1-乙酰基-1H-吲哚-5-甲醛 | 1038864-27-5

• 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
• 中文名称: 1-乙酰基-1H-吲哚-5-甲醛
• 英文名称: 1-acetylindole-5-carboxaldehyde
• 英文别名: 1-acetyl-1H-indole-5-carbaldehyde；1-acetyl-1H-Indole-5-carboxaldehyde；1-acetylindole-5-carbaldehyde
• CAS: 1038864-27-5
• 化学式: C₁₁H₉NO₂
• 分子量: 187.198
• InChiKey: ORUOEULTOMRIMW-UHFFFAOYSA-N

物化性质

• 熔点：
  113-114 °C
• 沸点：
  336.0±15.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  39.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-乙酰基-1H-吲哚-5-甲醛 、 苯 在 silver(I) acetate 、 palladium diacetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 70.0h， 以56%的产率得到1-乙酰基-2-苯基-1H-吲哚-5-甲醛
  参考文献：
  名称：

  Oxidant-controlled regioselectivity in the oxidative arylation of N-acetylindoles

  摘要：

  N-Acetylindoles can be oxidatively coupled with arenes such as benzene or pentafluorobenzene in dioxane. The use of Cu(OAc)(2) as the stoichiometric oxidant produces selective arylation at the 3-position of indole while AgOAc produces selective arylation at indole's 2-position. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.04.073
• 作为产物：
  描述：

  5-吲哚甲醛 、 乙酸酐 在 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以81%的产率得到1-乙酰基-1H-吲哚-5-甲醛
  参考文献：
  名称：

  Oxidant-controlled regioselectivity in the oxidative arylation of N-acetylindoles

  摘要：

  N-Acetylindoles can be oxidatively coupled with arenes such as benzene or pentafluorobenzene in dioxane. The use of Cu(OAc)(2) as the stoichiometric oxidant produces selective arylation at the 3-position of indole while AgOAc produces selective arylation at indole's 2-position. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.04.073

文献信息

• <b>N-Heterocyclic Carbene-Photocatalyzed Tricomponent Regioselective 1,2-Diacylation of Alkenes Illuminates the Mechanistic Details of the Electron Donor–Acceptor Complex-Mediated Radical Relay Processes</b>
  作者：Shengfei Jin、Xianwei Sui、Graham C. Haug、Viet D. Nguyen、Hang T. Dang、Hadi D. Arman、Oleg V. Larionov

  DOI：10.1021/acscatal.1c04594

  日期：2022.1.7

  establishing direct, tricomponent access to 1,4-diketones, key intermediates in heterocyclic and medicinal chemistry. The studies revealed the central role of the electron donor–acceptor complex formed from an N-heterocyclic carbene (NHC) catalyst-derived intermediate and an acyl transfer reagent, providing a detailed description of the structural and electronic factors determining the characteristics of

  光催化反应的发展需要详细了解支持观察到的反应性的机制，但许多光催化系统的机制细节，特别是那些涉及电子供体-受体复合物的系统，仍然难以捉摸。我们在此报告了光催化烯烃 1,2-二酰化的发展以及联合机理和计算研究，该研究能够区域选择性安装两个不同的酰基，建立直接的三组分访问 1,4-二酮，杂环和药物化学中的关键中间体. 研究揭示了由N形成的电子供体 - 受体复合物的核心作用-杂环卡宾 (NHC) 催化剂衍生的中间体和酰基转移试剂，详细描述了决定介导光催化转化的光诱导电荷转移过程特征的结构和电子因素。深入研究还阐明了其他自由基中间体和电子供体在自由基反应中与N-杂环卡宾的催化活性相关的作用。
• 10.1039/d4sc02356k
  作者：Sui, Xianwei、Dang, Hang T.、Porey, Arka、Trevino, Ramon、Das, Arko、Fremin, Seth O.、Hughes, William B.、Thompson, William T.、Dhakal, Shree Krishna、Arman, Hadi D.、Larionov, Oleg V.

  DOI：10.1039/d4sc02356k

  日期：——

  photocatalytic tricomponent decarboxylative radical-mediated amine construction that enables modular access to α-branched secondary amines directly from the broad and structurally diverse chemical space of carboxylic acids in a tricomponent reaction with aldehydes and aromatic amines. Our studies reveal the key role of acridine photocatalysis acting in concert with copper and Brønsted acid catalytic processes

  胺是药物化学和生物化学中的核心重要基序，也是有机合成中不可或缺的中间体和关键。尽管它们具有跨学科的突出地位，但胺的合成仍然依赖于基于有机金属试剂的减少和添加的双电子方法，限制了它们的可利用化学空间，并且需要逐步预组装合成前体。我们在此报道了一种均质光催化三组分脱羧自由基介导的胺结构，该结构能够在与醛和芳香胺的三组分反应中直接从广泛且结构多样的羧酸化学空间模块化获得α-支化仲胺。我们的研究揭示了吖啶光催化与铜和布朗斯台德酸催化过程协同作用在促进以前难以实现的均相光催化反应中的关键作用，并为各种胺和非蛋白性α-氨基酸提供了简化的序列。
• Cu(II)-Catalyzed Direct and Site-Selective Arylation of Indoles Under Mild Conditions
  作者：Robert J. Phipps、Neil P. Grimster、Matthew J. Gaunt

  DOI：10.1021/ja801767s

  日期：2008.7.1

  We have developed a new site-selective Cu(II)-catalyzed C-H bond funtionalization process that can selectively arlate indoles at either the C3 or C2 position under miled conditions. The scope of arylation process is broad and tolerates broad functionality on both indole and aryl unit, which makes it amenable to further elaboartion. The mechanism of the arylation reaction is proposed to proceed via a Cu(III)-aryl that undergoes intial addition at the C3 position of the indole motif. We speculate that site of indole arylation arises through a migration of the Cu(III)-aryl group of C3 to C2, and this can be controlled by the nature of the group on the nitrogen atm; free (NH)-and N-alkylindoles deliver the C3-arylated product, whereas N-acytylindoles affored the C2 isomer, both with excellent yield and selectivity.
• Oxidant-controlled regioselectivity in the oxidative arylation of N-acetylindoles
  作者：Shathaverdhan Potavathri、Ashley S. Dumas、Timothy A. Dwight、Gregory R. Naumiec、Jeffrey M. Hammann、Brenton DeBoef

  DOI：10.1016/j.tetlet.2008.04.073

  日期：2008.6

  N-Acetylindoles can be oxidatively coupled with arenes such as benzene or pentafluorobenzene in dioxane. The use of Cu(OAc)(2) as the stoichiometric oxidant produces selective arylation at the 3-position of indole while AgOAc produces selective arylation at indole's 2-position. (C) 2008 Elsevier Ltd. All rights reserved.