2-乙酰基苯基乙腈 | 58422-85-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-乙酰基苯基乙腈
• 英文名称: o-acetylphenylacetonitrile
• 英文别名: (2-acetyl-phenyl)-acetonitrile；2-Acetylphenylacetonitrile；2-(2-acetylphenyl)acetonitrile
• CAS: 58422-85-8
• 化学式: C₁₀H₉NO
• mdl: MFCD22414269
• 分子量: 159.188
• InChiKey: QDISFSKYAUGJBK-UHFFFAOYSA-N

物化性质

• 沸点：
  116 °C(Press: 0.2 Torr)
• 密度：
  1.081

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  2-乙酰基苯基乙腈 在 N-甲基咪唑 作用下， 以 甲醇 为溶剂， 生成 3-oxo-indan-1-carbonitrile
  参考文献：
  名称：

  Photochemical Preparation of Highly Functionalized 1-Indanones

  摘要：

  A series of o-alkylphenyl alkyl ketones I were synthesized by different methods. The presence of a leaving group X adjacent to the carbonyl group is the special peculiarity of these ketones. Upon irradiation the keto carbonyl group of these compounds undergoes an n-pi* excitation followed by a 1,5-hydrogen migration from the o-alkyl substituent to the carbonyl oxygen atom. The thus formed 1,4-diradicals are subject to a very rapid elimination of acid HX, giving 1,5-diradicals. We called this process spin center shift. After intersystem crossing these diradicals cyclize to 1-indanones 20 in good yields. Depending on the solvent and on substituents, o-alkoxyalkyl ketones 22 or benzo[c]furanes 21 are obtained as byproducts. The mechanism of the cyclization was elucidated by quantum chemical calculations and kinetic measurements.

  DOI：

  10.1021/jo040173x
• 作为产物：
  描述：

  [2-(2-methyl-[1,3]dioxolan-2-yl)-phenyl]-acetonitrile 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以95%的产率得到2-乙酰基苯基乙腈
  参考文献：
  名称：

  Photochemical Preparation of Highly Functionalized 1-Indanones

  摘要：

  A series of o-alkylphenyl alkyl ketones I were synthesized by different methods. The presence of a leaving group X adjacent to the carbonyl group is the special peculiarity of these ketones. Upon irradiation the keto carbonyl group of these compounds undergoes an n-pi* excitation followed by a 1,5-hydrogen migration from the o-alkyl substituent to the carbonyl oxygen atom. The thus formed 1,4-diradicals are subject to a very rapid elimination of acid HX, giving 1,5-diradicals. We called this process spin center shift. After intersystem crossing these diradicals cyclize to 1-indanones 20 in good yields. Depending on the solvent and on substituents, o-alkoxyalkyl ketones 22 or benzo[c]furanes 21 are obtained as byproducts. The mechanism of the cyclization was elucidated by quantum chemical calculations and kinetic measurements.

  DOI：

  10.1021/jo040173x

文献信息

• [EN] 3,9-DIAZASPIRO[5.5]UNDECANE COMPOUNDS<br/>[FR] COMPOSÉS DE 3,9-DIAZASPIRO[5.5]UNDÉCANE
  申请人：BAYER AG

  公开号：WO2020048829A1

  公开（公告）日：2020-03-12

  The present invention covers 3,9-diazaspiro[5.5]undecane compounds of general formula (I) and general formula (I-a), in which R1, R2, R3 and R4 are as defined herein, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds and the use of said compounds for manufacturing pharmaceutical compositions for the treatment and/or prophylaxis of diseases, in particular of hyperproliferative disorders, as a sole agent or in combination with other active ingredients.

  本发明涵盖了一般式(I)和一般式(I-a)的3,9-二氮杂螺[5.5]十一烷化合物，其中R1、R2、R3和R4如本文所定义，制备所述化合物的方法，用于制备所述化合物的中间化合物，包含所述化合物的药物组合物和组合物，以及利用所述化合物制造用于治疗和/或预防疾病的药物组合物，特别是治疗过度增殖性疾病，作为唯一药剂或与其他活性成分组合使用。
• Microwave-Assisted One-Step Synthesis of Acetophenones<i>via</i>Palladium-Catalyzed Regioselective Arylation of Vinyloxytrimethylsilane
  作者：Wangke Qian、Lei Zhang、Haifeng Sun、Hualiang Jiang、Hong Liu

  DOI：10.1002/adsc.201200334

  日期：2012.11.26

  ether, the arylating agent and the catalytic system. In this study, an effective and practical method was successfully developed for the synthesis of acetophenones with high regioselectivity under palladium-catalyzed conditions. A variety of acetophenones was readily prepared from aryl iodides in good to excellent yields under microwave irradiation in a single step. The key feature of our new protocol

  烯醇醚的钯介导的芳基化（Heck芳基化）的区域化学对烯醇醚，芳基化剂和催化体系的结构敏感。在这项研究中，成功​​地开发了一种有效且实用的方法，用于在钯催化的条件下合成具有高区域选择性的苯乙酮。在微波辐射下，一步就可以从芳基碘化物容易地制得各种苯乙酮，收率好至极好。我们新协议的关键特征是使用乙烯基氧基三甲基硅烷作为高度区域选择性酰化试剂。
• A Continuous Flow Solution to Achieving Efficient Aerobic Anti-Markovnikov Wacker Oxidation
  作者：S. L. Bourne、S. V. Ley

  DOI：10.1002/adsc.201300278

  日期：2013.7.8

  An aerobic anti‐Markovnikov Wacker oxidation for the flow‐synthesis of arylacetaldehydes is reported. In the process, flow chemistry techniques have provided a means to control and minimise the over‐oxidation of sensitive products. The reaction showed general applicability to various functionalised styrenes and provided a process capable of a multi‐gram scale.

  据报道，用于芳基乙醛流动合成的好氧抗马尔科夫尼科夫·瓦克氧化反应。在此过程中，流化学技术提供了一种控制和最小化敏感产品过度氧化的方法。该反应显示出对各种官能化苯乙烯的普遍适用性，并提供了可达到数克规模的工艺。
• P&lt;sub&gt;2&lt;/sub&gt;O&lt;sub&gt;5&lt;/sub&gt;/SiO&lt;sub&gt;2&lt;/sub&gt; : A Simple and Effective Catalyst for the Synthesis of Nsubstituted 1-Alkyl and 1-Aryl 3-Aminoisoquinolines
  作者：Leticia J. Méndez、Alicia S. Cánepa、Ruben Rimada、Rodolfo D. Bravo

  DOI：10.2174/1570178611310040003

  日期：2013.5.1

  A synthesis of N-substituted 1-alkyl and 1-aryl 3-aminoisoquinolines by cyclocondensation of 2- acylphenylacetonitriles with aliphatic and aromatic amines using P2O5/SiO2 as catalysts is described. Selectivity, simplicity of operation and easy work-up are some advantages of this method.

  描述了一种通过将2-酰基苯乙腈与脂肪族和芳香族胺进行环缩合，使用P2O5/SiO2作为催化剂合成N取代的1-烷基和1-芳基3-氨基异喹啉的方法。该方法的优点包括选择性好、操作简单和易于后处理。
• Microwave-induced Synthesis of N-Substituted 1-Alkyl and 1-Aryl 3-Aminoisoquinolines
  作者：Leticia Mendez、Maria Villalba、Alicia Canepa、Rodolfo Bravo

  DOI：10.2174/1570178614666161216101410

  日期：2017.2.13

  antimalaric, anticonvulsant and anti-inflammatory. Although several preparation routes may be found in the literature for the preparation of these compounds, many of these methods present difficulties, including laborious isolation methods, drastic conditions and extended reaction times. Methods: The synthesis of N-substituted 1-alkyl and 1-aryl- 3-aminoisoquinolines is developed through the reaction of 2

  背景：氨基异喹啉是一类重要的杂环化合物。这些化合物具有广泛的药理特性，包括抗疟疾，抗惊厥和抗炎。尽管可以在文献中找到制备这些化合物的几种制备途径，但是这些方法中的许多都存在困难，包括费力的分离方法，苛刻的条件和延长的反应时间。 方法：在微波辐射条件下，通过2-酰基苯基乙腈与胺的反应，开发了N-取代的1-烷基和1-芳基-3-氨基异喹啉。反应在不使用催化剂的乙醇溶剂中进行。平行地，这些反应在相同的温度条件下使用不同量的P 2 O 5 / SiO 2作为催化剂进行。 结果：使用微波辐射合成了一系列N-取代的1-烷基和1-芳基-3-氨基异喹啉，它们具有高的选择性，短的反应时间并且不使用催化剂。在微波辐射条件下使用P2O5 / SiO2作为催化剂对这些反应无效。 结论：结果表明，微波辐射下2-酰基苯基乙腈与胺反应可合成N-取代的1-烷基和1-芳基-3-氨基异喹啉。该方法的一些重要优点包括反应时间大大