dimethyl 2-benzylidenecyclopropane-1,1-dicarboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dimethyl 2-benzylidenecyclopropane-1,1-dicarboxylate
• 英文别名: Dimethyl 2-benzylidenecyclopropane-1,1-dicarboxylate
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: BCMLXNVHPNVCPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  dimethyl 2-benzylidenecyclopropane-1,1-dicarboxylate 在 ytterbium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 以93%的产率得到dimethyl 2-(1H-inden-2-yl)malonate
  参考文献：
  名称：

  Lewis Acid Catalyzed Ring-Opening Intramolecular Friedel−Crafts Alkylation of Methylenecyclopropane 1,1-Diesters

  摘要：

  The first Friedel-Crafts reaction initiated by the direct generation of a carbocation at the C3 position of MCP 1,1-diesters through distal-bond cleavage was presented. The described method supplied a new synthetic strategy to prepare indene and hydronaphthalene derivatives in moderate to excellent yields under mild conditions.

  DOI：

  10.1021/ol802301e
• 作为产物：
  描述：

  2-叠氮丙二酸二甲酯 、 丙-1,2-二烯基苯 在 dirhodium tetraacetate 作用下， 生成 dimethyl 2-benzylidenecyclopropane-1,1-dicarboxylate
  参考文献：
  名称：

  An efficient and stereoselective cycloaddition of C-aryl and C-amido nitrones to dimethyl 2-benzylidenecyclopropane-1,1-dicarboxylate

  摘要：

  1,3-Dipolar cycloalditions of dimethyl 2-benzylidenecyclopropane-1,1-dicarboxylate and a number of C-aryl or C-amido nitrones proceed with high efficiency and selectivity with the formation of only one isomeric spiral[cyclopropane-1,4-isoxazolidine] cycloadduct. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.013

文献信息

• A Highly Site-, Regio-, and Stereoselective Lewis Acid Catalyzed Formal [3+3] Cycloaddition of Methylenecyclopropane-1,1-Diesters with C,N-Diarylnitrones
  作者：Bao Hu、Jianlin Zhu、Siyang Xing、Jie Fang、Ding Du、Zhongwen Wang

  DOI：10.1002/chem.200801990

  日期：2009.1.2

  Another pathway: A new type of Lewis acid promoted [3+3] cycloaddition of methylenecyclopropane‐1,1‐diesters with C,N‐diarylnitrones is disclosed. This cycloaddition is highly site‐, regio‐, and stereoselective and proceeds in moderate‐to‐excellent yields. A three‐component one‐pot version of the cycloaddition is also reported.

  另一途径：公开了一种新型的路易斯酸促进了亚甲基环丙烷-1,1-二酯与C，N-二芳基硝酮的[3 + 3]环加成反应。这种环加成反应具有很高的位点，区域和立体选择性，产率中等至优异。还报告了三组分一锅法的环加成反应。
• Cycloaddition of C,C-Disubstituted Ketonitrones with Acceptor Methylenecyclopropanes and Subsequent Rearrangement Cascade of 5-Spirocyclopropane-isoxazolidines
  作者：Tung Q. Tran、Vyacheslav V. Diev、Galina L. Starova、Vladislav V. Gurzhiy、Alexander P. Molchanov

  DOI：10.1002/ejoc.201200039

  日期：2012.4

  A new reaction cascade to give tricyclic cores of 2,4-dihydro-1H-azeto[1,2-a]quinolines (benzocarbacephems) and pyrrolo[1,2-a]quinolines starting from acyclic N-aryl ketonitrones and acceptor ring substituted methylenecyclopropanes has been reported. This reaction includes 1,3-dipolar cycloaddition of N-aryl-C,C-diaryl or N-aryl-C,C-bis(methoxycarbonyl) nitrones 1 to the double bond of dimethyl me

  从无环 N-芳基酮硝酮和受体环取代的 2,4-二氢-1H-azeto[1,2-a] 喹啉（苯并碳头烯类）和吡咯并 [1,2-a] 喹啉的三环核心的新反应级联亚甲基环丙烷已有报道。该反应包括 N-芳基-C,C-二芳基或 N-芳基-C,C-双（甲氧基羰基）硝酮 1 与亚甲基环丙烷-1,2-二甲酸二甲酯 2 或亚苄基环丙烷的双键的 1,3-偶极环加成反应-1,1-二羧酸酯 3，然后对最初形成的 5-螺环丙烷-异恶唑烷环加合物进行 Brandi-Guarna 重排，得到 2,4-二氢-1H-azeto[1,2-a] 喹啉 4 或吡咯并 [1,2] -a]喹啉 6.
• An efficient and stereoselective cycloaddition of C-aryl and C-amido nitrones to dimethyl 2-benzylidenecyclopropane-1,1-dicarboxylate
  作者：Tung Q. Tran、Vyacheslav V. Diev、Alexander P. Molchanov

  DOI：10.1016/j.tet.2011.02.013

  日期：2011.4

  1,3-Dipolar cycloalditions of dimethyl 2-benzylidenecyclopropane-1,1-dicarboxylate and a number of C-aryl or C-amido nitrones proceed with high efficiency and selectivity with the formation of only one isomeric spiral[cyclopropane-1,4-isoxazolidine] cycloadduct. (C) 2011 Elsevier Ltd. All rights reserved.
• Lewis Acid Catalyzed Ring-Opening Intramolecular Friedel−Crafts Alkylation of Methylenecyclopropane 1,1-Diesters
  作者：Bao Hu、Siyang Xing、Zhongwen Wang

  DOI：10.1021/ol802301e

  日期：2008.12.4

  The first Friedel-Crafts reaction initiated by the direct generation of a carbocation at the C3 position of MCP 1,1-diesters through distal-bond cleavage was presented. The described method supplied a new synthetic strategy to prepare indene and hydronaphthalene derivatives in moderate to excellent yields under mild conditions.