3-(二甲氨基)-1-萘-2-基丙烷-1-酮 | 2752-87-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 3-(二甲氨基)-1-萘-2-基丙烷-1-酮
• 中文别名: 3-(二甲基氨基)-1-(2-萘)-1-丙酮
• 英文名称: 3-(dimethylamino)-1-(naphthalen-2-yl)propan-1-one
• 英文别名: 3-(dimethylamino)-1-naphthalen-2-ylpropan-1-one
• CAS: 2752-87-6
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: WZIOJYCFLAYASE-UHFFFAOYSA-N

物化性质

• 沸点：
  368.7±25.0 °C(Predicted)
• 密度：
  1.072±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(二甲氨基)-1-萘-2-基丙烷-1-酮 在 盐酸 、 lithium aluminium tetrahydride 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 108.0h， 生成 3-dimethylamino-1-(2-naphthyl)propanamine
  参考文献：
  名称：

  Design, parallel synthesis and SAR of novel urotensin II receptor agonists

  摘要：

  A 30-membered library of amides based on the potent urotensin II (UII) receptor agonist FL104, has been synthesized from ten different carboxylic acids and three amines. A synthetic protocol producing the amides in 47-98% yield has been developed in which the purification involved only extractions and in a few cases filtration through an ion-exchange resin. It was found that 5 mg of starting material was enough to obtain reproducible results and excellent purities. Thus, the procedure is estimated to be transferable to fully automated systems. The synthesized compounds were evaluated for their Ull receptor agonistic activities using a cell-based assay (R-SAT). The most active compounds were the 4-trifluoromethylcinnamic amides of 1-(4-chlorophenyt)-3-dimethylamino-propylamine and 1-(2-naphthyl)-3-dimethylamino-propylamine, both showed EC50 values of 130 nM. (c) 2006 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2006.09.015
• 作为产物：
  描述：

  1-(萘-2-基)丙-2-炔-1-醇 在 manganese(IV) oxide 、 频那醇硼烷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 3-(二甲氨基)-1-萘-2-基丙烷-1-酮
  参考文献：
  名称：

  炔酮还原加氢胺化无金属合成β-氨基酮

  摘要：

  本研究描述了一种在非常温和的无金属条件下通过炔烃的还原加氢胺化合成 β-氨基酮的级联方法。它允许炔酮和胺快速转化为相应的β-氨基酮，具有广泛的底物范围和多种功能。这种简单易行的反应过程可成功应用于普罗克生和普罗哌卡因的合成，为合成具有β-氨基酮骨架的药物分子提供了潜在的选择。

  DOI：

  10.1039/d2cc00169a

文献信息

• Synthesis of 2-methoxy-3-(thiophen-2-ylmethyl)quinoline containing amino carbinols as antitubercular agents
  作者：Bidhu Bhusan Karkara、Shashank Shekhar Mishra、Bhupendra N. Singh、Gautam Panda

  DOI：10.1016/j.bioorg.2020.103775

  日期：2020.6

  We have designed and synthesized 2-methoxy-3-(thiophen-2-ylmethyl)quinoline containing amino carbinols as possible anti-tubercular agents to combat the disease. These molecules were synthesized by tethering amino ether linkage with hydroxyl group to diarylquinoline skeleton; hydroxyl and amine chains were engrafted on diaryl ring. They were evaluated against strain (H37Ra) of Mycobacterium tuberculosis

  我们设计并合成了含有2-氨基甲氧基-3-（噻吩-2-基甲基）喹啉的氨基甲醇作为抗结核药，以对抗这种疾病。这些分子是通过将带有羟基的氨基醚键束缚到二芳基喹啉骨架上而合成的。羟基和胺链接枝在二芳基环上。对它们进行了针对结核分枝杆菌菌株（H37Ra）的评估，大多数化合物均具有体外抗结核活性。具有二芳基喹啉羟基氨基醚支架的两种化合物和具有二芳基氨基烷基甲醇核心的三种化合物在6.25μg/ mL下显示出活性。这项研究探索了二芳基甲醇原型作为抗结核分枝杆菌的抑制剂。
• SMALL MOLECULE CMKLR1 ANTAGONISTS IN INFLAMMATORY DISEASE
  申请人：The Board of Trustees of the Leland Stanford Junior University

  公开号：US20200345661A1

  公开（公告）日：2020-11-05

  α-NETA analogs are provided for the treatment of inflammatory disease.

  α-NETA类似物用于治疗炎症性疾病。
• Design of tRNA^Lys₃Ligands: Fragment Evolution and Linker Selection Guided by NMR Spectroscopy
  作者：Florence Chung、Carine Tisné、Thomas Lecourt、Bili Seijo、Frédéric Dardel、Laurent Micouin

  DOI：10.1002/chem.200802451

  日期：2009.7.20

  A fragment‐based approach for the synthesis of ligands of tRNALys3, the HIV reverse‐transcription primer, is described. The use of NMR spectroscopy has proved to be very useful in this approach, not only to detect low‐affinity complexes between small compounds and RNA, but also to provide information on their binding mode and on the way they can be connected. This NMR‐spectroscopy‐guided analysis enabled

  描述了一种基于片段的合成tRNA Lys 3（HIV逆转录引物）配体的方法。事实证明，在这种方法中使用NMR光谱非常有用，不仅可以检测小化合物和RNA之间的低亲和力复合物，还可以提供有关其结合方式和连接方式的信息。这项由NMR光谱引导的分析使我们能够在毫摩尔片段与适当连接子的优化和连接后，设计微摩尔配体。接头区域对结合亲和力和选择性的影响概述了在这种方法中具有与各种接头的灵活组装策略的重要性。
• [EN] UROTENSIN II RECEPTOR MODULATORS<br/>[FR] MODULATEURS DU RECEPTEUR DE L'UROTENSINE II
  申请人：ACADIA PHARM INC

  公开号：WO2003104216A1

  公开（公告）日：2003-12-18

  Disclosed are compounds of Formula I, or salts or prodrugs thereof, complexed with a human urotensin II receptor as defined herein. Also disclosed are compounds of Formula II, or salts or prodrugs thereof, as defined herein. Also disclosed are methods of modulating the activity of a urotensin II receptor using a compound of Formula I, or a compound of Formula II, or salts or prodrugs thereof. In addition, methods of treating diseases related to the activity of urotensin II receptors are disclosed.

  本文披露了根据本文所定义的与人类尿嘧啶 II 受体形成络合物的 Formula I 化合物，或其盐或前药。还披露了根据本文所定义的 Formula II 化合物，或其盐或前药。还披露了使用 Formula I 化合物、Formula II 化合物、或其盐或前药来调节尿嘧啶 II 受体活性的方法。此外，还披露了治疗与尿嘧啶 II 受体活性相关疾病的方法。
• Catalytic Conversion of N-Heteroaromatics to Functionalized Arylamines by Merging Hydrogen Transfer and Selective Coupling
  作者：Zhenda Tan、Chenggang Ci、Jian Yang、Yang Wu、Liang Cao、Huanfeng Jiang、Min Zhang

  DOI：10.1021/acscatal.0c00394

  日期：2020.5.1

  reactive N-heteroaromatics to useful frameworks. Here, by a strategy merging hydrogen transfer and selective coupling, we present a ruthenium-catalyzed deconstruction of N-heteroaromatics to functionalized arylamines with 2-aminoaryl methanols. The reaction is achieved via sequential functionalization of the β and α sites of the initially formed N-heteroarenium salts followed by a C–N cleavage, which proceeds

  迄今为止，尽管在N-杂芳基C–H官能化方面已取得了巨大进展，但在将广泛应用但反应性差的N-杂芳族化合物解构为有用的骨架方面，仍然存在重大的未解决挑战。在这里，通过结合氢转移和选择性偶联的策略，我们提出了钌催化的N-杂芳烃与2-氨基芳基甲醇的官能化芳胺的解构。该反应是通过依次形成最初形成的N-杂芳烃盐的β和α位点进行官能化，然后进行C–N裂解而实现的，其特征是具有广泛的底物范围，出色的官能团耐受性，高化学选择性和原子效率，并适合简化某些生物医学分子的合成。