(1R,3aR,6aS)-methyl 1-isopropyl-4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrrole-1-carboxylate | 1372866-15-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (1R,3aR,6aS)-methyl 1-isopropyl-4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrrole-1-carboxylate
• 英文别名: methyl (3R,3aS,6aR)-4,6-dioxo-5-phenyl-3-propan-2-yl-3a,6a-dihydropyrrolo[3,4-c]pyrrole-3-carboxylate
• CAS: 1372866-15-3
• 化学式: C₁₇H₁₈N₂O₄
• 分子量: 314.341
• InChiKey: VCNCOTMXCGBENP-OGHNNQOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,3aR,6aS)-methyl 1-isopropyl-4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrrole-1-carboxylate 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以60%的产率得到(1R,3aR,6aS)-methyl 1-isopropyl-4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate
  参考文献：
  名称：

  Au-Catalyzed Asymmetric Formal [3 + 2] Cycloaddition of Isocyanoacetates with Maleimides

  摘要：

  An efficient protocol for the Au-I-catalyzed asymmetric formal [3 + 2] cycloaddition of isocyanoacetates with phenylmaleimide has been developed. In the presence of cationic Au-I/DTBM-segphos complex, excellent diastereoselectivity and high levels of enantioselectivity (up to 97% cc) have been attained with a variety of alpha-substituted isocyanoacetates. The synthetic potential of the resulting enantioenriched 1-pyrrolines has been demonstrated by the preparation of highly substituted pyrrolidines bearing a quaternary stereocenter.

  DOI：

  10.1021/jo3003425
• 作为产物：
  描述：

  在 air 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 22.5h， 生成 (1R,3aR,6aS)-methyl 1-isopropyl-4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrrole-1-carboxylate
  参考文献：
  名称：

  功能化偶氮甲碱叶立德的生成及其在立体选择性杂环合成中的应用：C-未取代的腈叶立德环加成反应的等效过程

  摘要：

  摘要 通过NH-偶氮甲碱叶立德的环加成和随后的环加合物在酸性条件下的裂变反应，实现了相当于C-未取代(CH)腈叶立德环加成反应的合成过程。在 4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde 系统中由热 1,2-prototropy 生成的 NH-azomethine 叶立德与马来酰亚胺在极其温和的条件下进行环加成反应提供脯氨酸衍生物。在 85 °C 下在 AcOH 中加热它们的加合物会导致脯氨酸和杂环部分之间的 C-C 键断裂，得到母体杂环系统和脱氢脯氨酸衍生物，它被认为是 C-未取代 (CH) 腈叶立德的环加合物。这种环加成裂变反应序列可应用于一锅三组分反应。

  DOI：

  10.1016/j.tet.2006.12.004

文献信息

• Asymmetric Formal [3+2] Cycloaddition Reaction of α-Aryl Isocyanoesters with<i>N</i>-Aryl Maleimides by Bifunctional Cinchona Alkaloids-Based Squaramide/AgSbF₆Cooperative Catalysis
  作者：Mei-Xin Zhao、Deng-Ke Wei、Fei-Hu Ji、Xiao-Li Zhao、Min Shi

  DOI：10.1002/asia.201200686

  日期：2012.12

  better to be cooperative: A highly diastereo‐ and enantioselective asymmetric [3+2] cycloaddition reaction of α‐aryl isocyanoacetates with N‐aryl maleimides through cooperative catalysis of cinchona alkaloid‐derived squaramide/AgSbF6 was developed. A wide range of optically active, substituted 1,3a,4,5,6,6a‐hexahydropyrrolo[3,4‐c] pyrrole derivatives was obtained in high yields (up to 98 %), high diastereoselectivities

  最好是协同作用：通过金鸡纳生物碱衍生的方酸酰胺/ AgSbF 6的协同催化，开发了α-芳基异氰基乙酸酯与N-芳基马来酰亚胺的高度非对映体和对映选择性不对称[3 + 2]环加成反应。以高收率（高达98％），高非对映选择性（> 20：1 dr ），并且在温和的反应条件下对映体的选择性良好（高达ee的92％）。
• Au-Catalyzed Asymmetric Formal [3 + 2] Cycloaddition of Isocyanoacetates with Maleimides
  作者：Silvia Padilla、Javier Adrio、Juan C. Carretero

  DOI：10.1021/jo3003425

  日期：2012.4.20

  An efficient protocol for the Au-I-catalyzed asymmetric formal [3 + 2] cycloaddition of isocyanoacetates with phenylmaleimide has been developed. In the presence of cationic Au-I/DTBM-segphos complex, excellent diastereoselectivity and high levels of enantioselectivity (up to 97% cc) have been attained with a variety of alpha-substituted isocyanoacetates. The synthetic potential of the resulting enantioenriched 1-pyrrolines has been demonstrated by the preparation of highly substituted pyrrolidines bearing a quaternary stereocenter.
• Generation of functionalized azomethine ylides and their application to stereoselective heterocycle synthesis: an equivalent process of C-unsubstituted nitrile ylide cycloaddition reaction
  作者：Keisuke Kawashima、Akikazu Kakehi、Michihiko Noguchi

  DOI：10.1016/j.tet.2006.12.004

  日期：2007.2

  Abstract The synthetic process equivalent to C-unsubstituted (CH) nitrile ylides cycloaddition reaction is achieved via cycloaddition of NH-azomethine ylide and the following fission reaction of the cycloadducts under acidic conditions. Cycloaddition of NH-azomethine ylide generated by a thermal 1,2-prototropy in 4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde system with maleimides provides proline

  摘要 通过NH-偶氮甲碱叶立德的环加成和随后的环加合物在酸性条件下的裂变反应，实现了相当于C-未取代(CH)腈叶立德环加成反应的合成过程。在 4-oxo-4H-pyrido[1,2-a]pyrimidine-3-carbaldehyde 系统中由热 1,2-prototropy 生成的 NH-azomethine 叶立德与马来酰亚胺在极其温和的条件下进行环加成反应提供脯氨酸衍生物。在 85 °C 下在 AcOH 中加热它们的加合物会导致脯氨酸和杂环部分之间的 C-C 键断裂，得到母体杂环系统和脱氢脯氨酸衍生物，它被认为是 C-未取代 (CH) 腈叶立德的环加合物。这种环加成裂变反应序列可应用于一锅三组分反应。