Methyl 2-[[3-(trifluoromethyl)phenyl]methylideneamino]acetate | 1166397-76-7

• 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: Methyl 2-[[3-(trifluoromethyl)phenyl]methylideneamino]acetate
• 英文别名: methyl 2-[[3-(trifluoromethyl)phenyl]methylideneamino]acetate
• CAS: 1166397-76-7
• 化学式: C₁₁H₁₀F₃NO₂
• 分子量: 245.201
• InChiKey: RCRUQIHKTVAKMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 2-[[3-(trifluoromethyl)phenyl]methylideneamino]acetate 、 马来酸二甲酯 在 C₄₉H₃₉FeNO₂P₂ 、 silver(I) acetate 、 三乙胺 作用下， 以 乙醚 为溶剂， 反应 15.0h， 以94%的产率得到trimethyl (2R,3S,4R,5S)-5-(3-trifluoromethylphenyl)pyrrolidine-2,3,4-tricarboxylate
  参考文献：
  名称：

  Enantioselective Ag(I)-catalyzed [3+2] cycloaddition of azomethine ylides using a chiral ferrocene-based phosphine–phosphoramidite ligand having a stereogenic P-center

  摘要：

  A series of chiral ferrocene-based phosphine-phosphoramidite ligands (PPFAPhos) have been employed in the Ag(I)-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with dimethyl maleate. The results showed that the ligand with a stereogenic P-center in the phosphino moiety displayed the best diastereo- and enantioselectivities, in which LIP to 99% enantiomeric excesses and 99/1 endo/exo selectivities have been achieved. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.02.058
• 作为产物：
  描述：

  3-三氟甲基苯甲醛 、 甘氨酸甲酯盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 Methyl 2-[[3-(trifluoromethyl)phenyl]methylideneamino]acetate
  参考文献：
  名称：

  Copper/GanPhos-Catalyzed 1,3-Dipolar Cycloaddition of Azo­methine Ylides: An Efficient Access to Chiral Pyrrolidine Spirocycles

  摘要：

  标题：摘要 一种高效的铜/GanPhos催化的1,3-偶极环加成反应已报告。这种可行的转化提供了一系列具有一个螺环四元和三个三级立体异构中心的光学活性螺[二氢萘-2,3'-吡咯啉]，产率高，ee值也高。该方案具有高对映选择性和对映选择性，广泛的底物范围和温和的反应条件。

  DOI：

  10.1055/s-0040-1706599

文献信息

• Asymmetric Construction of Pyrrolidines Bearing a Trifluoromethylated Quaternary Stereogenic Center via Cu^I -Catalyzed 1,3-Dipolar Cycloaddition of Azomethine Ylides with β-CF₃ -β,β-Disubstituted Nitroalkenes
  作者：Li-Wei Tang、Bao-Jing Zhao、Li Dai、Man Zhang、Zhi-Ming Zhou

  DOI：10.1002/asia.201600941

  日期：2016.9.6

  convenient method has been developed for the synthesis of optically active pyrrolidines bearing a quaternary stereogenic center containing a CF3 group at the C‐3 position of the pyrrolidine ring. The synthesis system, CuI/Si‐FOXAP‐catalyzed exo‐selective 1,3‐dipolar cycloaddition of azomethine ylides with β‐CF3‐β,β‐disubstituted nitroalkenes, provides pyrrolidines with high diastereoselectivities (up to

  已经开发了一种直接便捷的方法来合成光学活性的吡咯烷，该吡咯烷在吡咯烷环的C-3位置带有一个含CF 3基团的季立体中心。合成体系，铜我/硅FOXAP催化外型与β-CF甲亚胺叶立德-选择性1,3-偶极环加成3 -β，β二取代硝基烯烃，提供吡咯烷以高非对映选择性（高达> 98:2博士）和出色的对映选择性（高达> 99.9 ee），并且在温和条件下对各种底物都具有良好的性能。
• Modular Access to Tetrasubstituted N‐H Pyrroles by Catalytic 1,3‐Dipolar Cycloaddition of Azomethine Ylides and α,β‐Ynones
  作者：Qian Huang、Zi-Han Li、Zhen-Ni Zhao、Bo-Ting Chen、Feng-Kai He、Yi-Yong Huang

  DOI：10.1002/ejoc.202400437

  日期：——

  Tetrasubstituted N−H pyrroles were accessed through the tandem copper(II)-catalyzed 1,3-dipolar cycloaddition of α,β-ynones and glycine iminoesters, followed by a copper(II)-promoted oxidative dehydrogenative aromatization reaction in air. Fully substituted pyrroles could then be obtained by N-alkylation.

  通过串联铜(II)催化的α,β-炔酮和甘氨酸亚氨基酯的1,3-偶极环加成，然后在空气中进行铜(II)促进的氧化脱氢芳构化反应，获得四取代的NH吡咯。然后可以通过N-烷基化获得完全取代的吡咯。
• Copper/GanPhos-Catalyzed 1,3-Dipolar Cycloaddition of Azo­methine Ylides: An Efficient Access to Chiral Pyrrolidine Spirocycles
  作者：Zhenjie Gan、Er-Qing Li、Ke Li、Hui Zhang

  DOI：10.1055/s-0040-1706599

  日期：2021.4

  A highly efficient copper/GanPhos-catalyzed 1,3-dipolar cyclo­addition­ of azomethine ylides is reported. This viable transformation provides a series of optically active spiro[dihydronaphthalene-2,3′-pyrrolidine]s, bearing one spiro quaternary and three tertiary stereogenic centers, in good yields and with high ee values. This protocol features high diastereo- and enantioselectivity, broad substrate scope and mild reaction conditions.

  标题：摘要 一种高效的铜/GanPhos催化的1,3-偶极环加成反应已报告。这种可行的转化提供了一系列具有一个螺环四元和三个三级立体异构中心的光学活性螺[二氢萘-2,3'-吡咯啉]，产率高，ee值也高。该方案具有高对映选择性和对映选择性，广泛的底物范围和温和的反应条件。
• Enantioselective Ag(I)-catalyzed [3+2] cycloaddition of azomethine ylides using a chiral ferrocene-based phosphine–phosphoramidite ligand having a stereogenic P-center
  作者：Sai-Bo Yu、Xiang-Ping Hu、Jun Deng、Dao-Yong Wang、Zheng-Chao Duan、Zhuo Zheng

  DOI：10.1016/j.tetasy.2009.02.058

  日期：2009.3

  A series of chiral ferrocene-based phosphine-phosphoramidite ligands (PPFAPhos) have been employed in the Ag(I)-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with dimethyl maleate. The results showed that the ligand with a stereogenic P-center in the phosphino moiety displayed the best diastereo- and enantioselectivities, in which LIP to 99% enantiomeric excesses and 99/1 endo/exo selectivities have been achieved. (C) 2009 Elsevier Ltd. All rights reserved.