dimethyl trans-2-benzoyl-3-phenylcyclopropane-1,1-dicarboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl trans-2-benzoyl-3-phenylcyclopropane-1,1-dicarboxylate
• 英文别名: dimethyl (2R,3S)-2-benzoyl-3-phenylcyclopropane-1,1-dicarboxylate
• 化学式: C₂₀H₁₈O₅
• 分子量: 338.36
• InChiKey: FGAIUQYDWXTGLL-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl trans-2-benzoyl-3-phenylcyclopropane-1,1-dicarboxylate 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以80%的产率得到methyl 2-oxo-5,6-diphenyl-2H-pyran-3-carboxylate
  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-(3-氧代-1,3-二苯基丙基)-丙二酸二甲酯 在 叔丁基过氧化氢 、 N-碘代丁二酰亚胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.5h， 以31.4%的产率得到dimethyl trans-2-benzoyl-3-phenylcyclopropane-1,1-dicarboxylate
  参考文献：
  名称：

  次碘酸盐催化的1,3-二羰基化合物的麦尔酮与迈克尔加成物的氧化环化：一种简便，通用的取代呋喃和环丙烷的方法。

  摘要：

  通过次碘酸盐催化，开发了查耳酮的迈克尔加合物与1,3-二羰基化合物的氧化环化反应，可用于呋喃或环丙烷的发散合成。主要产品的选择性合成...

  DOI：

  10.1039/c6cc06624k

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。
• Stereocontrolled Synthesis of <i>trans</i>/<i>cis</i>-2,3-Disubstituted Cyclopropane-1,1-diesters and Applications in the Syntheses of Furanolignans
  作者：Yue Shen、Jun Chai、Gaosheng Yang、Wenlong Chen、Zhuo Chai

  DOI：10.1021/acs.joc.8b01798

  日期：2018.10.19

  A new Michael addition/intramolecular alkylation sequence of (Z)-3-(2-bromo-3-arylacryloyl)oxazolidin-2-ones and malonates was developed. By a simple switch of the reaction conditions including the base promoter, solvent, and reaction temperature, both of the cis- and trans-isomers of a series of oxazolidinone-containing 2,3-disubstituted cyclopropane-1,1-diesters could be obtained in good-to-excellent

  建立了新的（Z）-3-（2-溴-3-芳基丙烯酰基）恶唑烷-2-酮和丙二酸酯的迈克尔加成/分子内烷基化序列。通过简单地改变反应条件，包括碱助催化剂，溶剂和反应温度，就可以得到一系列含恶唑烷酮的2,3-二取代的环丙烷-1,1-二酯的顺式和反式异构体。产量极佳，非对映选择性极好。在（±）-尿嘧啶和（±）-维他汀的立体异构体的非对映选择性合成中证明了环丙烷产物的效用，涉及以醛或胡椒醛为关键步骤的AlCl 3促进的[3 + 2]环化。
• Solvent-Controlled Oxidative Cyclization for Divergent Synthesis of Highly Functionalized Oxetanes and Cyclopropanes
  作者：Yang Ye、Chen Zheng、Renhua Fan

  DOI：10.1021/ol9012102

  日期：2009.7.16

  An efficient solvent-controlled oxidative cyclization of Michael adducts of malonates with chalcones with the combination of iodosobenzene and tetrabutylammonium iodide is reported. Highly functionalized oxetanes and cyclopropanes were divergently synthesized in moderate to excellent yields with high diastereoselectivity.

  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。
• PCl5-mediated ring-openings of trans-2,3-disubstituted cyclopropane-1,1-diesters: A stereoselective way to trisubstituted vinyl chlorides
  作者：Deju Hua、Pengfei Yang、Yue Shen、Gaosheng Yang、Zhuo Chai

  DOI：10.1016/j.tet.2017.01.022

  日期：2017.2

  trans-2-aroyl-3-aryl-cyclopropane-1,1-dicarboxylates involving the cleavage of the C2C3 bond of the cyclopropane ring mediated by PCl5 was disclosed. This reaction provides an efficient metal-free way to functionalized stereodefined trisubstituted Z-vinyl chlorides in moderate to good yields. A tentative mechanism for the reaction has been proposed.

  公开了一种空前的反式-2-芳酰基-3-芳基-环丙烷-1，1-二羧酸酯的开环模式，其涉及由PCl 5介导的环丙烷环的C 2 C 3键的裂解。该反应提供了一种有效的无金属的方法，以中等至良好的收率来官能化立体确定的三取代的Z-氯乙烯。已经提出了该反应的暂定机理。
• Diastereoselective Hydroacylation of Cyclopropenes by Visible-Light Photocatalysis
  作者：Sourabh Biswas、Palasetty Chandu、Sumit Garai、Devarajulu Sureshkumar

  DOI：10.1021/acs.orglett.3c03095

  日期：2023.11.3

  hydroacylation of cyclopropene is disclosed for synthesizing various 2-acylcyclopropane derivatives under mild reaction conditions. High functional group tolerance of this protocol features a novel route to access a divergent synthesis of acylated cyclopropane in a diastereoselective manner by photoinduced decarboxylation of α-ketoacid followed by acyl radical addition to cyclopropene. Additionally, the

  公开了一种有效且通用的环丙烯加氢酰化策略，用于在温和的反应条件下合成各种2-酰基环丙烷衍生物。该方案的高官能团耐受性特点是通过光诱导α-酮酸脱羧，然后将酰基自由基加成到环丙烯上，以非对映选择性方式实现酰化环丙烷的发散合成。此外，以反式选择性方式在最少取代的烯属碳中心区域选择性添加酰基使得该方案对天然产物开发更具吸引力。