ethyl α-acetyl-(1-methylindol-3-yl)-3-propanoate | 1217886-61-7

• 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: ethyl α-acetyl-(1-methylindol-3-yl)-3-propanoate
• 英文别名: ethyl 2-((1-methyl-1H-indol-3-yl)methyl)-3-oxobutanoate；Ethyl 2-[(1-methylindol-3-yl)methyl]-3-oxobutanoate；ethyl 2-[(1-methylindol-3-yl)methyl]-3-oxobutanoate
• CAS: 1217886-61-7
• 化学式: C₁₆H₁₉NO₃
• 分子量: 273.332
• InChiKey: DOFBEYKJFSABMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  48.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基乙酰乙酸乙酯 、 1-甲基吲哚 在 过氧化苯甲酸叔丁酯 、 palladium(II) trifluoroacetate 、 溶剂黄146 作用下， 以 异丙醇 为溶剂， 反应 22.08h， 以54%的产率得到ethyl α-acetyl-(1-methylindol-3-yl)-3-propanoate
  参考文献：
  名称：

  Palladium-Catalyzed Dehydrogenative β′-Functionalization of β-Keto Esters with Indoles at Room Temperature

  摘要：

  The dehydrogenative beta'-functionalization of a-substituted beta-keto esters with indoles proceeds with high regioselectivities (C3-selective for the indole partner and beta'-selective for the beta-keto ester) and good yields under mild palladium catalysis at room temperature with a variety of oxidants. Two possible mechanisms involving either late or early involvement of indole are presented.

  DOI：

  10.1021/ja300684r

文献信息

• Catalyst-free aqueous multicomponent domino reactions from formaldehyde and 1,3-dicarbonyl derivatives
  作者：Yanlong Gu、Rodolphe De Sousa、Gilles Frapper、Christian Bachmann、Joël Barrault、François Jérôme

  DOI：10.1039/b913846c

  日期：——

  Here we report a catalyst-free aqueous multicomponent domino reaction (MCR) capable of affording a wide range of valuable dihydropyran derivatives from simple, cheap and readily available reactants such as formaldehyde, 1,3-dicarbonyl derivatives, styrene, indole and aniline derivatives. Within the framework of green chemistry, these MCRs gather many advantages such as (i) utilization of water as a solvent, (ii) creation of up to six bonds in one sequence, (iii) 100% of carbon economy and (iv) water as a sole waste. These MCRs exhibit a broad substrate scope and open access to valuable chemicals traditionally produced through multistep processes involving catalysts or organic solvents. More generally, this work opens a new way for creating molecular complexity with maximum simplicity.

  在此，我们报告了一种无催化剂水基多组分多米诺反应（MCR），该反应能够从简单、廉价且容易获得的反应物（如甲醛、1,3-二羰基衍生物、苯乙烯、吲哚和苯胺衍生物）中获得多种有价值的二氢吡喃衍生物。在绿色化学的框架内，这些多重催化还原反应具有许多优点，例如：(i) 利用水作为溶剂；(ii) 在一个序列中生成多达六个键；(iii) 100% 的碳经济性；(iv) 水是唯一的废物。这些 MCR 具有广泛的底物范围，为传统上通过涉及催化剂或有机溶剂的多步工艺生产的有价值化学品开辟了途径。更广泛地说，这项工作为以最简单的方式创造复杂的分子开辟了一条新途径。
• Palladium-Catalyzed Dehydrogenative β′-Functionalization of β-Keto Esters with Indoles at Room Temperature
  作者：Mikko V. Leskinen、Kai-Tai Yip、Arto Valkonen、Petri M. Pihko

  DOI：10.1021/ja300684r

  日期：2012.4.4

  The dehydrogenative beta'-functionalization of a-substituted beta-keto esters with indoles proceeds with high regioselectivities (C3-selective for the indole partner and beta'-selective for the beta-keto ester) and good yields under mild palladium catalysis at room temperature with a variety of oxidants. Two possible mechanisms involving either late or early involvement of indole are presented.