methyl 2-(5-bromo-3-((tert-butoxycarbonyl)oxy)-1-methyl-2-oxoindolin-3-yl)acrylate | 1321139-61-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl 2-(5-bromo-3-((tert-butoxycarbonyl)oxy)-1-methyl-2-oxoindolin-3-yl)acrylate
• 英文别名: Methyl 2-[5-bromo-1-methyl-3-[(2-methylpropan-2-yl)oxycarbonyloxy]-2-oxoindol-3-yl]prop-2-enoate
• CAS: 1321139-61-0
• 化学式: C₁₈H₂₀BrNO₆
• 分子量: 426.264
• InChiKey: QKPNJZZGZXETGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  β-硝基苯乙烯 、 methyl 2-(5-bromo-3-((tert-butoxycarbonyl)oxy)-1-methyl-2-oxoindolin-3-yl)acrylate 在 α-isocupreine 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以73%的产率得到methyl (R)-5′-bromo-1′-methyl-2′-oxo-5-phenylspiro[cyclopenta[2,4]diene-1,3′-indoline]-2-carboxylate
  参考文献：
  名称：

  Tertiary-Amine-Catalyzed Asymmetric [3+2] Annulations of Morita–Baylis–Hillman Carbonates of Isatins with Nitroolefins to Construct Spirooxindoles

  摘要：

  An enantioselective [3+2] annulation of nitroolefins with racemic Morita-Baylis-Hillman carbonates of isatins catalyzed by -isocupreine has been developed. Chiral spirocyclic 2-oxindoles bearing an unusual cyclopentadiene motif were produced in excellent enantioselectivity (up to 98% ee) after the tandem elimination of HNO2 in the presence of DIPEA.

  DOI：

  10.1055/s-0034-1378716

文献信息

• Pseudo‐Stereodivergent Synthesis of Enantioenriched Tetrasubstituted Alkenes by Cascade 1,3‐Oxo‐Allylation/Cope Rearrangement
  作者：Peng Chen、Yue Li、Zhi‐Chao Chen、Wei Du、Ying‐Chun Chen

  DOI：10.1002/anie.202000044

  日期：2020.4.27

  of highly enantioenriched tetrasubstituted alkene architectures from isatin-based Morita-Baylis-Hillman carbonates and allylic derivatives, under the cooperative catalysis of a tertiary amine and a chiral iridium complex. The success of the switchable construction of the tetrasubstituted alkene motif relies on the diastereodivergent 1,3-oxo-allylation reaction between N-allylic ylides and chiral π-allyliridium

  具有两个或多个立体生成中心的立体异构体的催化非对映异构构型已得到广泛研究。相比之下，尚未认识到将另一种立体成因元素，即涉及多取代的烯烃基团的Z / E构型，可转换地引入光学活性立体异构体中。在此公开的是在叔胺和手性铱配合物的协同催化下，由基于Isatin的Morita-Baylis-Hillman碳酸盐和烯丙基衍生物合成的高度对映体富集的四取代烯烃构筑物的拟立体立体异构体。四取代烯烃基序可转换结构的成功取决于非对映异构体1，
• Enantioselective [3+2] annulation of isatin-derived MBH-carbonates and 3-nitroindoles enabled by a bifunctional DMAP-thiourea
  作者：Ming-Shun Mei、Yu-Hui Wang、Qing Hu、Qing-Hua Li、Da-Yu Shi、Dingding Gao、Guangbo Ge、Guo-Qiang Lin、Ping Tian

  DOI：10.1039/d0cc04462h

  日期：——

  Highly enantioselective [3+2] annulation of isatin-derived MBH-carbonates and 3-nitroindoles was achieved by a chiral DMAP-thiourea bifunctional catalyst.

  通过手性DMAP-硫脲双功能催化剂，实现了异喹啉衍生的MBH-碳酸酯和3-硝基吲哚的高对映选择性[3+2]环化。
• Substrate-controlled switchable asymmetric annulations to access polyheterocyclic skeletons
  作者：Kai-Kai Wang、Pan Wang、Qin Ouyang、Wei Du、Ying-Chun Chen

  DOI：10.1039/c6cc06148f

  日期：——

  domino process from Morita-Baylis-Hillman carbonates of isatins and acrylate and [small alpha]-cyano-[small alpha],[small beta]-unsaturated ketones to deliver highly enantioenriched tetrahydrofuro[2',3':4,5]pyrano[2,3-b]indoles was disclosed catalysed by cinchona-derived tertiary amines, involving [small alpha]-regioselective cyclopropanation, ring-opening,...

  靛红和丙烯酸的Morita-Baylis-Hillman碳酸盐和[小α]-氰基-[小α]，[小β]-不饱和酮的出乎意料的多米诺法，可以提供高度对映体富集的四氢呋喃[2'，3'：4,5公开了由金鸡纳衍生的叔胺催化的]吡喃并[2,3-b]吲哚，涉及[小α]-区域选择性环丙烷化，开环，...。
• Asymmetric [4 + 3] Annulations for Constructing Divergent Oxepane Frameworks via Cooperative Tertiary Amine/Transition Metal Catalysis
  作者：Zhi Chen、Zhi-Chao Chen、Wei Du、Ying-Chun Chen

  DOI：10.1021/acs.orglett.1c03279

  日期：2021.11.5

  We report asymmetric [4 + 3] annulations between isatin-derived Morita–Baylis–Hillman carbonates and two types of vinyl carbonates synergistically catalyzed by tertiary amines and transition metals, through chemoselective assemblies of in situ formed allylic ylides and metal-containing 1,4-dipoles. A range of oxepane frameworks are generally constructed in moderate to good yields with high stereocontrol

  我们报告了靛红衍生的 Morita-Baylis-Hillman 碳酸盐和两种由叔胺和过渡金属协同催化的碳酸乙烯酯之间的不对称 [4 + 3] 环化，通过原位形成的烯丙基叶立德和含金属 1,4 的化学选择性组装-偶极子。一系列氧杂环丁烷骨架通常以中等至良好的产率构建，具有高立体控制。此外，通过调整叔胺和金属催化剂，可以得到带有邻位立体中心的产品的所有四种非对映异构体。
• Organocatalytic asymmetric allylic amination of Morita–Baylis–Hillman carbonates of isatins
  作者：Hang Zhang、Shan-Jun Zhang、Qing-Qing Zhou、Lin Dong、Ying-Chun Chen

  DOI：10.3762/bjoc.8.139

  日期：——

  The investigation of a Lewis base catalyzed asymmetric allylic amination of Morita-Baylis-Hillman carbonates derived from isatins afforded an electrophilic pathway to access multifunctional oxindoles bearing a C3-quaternary stereocenter, provided with good to excellent enantioselectivity (up to 94% ee) and in high yields (up to 97%).

  路易斯碱催化源自靛红的 Morita-Baylis-Hillman 碳酸盐的不对称烯丙基胺化提供了一条亲电途径来获得带有 C3-四元立体中心的多功能氧化吲哚，提供良好到出色的对映选择性（高达 94% ee）和高产量（高达 97%）。