, in the same pot in which the transformations to cyclopropane derivatives take place. A number of electrophilic

  已显示在固液相转移催化条件下，碘化丙二酸酯和相关的CH-酸向环丙烷衍生物的转化过程中，发生单电子转移诱导的元素步骤。碘衍生物是由碘和CH酸“原位”形成的，在同一锅中发生向环丙烷衍生物的转化。通过这种途径已经合成了许多具有广泛取代基的亲电子环丙烷。
• 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。
• Reaction of non-activated olefins with CH-acids; a novel method for the preparation of electrophilic cyclopropanes
  作者：László Tóke、Gábor T Szabó、Zoltán Hell、Gábor Tóth

  DOI：10.1016/s0040-4039(00)88529-9

  日期：1990.1

  Reaction of non-activated olefines with active methylene compounds was accomplished under solid-liquid phase-transfer conditions, in the presence of iodine, to give electrophilic cyclopropanes of a wide range of substituents. Several data to the mechanism of the reaction are also given.

  非活化烯烃与活性亚甲基化合物的反应是在碘存在下在固-液相转移条件下完成的，得到了​​具有广泛取代基的亲电子环丙烷。还给出了反应机理的一些数据。
• Oxidative addition of 1,3-dicarbonyl compounds to olefins by the action of the Mn(OAc)3/LiCl system and the synthesis of functionally substituted cyclopropanes
  作者：M. G. Vinogradov、V. I. Dolinko、G. I. Nikishin

  DOI：10.1007/bf00951066

  日期：1984.2
• Electrosynthesis of cyclopropane derivatives by a Perkin-type reaction
  作者：V. A. Petrosyan、A. A. Vasil'ev、V. I. Tatarinova

  DOI：10.1007/bf00699141

  日期：1994.1

  Electrolysis of active methylene compounds at a Pt cathode in MeCN in the presence of vicinal dihaloalkanes leads to cyclopropane derivatives in yields up to 90 %. In the cases of CH-acids with low pK(a) it is expedient to apply more active dihaloalkanes, while for CH-acids with higher pK(a) the desired product yields may be raised using electrogenerated bases.