diethyl 2-(furan-2-yl)cyclopropane-1,1-dicarboxylate | 72174-96-0

• 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-(furan-2-yl)cyclopropane-1,1-dicarboxylate
• 英文别名: diethyl 2-(furan)cyclopropane-1,1-dicarboxylate；diethyl 2-furanyl-1,1-cyclopropanedicarboxylate
• CAS: 72174-96-0
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: RWFQCLZFUUDHQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 2-(furan-2-yl)cyclopropane-1,1-dicarboxylate 在 水 、 sodium hydroxide 、 potassium hydrogensulfate 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以86%的产率得到1-(ethoxycarbonyl)-2-(furan-2-yl)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：

  糠醛 在 正丁基锂 、 硫酸 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 3.5h， 生成 diethyl 2-(furan-2-yl)cyclopropane-1,1-dicarboxylate
  参考文献：
  名称：

  S-Ethenylsulfoximine derivatives. Reagents for ethylenation of protic nucleophiles

  摘要：

  DOI：

  10.1021/jo01290a012

文献信息

• Ring Opening of Donor-Acceptor Cyclopropanes with the Azide Ion: A Tool for Construction of N-Heterocycles
  作者：Konstantin L. Ivanov、Elena V. Villemson、Ekaterina M. Budynina、Olga A. Ivanova、Igor V. Trushkov、Mikhail Ya. Melnikov

  DOI：10.1002/chem.201405551

  日期：2015.3.23

  general method for ring opening of various donor–acceptor cyclopropanes with the azide ion through an SN2‐like reaction has been developed. This highly regioselective and stereospecific process proceeds through nucleophilic attack on the more‐substituted C2 atom of a cyclopropane with complete inversion of configuration at this center. Results of DFT calculations support the SN2 mechanism and demonstrate

  已经开发出一种通用的方法，可通过类似S N 2的反应，将叠氮离子与各种供体-受体环丙烷开环。这种高度区域选择性和立体选择性的过程是通过亲核攻击环丙烷的更取代的C2原子进行的，该中心的构型完全反转。DFT计算结果支持S N2机理，证明环丙烷的相对实验反应性与计算出的能垒之间具有良好的定性相关性。该反应为多种多官能叠氮化物提供了一种简单的方法，产率高达91％。这些叠氮化物具有很高的合成效用，并参与了面向多样性的合成，这是通过已开发的将其转变为五元，六元和七元N杂环以及复杂的环状化合物的多径策略证明的。包括天然产物和药物，如（-）-尼古丁和阿托伐他汀。
• Copper-Catalyzed Oxidative Dehydrogenative Reaction of Quinoline-<i>N</i>-Oxides with Donor–Acceptor Cyclopropanes: Installation of a Tertiary Alkyl Motif at C2 Position
  作者：Bikash Kumar Sarmah、Monuranjan Konwar、Animesh Das

  DOI：10.1021/acs.orglett.1c03115

  日期：2021.11.5

  A copper-catalyzed oxidative dehydrogenative reaction of quinoline N-oxides with donor–acceptor cyclopropanes has been demonstrated to construct C2-alkylated quinolines containing a γ-keto diester motif. The use of molecular oxygen as an oxidant, excellent site-selectivity, and good functional group tolerance are the important features in this process. The preliminary mechanistic studies demonstrate

  喹啉N-氧化物与供体-受体环丙烷的铜催化氧化脱氢反应已被证明可以构建含有γ-酮二酯基序的C2-烷基化喹啉。使用分子氧作为氧化剂，优异的位点选择性和良好的官能团耐受性是该过程的重要特征。初步机理研究表明，该催化剂具有作为路易斯酸和氧化还原催化剂的双重作用。
• Lewis Acid-Catalyzed [3+2] Cycloaddition of Donor-Acceptor Cyclopropanes and Enamines: Enantioselective Synthesis of Nitrogen-Functionalized Cyclopentane Derivatives
  作者：Kamal Verma、Prabal Banerjee

  DOI：10.1002/adsc.201600221

  日期：2016.6.30

  efficient method for the synthesis of nitrogen‐functionalized cyclopentane derivatives via [3+2] cycloaddition of enamines with donor‐acceptor cyclopropanes in the presence of catalytic amounts of various Lewis acids at room temperature has been developed; furthermore, the corresponding β‐amino acid was synthesized by monodecarboxylation and hydrogenolysis. An enantioenriched synthesis of nitrogen‐functionalized

  在室温下催化量的各种路易斯酸存在下，开发了一种简单有效的方法，可通过烯胺与供体-受体环丙烷的[3 + 2]环加成反应，合成氮官能化的环戊烷衍生物；此外，通过单脱羧和氢解合成了相应的β-氨基酸。通过外消旋给体-受体环丙烷的动态动力学不对称转化，对氮官能化的环戊烷衍生物进行了对映体富集合成，采用铜络合物[Cu（OTf）2 - L1 ]作为催化剂，对映体比例高达8：1。
• Reaction of donor-acceptor cyclopropanes with 1,3-diphenylisobenzofuran. Lewis acid effect on the reaction pathway
  作者：A. O. Chagarovskiy、O. A. Ivanova、E. M. Budynina、E. L. Kolychev、M. S. Nechaev、I. V. Trushkov、M. Ya. Mel’nikov

  DOI：10.1007/s11172-013-0349-x

  日期：2013.11

  Sn(OTf)2, SnCl2, ZnCl2, GaCl3, and MgI2, proceeds as a formal [3+4]-cycloaddition leading to a newly formed seven-membered ring. This reaction was found to be typical of cyclopropane-1,1-diesters and dinitriles, as well as 1-nitrocyclo-propanecarboxylates containing aromatic, heteroaromatic, and vinylic substituents at the C(2) atom of the small ring. When Me3SiOTf, TiCl4, SnCl4, or BF3·OEt2 were used as initiators

  在镧系元素三氟甲磺酸盐以及 CuOTf、Sn(OTf)2、SnCl2、ZnCl2、GaCl3 和 MgI2 存在下，供体-受体环丙烷与 1,3-二苯基异苯并呋喃的反应以正式的 [3+4]-环加成形式进行导致新形成的七元环。发现该反应是典型的环丙烷-1,1-二酯和二腈，以及在小环的 C(2) 原子上含有芳族、杂芳族和乙烯基取代基的 1-硝基环丙烷羧酸酯。当 Me3SiOTf、TiCl4、SnCl4 或 BF3·OEt2 用作引发剂时，通过环丙烷和亲核试剂与二烯部分的共轭 1,4-加成形成了不寻常的环状半缩醛。
• Lewis Acid Catalyzed Annulation of Cyclopropane Carbaldehydes and Aryl Hydrazines: Construction of Tetrahydropyridazines and Application Toward a One-Pot Synthesis of Hexahydropyrrolo[1,2-<i>b</i>]pyridazines
  作者：Raghunath Dey、Pankaj Kumar、Prabal Banerjee

  DOI：10.1021/acs.joc.8b00332

  日期：2018.5.18

  In this report, a facile synthesis of tetrahydropyridazines via a Lewis acid catalyzed annulation reaction of cyclopropane carbaldehydes and aryl hydrazines has been demonstrated. Moreover, the generated tetrahydropyridazine further participated in a cycloaddition reaction with donor–acceptor cyclopropanes to furnish hexahydropyrrolo[1,2-b]pyridazines. We also performed these two steps in one pot in

  在该报告中，已经证明了通过路易斯酸催化的环丙烷甲醛和芳基肼的环合反应可轻松合成四氢哒嗪。此外，生成的四氢哒嗪进一步与供体-受体环丙烷一起参与环加成反应，提供六氢吡咯并[1,2- b ]哒嗪。我们还在一个锅中以连续的方式执行了这两个步骤。另外，六氢吡咯并[1,2- b ]哒嗪的单脱羧反应得到了良好的收率。