N-[1-(4-acetylphenyl)ethyl]acetamide | 862658-26-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[1-(4-acetylphenyl)ethyl]acetamide
• CAS: 862658-26-2
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: RZAWAOKACCQVTF-UHFFFAOYSA-N

物化性质

• 沸点：
  415.2±28.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[1-(4-acetylphenyl)ethyl]acetamide 在 sodium hydroxide 、 硫酸 、 溴 作用下， 以 1,4-二氧六环 为溶剂， 生成 (+/-)-N-(4-methoxycarbonylphenylethyl)acetamide
  参考文献：
  名称：

  Novel DMARDs on the basis of a new concept of dual cytokine regulation, TNF-α suppression and IL-10 augmentation

  摘要：

  A series of arylpiperazine derivatives was synthesized to obtain agents showing apparent therapeutic effects in a chronic inflammatory animal model, starting from a lead possessing potent dual cytokine regulatory activity in vivo. We found a pyrimidylpiperazine derivative 17c showing the dual regulatory activity and an excellent therapeutic effect in an adjuvant-induced arthritis model. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00129-3
• 作为产物：
  描述：

  4-乙酰苯基三氟甲烷磺酸酯 在 1,1'-双(二苯基膦)二茂铁 、 Wilkinson's catalyst 、 tris(dibenzylideneacetone)dipalladium (0) 氢气 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 7.75h， 生成 N-[1-(4-acetylphenyl)ethyl]acetamide
  参考文献：
  名称：

  Fast and Regioselective Heck Couplings with N-Acyl-N-vinylamine Derivatives

  摘要：

  Highly regioselective Heck couplings of aryl triflates with N-acyl-N-vinylamines lacking an N-alkyl substituent were achieved with reaction times of approximately 1 h in yields ranging from 62 to 98% using 1.5 mol % of Pd-2(dba)(3), 3 mol % of DPPF, and diethylisopropylamine in dioxane. The efficiency of these cross-couplings were studied with several N-vinylamides and an example each of an N-vinylcarbamate and an N-vinylurea. The Heck coupling products easily underwent acidic hydrolysis to the corresponding aryl methyl ketone or in situ hydrogenation in the presence of (Ph3P)(3)RhCl under a hydrogen atmosphere to provide the N-acyl derivatives of pharmaceutically relevant benzylic amines. The coupling of a vinyl triflate and more interestingly a vinyl tosylate to N-vinyl acetamide was also studied affording a 2-acylamino-1,3-butadiene with the same high regioselectivity in preference for the alpha-isomer. This result suggests that Heck couplings of electron-rich alkenes with vinyl tosylates also follow a cationic pathway.

  DOI：

  10.1021/jo050669u

文献信息

• Piperazine compounds and medicinal use thereof
  申请人：Mitsubishi Pharma Corporation

  公开号：US20030018034A1

  公开（公告）日：2003-01-23

  The present invention relates to a piperazine compound of the formula 1 wherein R 1 and R 2 are each hydrogen, halogen, lower alkyl, lower alkoxy, amino, substituted amino, nitro, hydroxy or cyano, R 3 , R 4 and R 5 are each hydrogen, halogen, lower alkyl, lower alkoxy, nitro, amino, substituted amino or hydroxy, R 6 and R 7 are each hydrogen, lower alkyl, lower alkyl substituted by halogen, aralkyl, acyl or lower acyl substituted by halogen, R 8 and R 9 are each hydrogen or lower alkyl, Y is lower alkylene and the like, and ring A is phenyl, pyrimidyl, thiazolyl, pyridyl, pyrazyl or imidazolyl, a pharmaceutically acceptable salt thereof and pharmaceutical agents containing these compounds. The compound of the present invention has superior TNF-&agr; production inhibitory effect and/or IL-10 production promoting effect, and, since it is free of or shows only strikingly reduced expression of an effect on the central nervous system, the compound is useful as a highly safe and superior TNF-&agr; production inhibitor an/or IL-10 production promoter and is useful as an agent for the prophylaxis or treatment of various diseases caused by abnormal TNF-&agr; production, diseases curable with IL-10, such as chronic inflammatory diseases, acute inflammatory diseases, inflammatory diseases due to infection, autoimmune diseases, allergic diseases, and TNF-&agr; mediated diseases.

  本发明涉及一种哌嗪化合物，其化学式为1，其中R1和R2分别为氢、卤素、低碳基、低氧基、氨基、取代氨基、硝基、羟基或氰基，R3、R4和R5分别为氢、卤素、低碳基、低氧基、硝基、氨基、取代氨基或羟基，R6和R7分别为氢、低碳基、被卤素取代的低碳基、芳基烷基、酰基或被卤素取代的低酰基，R8和R9分别为氢或低碳基，Y为低碳基亚烷基等，环A为苯基、嘧啶基、噻唑基、吡啶基、吡唑基或咪唑基，以及其药学上可接受的盐和含有这些化合物的药物制剂。本发明的化合物具有优异的TNF-α产生抑制作用和/或IL-10产生促进作用，并且由于其不具有或仅表现出对中枢神经系统的作用明显降低，因此该化合物可用作高度安全和优越的TNF-α产生抑制剂和/或IL-10产生促进剂，并可用作预防或治疗由异常TNF-α产生引起的各种疾病、可用IL-10治愈的疾病，例如慢性炎症性疾病、急性炎症性疾病、由感染引起的炎症性疾病、自身免疫性疾病、过敏性疾病和TNF-α介导的疾病。
• Electrochemical Benzylic C(sp3)–H Amidation via Ritter-Type Reaction in the Absence of External Mediator and Oxidant
  作者：Ping Liu、Peipei Sun、Qiao Chu、Yeqin Zhou、Ce Ji

  DOI：10.1055/a-1992-7066

  日期：——

  alkylarenes in the absence of external mediator and oxidant is described. This direct benzylic C(sp3)–H amidation utilizes cheap CH3CN or other nitriles as the nitrogen source and trace amount of H2O in the solvent as the oxygen and hydrogen source. A wide range of alkylarenes were found to be compatible, providing a variety of N-benzyl-substituted amides in moderate to good yields.

  描述了一种简单的方法，涉及在没有外部介质和氧化剂的情况下烷基芳烃的电化学里特型酰胺化。这种直接苄基 C(sp3)–H 酰胺化利用廉价的 CH3CN 或其他腈作为氮源，溶剂中的痕量 H2O 作为氧和氢源。发现范围广泛的烷基芳烃是相容的，以中等到良好的收率提供各种 N- 苄基取代的酰胺。
• Electrochemical Oxidative C–H Amination through a Ritter-Type Reaction
  作者：Yiwen Xu、Qiang Li、Runyou Ye、Buyi Xu、Xiangge Zhou

  DOI：10.1021/acs.joc.3c00609

  日期：2023.7.7

  A straightforward strategy for direct benzylic C–H bond amination via an electrochemical Ritter-type reaction is developed. The reaction demonstrates simpler and milder reaction conditions over the existing methods without extra mediator. Moderate to excellent yields up to 94% of the desired amide products were obtained with a broad substrate scope. The removal of the Ac group by a simple step can

  开发了一种通过电化学 Ritter 型反应直接进行苄基 C-H 键胺化的简单策略。该反应比现有方法表现出更简单、更温和的反应条件，无需额外的介体。在广泛的底物范围内获得了中等至优异的收率，高达 94% 的所需酰胺产物。通过简单的步骤去除Ac基团可以得到不含NH的苄胺，为生物活性分子的后期功能化提供了合适的方法。
• 4-AMINO(ALKYL)CYCLOHEXANE-1-CARBOXAMIDE COMPOUND AND USE THEREOF
  申请人：YOSHITOMI PHARMACEUTICAL INDUSTRIES, LTD.

  公开号：EP0641781A1

  公开（公告）日：1995-03-08

  A 4-amino(alkyl)cyclohexane-1-carboxamide compound represented by general formula (I), an isomer thereof, and a pharmaceutically acceptable acid addition salt thereof, wherein each symbol is as defined in the specification. These substances have a remarkable, highly persistent and lowly toxic activity of increasing blood stream in coronary, cerebral, renal and peripheral arteries, and are useful as a potent and persistent hypotensive and a drug for preventing and treating diseases of a cardiovascular system such as coronary, cerebral, renal and peripheral arteries. Furthermore, they are useful as an antasthmatic, because they have activities of inhibiting experimental guinea pig asthma caused by the inhalation of histamine and inhibiting contraction of a specimen of an extirpated guinea pig trachea caused by acetylcholine.

  一种由通式(I)代表的 4-氨基(烷基)环己烷-1-甲酰胺化合物、其异构体及其药学上可接受的酸加成盐，其中各符号如说明书中所定义。这些物质在增加冠状动脉、脑动脉、肾动脉和外周动脉血流方面具有显著、高持久性和低毒性的活性，可用作强效持久的降压药以及预防和治疗冠状动脉、脑动脉、肾动脉和外周动脉等心血管系统疾病的药物。此外，它们还可用作抗哮喘药，因为它们具有抑制由吸入组胺引起的实验性豚鼠哮喘和抑制由乙酰胆碱引起的已切除豚鼠气管标本收缩的活性。
• PIPERAZINE COMPOUNDS AND MEDICINAL USE THEREOF
  申请人：YOSHITOMI PHARMACEUTICAL INDUSTRIES, LTD.

  公开号：EP1029851A1

  公开（公告）日：2000-08-23

  Piperazine compounds represented by the following general formula (I) or pharmaceutically acceptable salts thereof and drugs comprising these compounds, wherein R1 and R2 represent each hydrogen, halogeno, lower alkyl, lower alkoxy, optionally substituted amino, nitro, hydroxy or cyano; R3, R4 and R5 represent each hydrogen, halogeno, lower alkyl, lower alkoxy, nitro, optionally substituted amino or hydroxy; R6 and R7 represent each hydrogen, optionally halogenated lower alkyl, aralkyl, acyl or halogenated lower acyl; R8 and R9 represent each hydrogen or lower alkyl; Y represents lower alkylene, etc.; and the ring A represents phenyl, pyrimidyl, thiazolyl, pyridyl, pyrazyl or imidazolyl. Because of having excellent TNF-α production inhibitory effect and/or IL-10 production promoting effect, these compounds are useful as TNF-α production inhibitors and/or IL-10 production promoters with high safety. They are useful as preventives or remedies for, e.g., chronic inflammatory diseases, acute inflammatory diseases, inflammatory diseases caused by infection, autoimmune diseases, allergic diseases and other TNF-α-mediated diseases.

  由以下通式(I)代表的哌嗪化合物或其药学上可接受的盐以及包含这些化合物的药物，其中 R1 和 R2 分别代表氢、卤素、低级烷基、低级烷氧基、任选取代的氨基、硝基、羟基或氰基；R3、R4 和 R5 分别代表氢、卤素、低级烷基、低级烷氧基、硝基、任选取代的氨基或羟基； R6 和 R7 分别代表氢、任选卤代低级烷基、芳基、酰基或卤代低级酰基； R8 和 R9 分别代表氢或低级烷基； Y 代表低级亚烷基等。环 A 代表苯基、嘧啶基、噻唑基、吡啶基、吡嗪基或咪唑基。由于这些化合物具有优异的 TNF-α 生成抑制作用和/或 IL-10 生成促进作用，因此可用作 TNF-α 生成抑制剂和/或 IL-10 生成促进剂，安全性高。它们可用于预防或治疗慢性炎症性疾病、急性炎症性疾病、感染引起的炎症性疾病、自身免疫性疾病、过敏性疾病和其他TNF-α介导的疾病。