1-(m-methylphenyl)-1-cyanoacetone | 38377-59-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(m-methylphenyl)-1-cyanoacetone
• 英文别名: 2-(m-tolyl)-3-oxobutanenitrile；2-(3-methylphenyl)-3-oxobutanenitrile；α-Acetyl-3-methylphenylacetonitrile；2-m-tolyl-acetoacetonitrile
• CAS: 38377-59-2
• 化学式: C₁₁H₁₁NO
• 分子量: 173.214
• InChiKey: VTMXXWNCTGJYOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(m-methylphenyl)-1-cyanoacetone 在 盐酸肼 作用下， 以 乙醇 为溶剂， 以85%的产率得到5-methyl-4-(3-methylphenyl)-1H-pyrazol-3-amine
  参考文献：
  名称：

  N-Acetyl-3-aminopyrazoles block the non-canonical NF-kB cascade by selectively inhibiting NIK

  摘要：

  由于击中导向优化，氨基吡唑3a是一种选择性超过44种激酶的NIK抑制剂。

  DOI：

  10.1039/c8md00068a
• 作为产物：
  描述：

  5-methyl-4-m-tolyl-isoxazole 在 乙醇 、 sodium ethanolate 作用下， 生成 1-(m-methylphenyl)-1-cyanoacetone
  参考文献：
  名称：

  Yasuda, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1959, vol. 79, p. 623,626

  摘要：

  DOI：

文献信息

• Metal‐free ring opening of 5‐amino‐1, <scp> 4‐diaryl‐1 <i>H</i> </scp> ‐pyrazoles: A facile access to 2‐aryl‐3‐arylazoacrylonitriles
  作者：Arpita Chatterjee、Divya Radhakrishnan、Debashruti Bandyopadhyay、Selvaraj Kanchithalaivan、Saravanan Peruncheralathan

  DOI：10.1002/jhet.4439

  日期：2022.6

  2-aryl-3-arylazoacrylonitriles are synthesized while attempting the intramolecular N-arylation of 5-aminopyrazoles, using the hypervalent iodine reagent. The synthesis involves phenyl iodine diacetate-assisted ring opening of 5-aminopyrazoles at room temperature. A plausible mechanism for the formation of azoalkenes is proposed.

  在尝试使用高价碘试剂对 5-氨基吡唑进行分子内N-芳基化的同时，合成了各种 2-芳基-3-芳基偶氮丙烯腈。该合成涉及苯基碘二乙酸酯在室温下辅助 5-氨基吡唑的开环。提出了形成偶氮烯烃的合理机制。
• Copper-catalysed <i>N</i>-arylation of 5-aminopyrazoles: a simple route to pyrazolo[3,4-<i>b</i>]indoles
  作者：Arpita Chatterjee、Chudamani Murmu、S. Peruncheralathan

  DOI：10.1039/d0ob00812e

  日期：——

  A copper-catalysed intramolecular N-arylation of 5-aminopyrazoles is demonstrated for the first time. Highly substituted pyrazolo[3,4-b]indoles are synthesized. In particular, the indole core is decorated with halogens and alkyl and methoxy groups. Furthermore, a selective N-arylation of unsymmetrical diaryl bromide containing pyrazoles is exemplified, resulting in valuable pyrazolo[1,5-a]benzimidazoles

  首次证明了铜催化的5-氨基吡唑的分子内N-芳基化。合成了高度取代的吡唑并[3，4- b ]吲哚。特别地，吲哚核被卤素以及烷基和甲氧基装饰。此外，举例说明了含不对称二芳基溴的吡唑的选择性N-芳基化，得到了有价值的吡唑并[1，5- a ]苯并咪唑。
• Synthesis of Vinyl Cyclopropanes via Anion Relay Cyclization
  作者：Kevin M. Allegre、Nathan Brennan、Jon A. Tunge

  DOI：10.1021/acs.orglett.8b01566

  日期：2018.7.20

  A method where an allyl alcohol is formed from a Tsuji–Trost allylation between a vinyl epoxide and an acyl containing nucleophile is described. Subsequently, a retro-Claisen condensation is utilized as a means of through-space anion relay. The anion relay results in the formation of a reactive carbanion and simultaneously activates an allylic alcohol toward intramolecular Tsuji–Trost cyclopropanation

  描述了一种方法，其中烯丙基醇由乙烯基环氧化物和含酰基亲核试剂之间的Tsuji-Trost烯丙基化反应形成。随后，逆向克莱森缩合被用作通过空间阴离子中继的手段。阴离子中继导致反应性碳负离子的形成，并同时使烯丙基醇向分子内Tsuji-Trost环丙烷化。因此，在一个锅中，使用温和且操作简单的程序，将Tsuji-Trost烯丙基化，retro-Claisen活化和Tsuji-Trost环丙烷化相结合，可从环氧乙烷中获得合成有用的乙烯基环丙烷。
• Rhodium‐Catalyzed Asymmetric Hydrogenation of Tetrasubstituted α,β‐Unsaturated Amides: Efficient Access to Chiral β‐Amino Amides†
  作者：Bing Jiao、Fangyuan Wang、Hui Lv

  DOI：10.1002/cjoc.202400344

  日期：2024.11

  The first asymmetric hydrogenation of acyclic tetrasubstituted α,β-unsaturated amides has been achieved by using Rh/DuanPhos complex as a catalyst, delivering chiral β-amino amides with two contiguous chiral centers in excellent yields and high enantioselectivities (up to 99% yield, 96% ee), which provides efficient and concise access to valuable β-amino amide derivatives. The gram-scale reaction and

  通过使用 Rh/DuanPhos 络合物作为催化剂，首次实现了无环四取代 α,β-不饱和酰胺的不对称氢化，以优异的产率和高对映选择性（产率高达 99%， 96% ee)，提供了高效、简洁地获取有价值的 β-氨基酰胺衍生物的方法。克级反应以及β-氨基酰胺向β-氨基酸和β-氨基氰化物的有效转化证明了该方法的实用性。
• Human carbonic anhydrase inhibitory profile of mono- and bis-sulfonamides synthesized via a direct sulfochlorination of 3- and 4-(hetero)arylisoxazol-5-amine scaffolds
  作者：Mikhail Krasavin、Mikhail Korsakov、Zhanna Zvonaryova、Evgenii Semyonychev、Tiziano Tuccinardi、Stanislav Kalinin、Muhammet Tanç、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2017.02.018

  日期：2017.3

  Three distinct series of isoxazole-based primary mono- and bis-sulfonamides have been synthesized via direct sulfochlorination, each of them delivering nanomolar inhibitors of human carbonic anhydrase. Certain pronounced SAR trends have been established and rationalized by in silico docking. These findings expand the structure-activity knowledge base for heterocycle-containing sulfonamide carbonic anhydrase inhibitors and further validate the power of direct electrophilic sulfochlorination as a means of introducing the pharmacophoric primary sulfonamide group into structurally diverse aromatic precursors. (C) 2017 Elsevier Ltd. All rights reserved.