diethyl 2-(4-(dimethylamino)phenyl)cyclopropane-1,1-dicarboxylate | 77094-95-2

• 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-(4-(dimethylamino)phenyl)cyclopropane-1,1-dicarboxylate
• 英文别名: Diethyl 2-[4-(dimethylamino)phenyl]cyclopropane-1,1-dicarboxylate
• CAS: 77094-95-2
• 化学式: C₁₇H₂₃NO₄
• 分子量: 305.374
• InChiKey: QDGHMGXTOMSWMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 2-(4-(dimethylamino)phenyl)cyclopropane-1,1-dicarboxylate 在 四氯化锡 作用下， 以 硝基甲烷 为溶剂， 反应 3.0h， 以86%的产率得到(2RS,5RS)-tetraethyl 2,5-bis[4-(dimethylamino)phenyl]cyclohexane-1,1,4,4-tetracarboxylate
  参考文献：
  名称：

  (3 + 3)-Cyclodimerization of Donor–Acceptor Cyclopropanes. Three Routes to Six-Membered Rings

  摘要：

  The ability of donor acceptor cyclopropanes to (3 + 3)-cyclodimerize is disclosed. It has been found that Lewis acid-induced transformations of 2-(hetero)arylcyclopropane-1,1-dicarboxylates containing electron-abundant aromatic substituents led to the construction of six-membered cyclic systems. Depending on the substrate properties and the Lewis acid applied, three types of products can be obtained: (1) 1,4-diarylcyclohexanes, (2) 1-aryl-1,2,3,4-tetrahydronaphthalenes, and (3) 9,10-dihydroanthracenes.

  DOI：

  10.1021/jo201612w
• 作为产物：
  描述：

  diethyl p-(N,N'-dimethylamino)-benzylidenemalonate 、 三甲基碘化亚砜 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 2.2h， 生成 diethyl 2-(4-(dimethylamino)phenyl)cyclopropane-1,1-dicarboxylate
  参考文献：
  名称：

  MgI2促进的[2 + 4]环加成反应从原位生成的2-苯乙烯基丙二酸酯的供体-受体环丙烷和邻苯二甲酰亚胺合成茚并吡啶衍生物。

  摘要：

  已经开发出了出乎意料的MgI 2促进的[2 + 4]环加成反应，该反应是在温和的反应条件下，从供体-受体环丙烷中与硫属元素胺生成2-苯乙烯基丙二酸酯，合成高取代度茚并吡啶衍生物。此外，这些衍生物还用于通过氧化C = C键裂解和Meinwald型重排生成螺[氧代茚满-吡咯烷]衍生物来合成高度取代的9元内酰胺。

  DOI：

  10.1002/adsc.201800598

文献信息

• Lewis Acid-Catalyzed Isomerization of 2-Arylcyclopropane-1,1-dicarboxylates: A New Efficient Route to 2-Styrylmalonates
  作者：Alexey O. Chagarovskiy、Olga A. Ivanova、Eduard R. Rakhmankulov、Ekaterina M. Budynina、Igor V. Trushkov、Mikhail Ya. Melnikov

  DOI：10.1002/adsc.201000636

  日期：2010.12.17

  A facile efficient approach to the 2-styrylmalonates via the Lewis acid-catalyzed isomerization of 2-arylcyclopropane-1,1-dicarboxylates has been developed. The efficiency of this method was demonstrated for a representative series of such cyclopropanes. The isomerization proceeds chemo-, regio- and stereoselectively to afford E-styrylmalonates in good yields.

  已经开发了通过路易斯酸催化的2-芳基环丙烷-1，1-二羧酸酯异构化2-苯乙烯基丙二酸酯的简便有效方法。对于代表性的此类环丙烷系列，证明了该方法的效率。异构化进行化学，区域和立体选择性，以高收率得到E-苯乙烯基丙二酸酯。
• [3+3] Annulation via Ring Opening/Cyclization of Donor-Acceptor Cyclopropanes with (Un)symmetrical Ureas: A Quick Access to Highly Functionalized Tetrahydropyrimidinones
  作者：Irshad Maajid Taily、Debarshi Saha、Prabal Banerjee

  DOI：10.1002/ejoc.201901400

  日期：2019.12.31

  straight‐forward access to pharmacologically privileged tetrahydropyrimidinones exploiting readily available Donor–Acceptor cyclopropanes (DACs) is reported. This methodology involves the Lewis acid catalyzed synthesis of uriedo‐malonates from (un)symmetrical and unsymmetrical ureas and DACs followed by I2‐base mediated cyclization to form their corresponding tetrahydropyrimidinones in moderate to excellent

  据报道，利用现成的供体-受体环丙烷（DACs），可以轻松，直接地获得具有药理学优势的四氢嘧啶酮。该方法涉及路易斯酸催化（不对称和不对称尿素和DACs合成尿酸-丙二酸酯），然后由I 2碱介导的环化反应，以中等至优异的产率形成相应的四氢嘧啶酮。
• Lewis Acid-Catalyzed [3+3] Annulation of Donor–Acceptor Cyclopropanes and Indonyl Alcohols: One Step Synthesis of Substituted Carbazoles with Promising Photophysical Properties
  作者：Rohit Kumar Varshnaya、Prabal Banerjee

  DOI：10.1021/acs.joc.8b02733

  日期：2019.2.1

  protocol to access carbazole from donor–acceptor cyclopropane and indonyl alcohol via [3+3] annulation in the presence of a Lewis acid has been demonstrated. This method facilitates the post functionalization of the substituted carbazole into a fully conjugated π-system exhibiting intense emission bands in the visible range of the spectrum and also offers a convenient route toward the synthesis of pityriazole

  在路易斯酸存在下，通过[3 + 3]环化从供体-受体环丙烷和茚满醇中获取咔唑的高效方法已得到证明。该方法有助于将取代的咔唑后官能化为完全共轭的π系统，该π系统在光谱的可见光范围内显示出很强的发射带，并且还为合成pityriazole衍生物提供了一条便利的途径。
• Switchable Reactivity of Cyclopropane Diesters toward (3 + 3) and (3 + 2) Cycloadditions with Benzoquinone Esters
  作者：Navpreet Kaur、Pankaj Kumar、Arijit Hazra、Prabal Banerjee

  DOI：10.1021/acs.orglett.2c03446

  日期：2022.11.11

  Herein, we describe an unprecedented (3 + 3) cycloaddition reaction of the donor–acceptor cyclopropanes with quinone esters toward the construction of chroman scaffolds in moderate to good yields. Interestingly, the strategy is also adjustable toward a (3 + 2) cycloaddition by just switching the Lewis acid to furnish benzofuran scaffolds. Based on the choice of Lewis acid used, the same set of precursors

  在此，我们描述了一种前所未有的供体-受体环丙烷与醌酯的 (3 + 3) 环加成反应，以中等至良好的收率构建色满支架。有趣的是，该策略还可以调整为 (3 + 2) 环加成，只需切换路易斯酸来提供苯并呋喃支架。根据所用路易斯酸的选择，同一组前体已用于递送苯并吡喃和苯并呋喃衍生物。
• [3+2] Cyclodimerization of 2-arylcyclopropane-1,1-diesters. Lewis acid induced reversion of cyclopropane umpolung
  作者：Alexey O. Chagarovskiy、Olga A. Ivanova、Ekaterina M. Budynina、Igor V. Trushkov、Mikhail Ya. Melnikov

  DOI：10.1016/j.tetlet.2011.06.059

  日期：2011.8

  A novel Lewis acid catalyzed [3+2] cyclodimerization of 2-arylcyclopropane-1,1-dicarboxylates is reported. It is the first example of a reaction wherein a donor-acceptor cyclopropane provides two carbons in a newly formed ring. The described cyclodimerization represents a general convenient approach to polyfunctionalized cyclopentanes. (C) 2011 Elsevier Ltd. All rights reserved.