diethyl trans-2-benzoyl-3-(4-nitrophenyl)-cyclopropane-1,1-dicarboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diethyl trans-2-benzoyl-3-(4-nitrophenyl)-cyclopropane-1,1-dicarboxylate
• 英文别名: diethyl (2R,3S)-2-benzoyl-3-(4-nitrophenyl)cyclopropane-1,1-dicarboxylate
• 化学式: C₂₂H₂₁NO₇
• 分子量: 411.411
• InChiKey: DEGSPNHOEGUZAW-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  diethyl trans-2-benzoyl-3-(4-nitrophenyl)-cyclopropane-1,1-dicarboxylate 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以60%的产率得到diethyl trans-2-[1-(4-nitrophenyl)-3-oxo-indan-2-yl]malonate
  参考文献：
  名称：

  Lewis Acid-Mediated Transformations oftrans-2-Aroyl-3-aryl- cyclopropane-1,1-dicarboxylates into 2-Pyrones and 1-Indanones

  摘要：

  Abstracttrans‐2‐Aroyl‐3‐arylcyclopropane‐1,1‐dicarboxylates upon treatment with aluminium(III) chloride (AlCl3) underwent ring‐opening, fragmentation, recombination and lactonization to give highly substituted 2‐pyrones. Alternatively, when treated with titanium(IV) chloride (TiCl4), the cyclopropane diesters underwent a Nazarov cyclization to afford 1‐indanones with high diastereoselectivity.magnified image

  DOI：

  10.1002/adsc.201300861
• 作为产物：
  描述：

  2-(1-(4-硝基苯基)-3-氧代-3-苯基丙基)丙二酸二乙酯 在 亚碘酰苯 、 四丁基碘化铵 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以92%的产率得到diethyl trans-2-benzoyl-3-(4-nitrophenyl)-cyclopropane-1,1-dicarboxylate
  参考文献：
  名称：

  溶剂控制的氧化环化反应，可高度合成官能化的氧杂环丁烷和环丙烷

  摘要：

  报道了碘代苯和碘化四丁基铵的组合物对丙二酸酯与查耳酮的迈克尔加合物的有效溶剂控制的氧化环化反应。高官能度的氧杂环丁烷和环丙烷以中等到极好的收率和高非对映选择性发散地合成。

  DOI：

  10.1021/ol9012102

文献信息

• FeCl₃-Promoted [3 + 2] Annulations of γ-Butyrolactone Fused Cyclopropanes with Heterocumulenes
  作者：Manli Feng、Pengfei Yang、Gaosheng Yang、Wenlong Chen、Zhuo Chai

  DOI：10.1021/acs.joc.7b02561

  日期：2018.1.5

  The [3 + 2] annulations of γ-butyrolactone fused donor–acceptor (D–A) cyclopropanes with aromatic isothiocyanates and dialkyl carbodiimides promoted by FeCl3 is reported. A series of bicyclic/polycyclic γ-butyrolactone fused thioimidates and γ-butyrolactone fused amidines containing four contiguous stereogenic centers were obtained in excellent yields as single stereoisomers.

  据报道，γ-丁内酯稠合的供体-受体（DA）环丙烷与芳族异硫氰酸酯和FeCl 3促进的二烷基碳二亚胺的环化[3 + 2] 。以优异的产率获得了一系列具有四个收成的立体异构中心的双环/多环γ-丁内酯稠合的硫代亚氨酸酯和γ-丁内酯稠合的am。
• AlCl3-promoted [3 + 2] annulation of cis-2,3-disubstituted cyclopropane 1,1-diesters with isothiocyanates: stereoselective synthesis of densely substituted 2-iminodihydrothiophenes
  作者：Yongxian Sun、Gaosheng Yang、Zhuo Chai、Xiaolong Mu、Jun Chai

  DOI：10.1039/c3ob41678j

  日期：——

  cis-2,3-Disubstituted cyclopropane 1,1-diesters were found to be much more reactive than their corresponding trans-isomers in the AlCl3-promoted [3 + 2]-annulations with isothiocyanates. The reaction with the cis-cyclopropanes proceeded to completion within minutes, providing a variety of densely substituted diastereomerically pure 2-iminodihydrothiophenes in moderate to excellent yields.

  人们发现顺式-2,3-二取代环丙烷1,1-二酯在AlCl3促进的与异硫氰酸酯的[3 + 2]-成环反应中比其相应的反式异构体更具反应性。与顺式环丙烷的反应在几分钟内完成，以中等至优异的产率提供各种密集取代的非对映体纯2-亚氨基二氢噻吩。
• Highly Diastereoselective Synthesis of 1-Pyrrolines <i>via</i> SnCl₄-Promoted [3 + 2] Cycloaddition between Activated Donor–Acceptor Cyclopropanes and Nitriles
  作者：Gopal Sathishkannan、Kannupal Srinivasan

  DOI：10.1021/ol2024423

  日期：2011.11.18

  Activated donor–acceptor cyclopropanes underwent formal [3 + 2] cycloaddition with nitriles in the presence of SnCl4. The product 1-pyrrolines were isolated as single cis-diastereomers in moderate to good yields.

  活化的供体-受体环丙烷在SnCl 4的存在下与腈进行正式的[3 + 2]环加成反应。产物1-吡咯啉以中等至良好的产率分离为单一的顺式-非对映异构体。
• Scandium(III) Triflate-Catalyzed Reaction of Aroyl-Substituted Donor–Acceptor Cyclopropanes with 1-Naphthylamines: Access to Dibenzo[<i>c</i>,<i>h</i>]acridines
  作者：Murugesan Thangamani、Kannupal Srinivasan

  DOI：10.1021/acs.joc.0c02105

  日期：2021.1.1

  The reaction of aroyl-substituted donor–acceptor (D–A) cyclopropanes with two equivalents of 1-naphthylamines in the presence of a catalytic amount of scandium(III) triflate provides access to dibenzo[c,h]acridines. The key steps of the transformation are the formation of nucleophilic ring-opening products from the D–A cyclopropanes and 1-naphthylamines and their subsequent fragmentation and cyclization

  在催化量的三氟甲磺酸（（III）存在下，芳酰基取代的供体-受体（DA）环丙烷与两当量的1-萘胺的反应提供了二苯并[ c，h ] h啶的进入途径。转化的关键步骤是由D–A环丙烷和1-萘胺形成亲核开环产物，然后将其裂解和环化。该方法具有合理的底物范围，并且以50-70％的产率形成产品。
• SnCl₄-Promoted [3+2] Annulation of γ-Butyrolactone-Fused Donor–Acceptor Cyclopropanes with Nitriles: Access to γ-Butyrolactone-Fused 1-Pyrrolines
  作者：V. John Tamilarasan、Kannupal Srinivasan

  DOI：10.1021/acs.joc.9b01155

  日期：2019.7.5

  γ-butyrolactone-fused donor–acceptor cyclopropanes with nitriles has been explored for the access of γ-butyrolactone-fused 1-pyrrolines. The annulation was promoted by tin(IV) chloride, and the products were obtained as single diastereomers in moderate to good yields. The products were synthetically important, and a couple of them were subjected to tandem reductive ring opening/cyclization to give the respective

  已经探索了将γ-丁内酯融合的供体-受体环丙烷与腈进行[3 + 2]环合，以获取γ-丁内酯融合的1-吡咯啉。用氯化锡（IV）促进环化，并以中等至良好的收率获得单一非对映异构体形式的产物。产物在合成上很重要，并且将其中的一些进行串联还原性开环/环化，从而以良好的产率得到各自的γ-丁内酯稠合的γ-丁内酰胺。