1-(2-氨基-4,5-二甲基苯基)乙酮 | 106634-67-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2-氨基-4,5-二甲基苯基)乙酮
• 中文别名: 乙酮,1-(2-氨基-4,5-二甲基苯基)-(9CI)
• 英文名称: 2-amino-4,5-dimethyl acetophenone
• 英文别名: 1-(2-amino-4,5-dimethylphenyl)ethanone；2-acetyl-4,5-dimethylaniline；1-(2-amino-4,5-dimethyl-phenyl)-ethanone；1-(2-Amino-4,5-dimethyl-phenyl)-aethanon；2-amino-4,5-dimethylacetophenone；2-Amino-4.5-dimethyl-acetophenon
• CAS: 106634-67-7
• 化学式: C₁₀H₁₃NO
• mdl: MFCD20542811
• 分子量: 163.219
• InChiKey: BAXIUKDACWCIEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-氨基-4,5-二甲基苯基)乙酮 生成 1-[4,5-dimethyl-2-(2-nitro-ethylidenamino)-phenyl]-ethanone
  参考文献：
  名称：

  CHU C. K.; BARDOS T. J., J. HETEROCYCL. CHEM. , 1977, 14, NO 6, 1053-1057

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二甲基苯乙酮 在 palladium 10% on activated carbon 、 氢气 、 硝酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 1-(2-氨基-4,5-二甲基苯基)乙酮
  参考文献：
  名称：

  一种6,7-二甲基-4-羟基喹啉的制备方法

  摘要：

  本发明公开了一种6,7‑二甲基‑4‑羟基喹啉的制备方法，以1‑(3,4‑二甲基苯基)乙酮为起始原料，经过硝化、还原、关环得到目标产物，该化合物是重要的医药中间体。

  公开号：

  CN107286090A

文献信息

• THERAPEUTIC COMPOUNDS AND USES THEREOF
  申请人：Kala Pharmaceuticals, Inc.

  公开号：US20140235634A1

  公开（公告）日：2014-08-21

  Described herein are compounds of Formula (I) or Formula (VI), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. Also provided are particles (e.g., nanoparticles) comprising compounds of Formula (I) or Formula (VI) and pharmaceutical compositions thereof that are mucus penetrating. Methods of using the compounds or pharmaceutical compositions thereof for treating diseases are also provided.

  本文描述了公式（I）或公式（VI）的化合物，其药学上可接受的盐以及其药物组合物。还提供了包含公式（I）或公式（VI）化合物及其药物组合物的微粒（例如，纳米颗粒），这些微粒具有穿透黏液的特性。还提供了使用这些化合物或药物组合物治疗疾病的方法。
• Identification of Anthranilic Acid Derivatives as a Novel Class of Allosteric Inhibitors of Hepatitis C NS5B Polymerase
  作者：Thomas Nittoli、Kevin Curran、Shabana Insaf、Martin DiGrandi、Mark Orlowski、Rajiv Chopra、Atul Agarwal、Anita Y. M. Howe、Amar Prashad、M. Brawner Floyd、Bernard Johnson、Alan Sutherland、Karen Wheless、Boris Feld、John O'Connell、Tarek S. Mansour、Jonathan Bloom

  DOI：10.1021/jm061428x

  日期：2007.5.1

  A series of potent anthranilic acid-based inhibitors of the hepatitis C NS5B polymerase has been identified. The inhibitors bind to a site on NS5B between the thumb and palm regions adjacent to the active site as determined by X-ray crystallography of the enzyme-inhibitor complex. Guided by both molecular modeling and traditional SAR, the enzyme activity of the initial hit was improved by approximately

  已鉴定出一系列强效邻氨基苯甲酸丙型肝炎 NS5B 聚合酶抑制剂。通过酶抑制剂复合物的 X 射线晶体学测定，抑制剂与 NS5B 上拇指和手掌区域之间与活性位点相邻的位点结合。在分子建模和传统 SAR 的指导下，初始命中的酶活性提高了约 100 倍，产生了一系列有效且选择性的 NS5B 抑制剂，IC50 值低至 10 nM。这些化合物也是培养的 HUH7 细胞中 HCV 复制子的抑制剂。
• Synthesis of Bridged Benzazocines and Benzoxocines by a Titanium-Catalyzed Double-Reductive Umpolung Strategy
  作者：Plamen Bichovski、Thomas M. Haas、Daniel Kratzert、Jan Streuff

  DOI：10.1002/chem.201405852

  日期：2015.2.2

  A sequence of two titanium(III)‐catalyzed reductive umpolung reactions is reported that allows the rapid construction of benzazo‐ and benzoxozine building blocks. The first step is a reductive cross‐coupling of quinolones or chromones with Michael acceptors. This reaction proceeds with complete syn‐selectivity for the quinolone functionalization while the anti‐diastereomers are obtained as the major

  据报道，由两个钛（III）催化的还原性蛋白还原反应序列可快速构建苯并偶氮和苯并恶嗪结构单元。第一步是喹诺酮或色酮与迈克尔受体的还原性交叉偶联。这种反应完全进行SYN -选择性的喹诺酮类功能化，而抗-diastereomers是从色酮的主要产品获得。在不同的反应条件下，可以改变立体化学结果以提供合成苯并二氢吡喃酮产品。随后的还原性酮基自由基环化以良好的产率锻造了三环标题化合物。提供了解释所观察到的立体选择性的立体化学模型，并且通过X射线分析和2D NMR光谱实验明确验证了产物构型。
• Method for preparing 4-hydroxycinnolines in a pH controlled system
  申请人：Shell Oil Company

  公开号：US04620000A1

  公开（公告）日：1986-10-28

  In the preparation of a 4-hydroxycinnoline wherein the diazonium salt of a 2-aminoacetophenone in aqueous solution is allowed to undergo cyclocondensation, the improvement that comprises maintaining the pH of the solution between about 4.0 and 8.5 during the cyclocondensation.

  在制备4-羟基菲啰啉时，将2-氨基苯乙酮的重氮盐溶解在水溶液中，使其进行环缩反应。改进的方法包括在环缩反应过程中保持溶液的pH值在大约4.0至8.5之间。
• X-ray Structures of 1-Ethynyl-2-Nitrobenzene and 1-Ethynyl-4,5-Dimethyl-2-Nitrobenzene: Correlation to the Enhanced Rate of Hydration and Investigation of the C–H···O Alkyne-Nitro Hydrogen Bonding
  作者：Eric Bosch、Laura Jeffries

  DOI：10.1007/s10870-016-0660-0

  日期：2016.7

  The single crystal X-ray structures of 2-nitrophenylacetylene, 1, and 4,5-dimethyl-2-nitrophenylacetylene, 2, are presented. In both structures the nitro moiety is essentially coplanar with the benzene ring and interacts with the proximal alkyne which is slightly distorted. The crystal packing of both compounds is dominated by intramolecular alkyne-nitro C–H···O hydrogen bonds that are supplemented by weak arene C–H···O (nitro) hydrogen bonds. Compound 1 crystallizes in the monoclinic space group P21/c with a = 3.7874(5), b = 13.0673(16), c = 13.98174(17) Å, β = 90.587(2) and Z = 4. The molecule is disordered over two sites with occupancy ratio of 88:12. Compound 2 crystallizes in the triclinic space group P-1 with a = 7.6080(5), b = 9.8811(6), c = 12.8240(8) Å, α = 108.1760(10), β = 102.4170, γ = 96.6480(10) and Z = 4. The intermolecular interactions in both structures were dominated by alkyne-nitro and arene-nitro C–H···O hydrogen bonds. The structures of 2-nitrophenylacetylene and 4,5-dimethyl-2-nitrophenylacetylene display a strong nitro-alkyne intramolecular O···C interaction resulting in distortion of the alkyne and terminal alkyne-nitro CH···O intermolecular interactions.

  呈现了2-硝基苯乙炔（1）和4,5-二甲基-2-硝基苯乙炔（2）的单晶X射线结构。在这两种结构中，硝基基团基本上与苯环共平面，并与略微扭曲的近端炔烃相互作用。这两种化合物的晶体堆积主要由分子内炔烃-硝基C–H···O氢键主导，同时也有弱的芳香烃C–H···O（硝基）氢键作为补充。化合物1结晶于单斜晶系P21/c空间群，a = 3.7874(5) Å, b = 13.0673(16) Å, c = 13.98174(17) Å，β = 90.587(2)°，Z = 4。该分子在两个位置上无序，占据比例为88:12。化合物2结晶于三斜晶系P-1空间群，a = 7.6080(5) Å, b = 9.8811(6) Å, c = 12.8240(8) Å，α = 108.1760(10)°，β = 102.4170°，γ = 96.6480(10)°，Z = 4。这两种结构中的分子间相互作用主要由炔烃-硝基和芳香烃-硝基C–H···O氢键主导。2-硝基苯乙炔和4,5-二甲基-2-硝基苯乙炔的结构展示了强烈的硝基-炔烃分子内O···C相互作用，导致炔烃的扭曲和末端炔烃-硝基CH···O分子间相互作用。