ethyl 2-(4-bromobenzoyl)-3-(4-chlorophenyl)-1-cyanocyclopropane-1-carboxylate | 1619915-92-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-(4-bromobenzoyl)-3-(4-chlorophenyl)-1-cyanocyclopropane-1-carboxylate
• CAS: 1619915-92-2
• 化学式: C₂₀H₁₅BrClNO₃
• 分子量: 432.701
• InChiKey: UBLGJCWRTZSNHM-UHFFFAOYSA-N

物化性质

• 沸点：
  561.4±50.0 °C(predicted)
• 密度：
  1.53±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-(4-bromobenzoyl)-3-(4-chlorophenyl)-1-cyanocyclopropane-1-carboxylate 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以84%的产率得到ethyl 6-cyano-2,5-bis(4-bromobenzoyl)-3,4-bis(4-chlorophenyl)benzoate
  参考文献：
  名称：

  Bimolecular Intermolecular-Michael/Intramolecular-Michael/Aromatization Reaction of 1-Cyanocyclopropane 1-Esters or 1,1-Dicyanocyclopropanes: A Straightforward Approach to Fully Substituted Benzenes

  摘要：

  An efficient and straightforward synthetic protocol has been developed for the preparation of fully substituted benzenes via a [3+3]-cyclodimerization reaction of 1-cyanocyclopropane 1-esters or 1,1-dicyanocyclopropanes for the generation of a wide range of structurally interesting significant compounds. The reaction utilizes Et3N-promoted C-C bond cleavage, two new C-C bond formations of 1-cyanocyclopropane 1-ester and simultaneous aromatization by removal of cyano and ester groups in a domino fashion.

  DOI：

  10.1055/s-0034-1379909

文献信息

• Formal [3+2] cycloaddition of 1-cyanocyclopropane 1-ester with pyridine, quinoline or isoquinoline: a general and efficient strategy for construction of cyanoindolizine skeletons
  作者：Juanjuan Liu、Lanxiang Zhou、Weijian Ye、Cunde Wang

  DOI：10.1039/c4cc03267e

  日期：——

  An efficient and straightforward preparation of cyanoindolizine derivatives via a cycloaddition reaction between 1-cyanocyclopropane 1-ester and pyridine or benzopyridine.

  通过1-氰基环丙烷1-酯和吡啶或苯并吡啶之间的环加成反应，高效且直接地制备氰基吲哚啉衍生物。
• DBU-mediated [4 + 1] annulations of donor–acceptor cyclopropanes with carbon disulfide or thiourea for synthesis of 2-aminothiophene-3-carboxylates
  作者：Zhenjie Su、Siran Qian、Shuwen Xue、Cunde Wang

  DOI：10.1039/c7ob01886j

  日期：——

  disulfide or Thiourea for Synthesis of 2-Aminothiophene-3-carboxylates by Zhenjie Su, Siran Qian, Shuwen Xue and Cunde Wang* Dear Editors: We would like to submit the above referenced manuscript for review and possible publication in Organic & Biomolecular Chemistry. The manuscript reports that DBU-mediated [4 + 1] annulations of donor-acceptor cyclopropanes with carbon disulfide or thiourea has been developed

  求职信2017年7月29日Re：DBU介导的[4 +1]供体-受体环丙烷与二硫化碳或硫脲的合成，由苏振杰，钱思然，薛树文和王训*合成2-氨基噻吩-3-羧酸酯尊敬的编辑：我们想将以上引用的手稿提交给《有机与生物分子化学》杂志，以供审阅和发表。该手稿报告说，已开发出DBU介导的供体-受体环丙烷与二硫化碳或硫脲的环化[4 +1]环合反应，用于合成2-氨基噻吩-3-羧酸酯衍生物，该衍生物在结构上具有广泛意义，并且在药理学上具有重要意义。化合物。值得一提的是，这种新近有效的方法使人们可以获得各种结构上不同的2-氨基噻吩-3-羧酸酯衍生物。我们相信该方法的这种实际使用将是合成化学家普遍感兴趣的。谢谢您的考虑。诚挚的，Cunde Wang博士。扬州大学化学化工学院教授，​​扬州225002电话：+ 86-514-8797-5568，传真：+ 86-514-8797-5244电子邮件：wangcd@yzu
• One-Pot Synthesis of Highly Substituted Pyrroles by Three-Component Reactions of Donor-Acceptor Cyclopropanes, Salicylaldehydes, and Ammonium Acetate
  作者：Zhenjie Su、Wenxing Gu、Siran Qian、Shuwen Xue、Cunde Wang

  DOI：10.1002/ejoc.201701674

  日期：2018.2.28

  rile derivatives have been synthesized efficiently by the one‐pot three‐component reactions of donor–acceptor cyclopropanes, salicylaldehydes, and ammonium acetate in the presence of triethylamine. With ammonium acetate as the nitrogen source, a variety of highly substituted pyrroles were obtained in moderate‐to‐excellent yields under mild conditions.

  在三乙胺存在下，通过供体-受体环丙烷，水杨醛和乙酸铵的一锅三组分反应，可以高效合成2-（2,4,5-三取代-吡咯-3-基）乙腈衍生物。以乙酸铵为氮源，在温和条件下以中等至优异的产率获得了各种高度取代的吡咯。
• DBU-Mediated Cyclization of Acylcyclopropanecarboxylates with Amidines: Access to Polysubstituted Pyrimidines
  作者：Shan Wang、Naili Luo、Yan Li、Cunde Wang

  DOI：10.1021/acs.orglett.9b01436

  日期：2019.6.21

  DBU-mediated cyclization of 2-acyl-1-cyanocyclopropanecarboxylates with amidines for the synthesis of multisubstituted pyrimidine derivatives is described. This reaction gives a practical method for producing a diverse set of pyrimidines, having simple experimentation, readily available starting materials, a wide substrate scope, and very good yields.