methyl 2-(3-methyl-1H-indole-1-carbonyl)acrylate | 1338700-83-6

• 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-(3-methyl-1H-indole-1-carbonyl)acrylate
• CAS: 1338700-83-6
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: LULFJTJSZCJXIM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  48.3
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(3-methyl-1H-indole-1-carbonyl)acrylate 在 indium(III) triflate 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以47%的产率得到methyl 9-methyl-3-oxo-2,3-dihydro-1H-pyrrolo[1,2-a]indole-2-carboxylate
  参考文献：
  名称：

  Diastereoselective Intramolecular Friedel–Crafts Cyclizations of Substituted Methyl 2-(1H-indole-1-carbonyl)acrylates: Efficient Access to Functionalized 1H-Pyrrolo[1,2-a]indoles

  摘要：

  A general, catalytic method for the diastereoselective synthesis of functionalized 1H-pyrrolo[1,2-a]indoles via an intramolecular Friedel-Crafts alkylation of N-acyl indoles Is reported. Products were obtained In excellent yields (up to 98%) with high diastereoselectivities (up to >25:1 dr).

  DOI：

  10.1021/ol202431x
• 作为产物：
  描述：

  3-甲基吲哚 在 copper diacetate 、 溶剂黄146 作用下， 反应 3.0h， 生成 methyl 2-(3-methyl-1H-indole-1-carbonyl)acrylate
  参考文献：
  名称：

  Diastereoselective Intramolecular Friedel–Crafts Cyclizations of Substituted Methyl 2-(1H-indole-1-carbonyl)acrylates: Efficient Access to Functionalized 1H-Pyrrolo[1,2-a]indoles

  摘要：

  A general, catalytic method for the diastereoselective synthesis of functionalized 1H-pyrrolo[1,2-a]indoles via an intramolecular Friedel-Crafts alkylation of N-acyl indoles Is reported. Products were obtained In excellent yields (up to 98%) with high diastereoselectivities (up to >25:1 dr).

  DOI：

  10.1021/ol202431x

文献信息

• A Catalytic Diastereoselective Formal [5+2] Cycloaddition Approach to Azepino[1,2-<i>a</i>]indoles: Putative Donor-Acceptor Cyclobutanes as Reactive Intermediates
  作者：Raynold Shenje、M. Cynthia Martin、Stefan France

  DOI：10.1002/anie.201408429

  日期：2014.12.8

  A catalytic formal [5+2] cycloaddition approach to the diastereoselective synthesis of azepino[1,2‐a]indoles is reported. The reaction presumably proceeds through a Lewis acid catalyzed formal [2+2] cycloaddition of an alkene with an N‐indolyl alkylidene β‐amide ester to form a donor–acceptor cyclobutane intermediate, which subsequently undergoes an intramolecular ring‐opening cyclization. Azepine

  据报道催化合成[5 + 2]环加成反应的方法合成了zepino [1,2- a ]吲哚的非对映选择性。该反应大概是通过路易斯酸催化的烯烃与N-吲哚基亚烷基β-酰胺酯的正式[2 + 2]环加成反应形成供体-受体环丁烷中间体，随后进行分子内开环环化反应。形成的ze庚因产物的最高非对映选择性（高达34：1 dr）具有高达92％的收率。
• Catalytic Diastereoselective [5 + 2] Annulation of <i>N</i>-Acryloyl Indoles with Cyclic Sulfonyl Enamides: Facile Access to Isoeburnamonine
  作者：Song Wei、Long Zheng、Sunewang R. Wang、Yong Tang

  DOI：10.1021/acs.orglett.9b04556

  日期：2020.2.7

  ZnBr2-catalyzed stereoselective [5 + 2] annulation of N-acryloyl indoles with cyclic sulfonyl enamides is reported, providing a concise and efficient synthesis of isoeburnamonine, which is the key intermediate for norvincamine. Both [2 + 2] and [4 + 2] cycloadducts, depending on the ring size of the enamides, have been shown to be the important intermediates for this [5 + 2] annulation.