6-acetyl-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-3-one | 26518-72-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 6-acetyl-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-3-one
• 英文别名: 6-acetyl-4-methyl-2H-1,4-benzoxazin-3(4H)-one；6-Acetyl-4-methyl-2H-1,4-benzoxazin-3(4)-one；6-acetyl-4-methyl-4H-benzo[1,4]oxazin-3-one；6-acetyl-4-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one；6-Acetyl-4-methyl-2H-1,4-benzoxazin-3-on；6-acetyl-4-methyl-1,4-benzoxazin-3-one
• CAS: 26518-72-9
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: KARZBZOCCAOBPH-UHFFFAOYSA-N

物化性质

• 熔点：
  142 °C(Solv: hexane (110-54-3))
• 沸点：
  477.6±45.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-acetyl-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-3-one 在 四丁基硫酸氢铵 吡啶 、 sodium hydroxide 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 ethyl 2-[1-(4-methyl-3-oxo-1,4-benzoxazin-6-yl)ethylideneamino]oxyacetate
  参考文献：
  名称：

  Shridhar, D. R.; Sastry, C. V. Reddy; Bansal, O. P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 12, p. 1236 - 1242

  摘要：

  DOI：
• 作为产物：
  描述：

  2H-1,4-苯并噁嗪-3(4H)-酮 在 三氯化铝 作用下， 生成 6-acetyl-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-3-one
  参考文献：
  名称：

  Techer,H. et al., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1970, vol. 270, p. 1601 - 1604

  摘要：

  DOI：

文献信息

• Facile Diversity-Oriented Synthesis and Antitubercular Evaluation of Novel Aryl and Heteroaryl Tethered Pyridines and Dihydro-6<i>H</i>-quinolin-5-ones Derived via Variants of the Bohlmann–Rahtz Reaction
  作者：Srinivas Kantevari、Santhosh Reddy Patpi、Dinesh Addla、Siddamal Reddy Putapatri、Balasubramanian Sridhar、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1021/co2000604

  日期：2011.7.11

  nes tethered with aryls and heteroaryls was achieved in very good yields through CeCl3·7H2O-NaI catalyst via variants of the Bohlmann–Rahtz reaction. β-Enaminones derived from various aryl and heteroaryl methyl ketones were regioselectively reacted with ethyl acetoacetate or 5,5-dimethylcyclohexane-1,3-dione or 4,4-dimethylcyclohexane-1,3-dione and ammonium acetate refluxing in 2-propanol. Applicability

  通过CeCl 3 ·7H 2可以很好的收率实现取代的吡啶和与芳基和杂芳基连接的二氢-6 H-喹啉-5-酮的多样性合成通过Bohlmann–Rahtz反应的变体生成O-NaI催化剂。使衍生自各种芳基和杂芳基甲基酮的β-烯酮与乙酰乙酸乙酯或5,5-二甲基环己烷-1,3-二酮或4,4-二甲基环己烷-1,3-二酮和乙酸铵在2-丙醇中回流进行区域选择性反应。无毒铈催化剂的适用性，与宽范围的芳基和杂芳基β-烯胺酮具有高反应活性，从而导致各种类似物，操作简便以及在相对较低的温度下较短的反应时间是已开发方案的突出特点。已评估了这些合成的取代吡啶和二氢-6 H-喹啉-5-酮类似物对结核分枝杆菌的体外抗分枝杆菌活性通过琼脂稀释法获得H37Rv（MTB）。在筛选出的48种化合物中，有6种化合物2-（5-氯噻吩-2-基）-7,7-二甲基-7,8-二氢-6 H-喹啉-5-一4 13,2 }，2-（ 5-溴噻吩-2-基-7
• Pd-catalyzed site selective C–H acetoxylation of aryl/heteroaryl/thiophenyl tethered dihydroquinolinones
  作者：Santhosh Reddy Patpi、Balasubramanian Sridhar、Prabhakar Rao Tadikamalla、Srinivas Kantevari

  DOI：10.1039/c3ra41312h

  日期：——

  Described herein is an efficient protocol for the site selective oxidative C–H activation/acetoxylation of a series of 2-aryl/heteroaryl/thiophenyl tethered dihydroquinolinones using palladium acetate as the catalyst and iodobenzene diacetate as an oxidant. All these transformations progressed well at less sterically encumbered and electronically favourable C–H bonds to give corresponding ortho-acetoxylated derivatives in good yields. Further, acetoxylation of thiophenyl embedded dihydroquinolinones resulted in single regioisomers, acetoxylated at the C-2 position on the thiophenyl moiety. However, when the C-2 position on the thiophene unit was blocked, the acetoxy group was exclusively installed at the C-4 position. Further, we noticed that acetoxylation of dihydroquinolin-5(6H)-one-oxime did not alter ligand preferentiality to give the ortho-acetoxylated product.

  本文描述了一种高效的选择性氧化C–H活化/乙酰氧基化协议，适用于一系列连接有2-芳基/杂芳基/噻吩基的二氢喹啉酮，使用醋酸钯作为催化剂，碘苯二乙酸作为氧化剂。所有这些反应在立体障碍较小且电子性质良好的C–H键上进行良好，生成相应的邻位乙酰氧基化衍生物，收率良好。此外，嵌入噻吩基的二氢喹啉酮的乙酰氧基化反应导致产生单一的区域异构体，乙酰氧基在噻吩基部分的C-2位上。然而，当噻吩单元的C-2位被阻塞时，乙酰氧基则会独占性地安装在C-4位上。此外，我们注意到，二氢喹啉-5(6H)-酮-肟的乙酰氧基化并未改变配体的优先性，仍然生成邻位乙酰氧基化产物。
• Carboxamide Compounds and Their Use
  申请人：Ben-Zeev Efrat

  公开号：US20100324035A1

  公开（公告）日：2010-12-23

  Chemokine receptor antagonists, in particular, compounds of Formula (I-A) that act as antagonists of the chemokine CCR2 receptor, including pharmaceutical compositions and uses thereof to treat or prevent diseases associated with monocyte accumulation, lymphocyte accumulation or leukocyte accumulation are described herein.

  化学因子受体拮抗剂，特别是化合物式(I-A)的拮抗剂，作为化学因子CCR2受体的拮抗剂，包括其药物组合物和用途，用于治疗或预防与单核细胞聚集、淋巴细胞聚集或白细胞聚集相关的疾病。
• [EN] DIHYDRONAPHTHYRIDINYL AND RELATED COMPOUNDS FOR USE IN TREATING OPHTHALMOLOGICAL DISORDERS<br/>[FR] DIHYDRONAPHTYRIDINYLE ET COMPOSÉS APPARENTÉS UTILISABLES DANS LE CADRE DU TRAITEMENT DE TROUBLES OPHTALMOLOGIQUES
  申请人：CYTOPATHFINDER INC

  公开号：WO2010129843A1

  公开（公告）日：2010-11-11

  The invention provides methods of using dihydronaphthyridinyl and related compounds to treat ophthalmological disorders, such as, wet age-related macular degeneration, diabetic retinopathy, and high myopia. Pharmaceutical compositions and methods of synthesizing the dihydronaphthyridinyl and related compounds are provided.

  这项发明提供了使用二氢萘啉基和相关化合物治疗眼科疾病的方法，如湿性年龄相关性黄斑变性、糖尿病视网膜病变和高度近视。还提供了制备二氢萘啉基和相关化合物的药物组合物和合成方法。
• Novel Carbapenem Compound
  申请人：Sunagawa Makoto

  公开号：US20070265242A1

  公开（公告）日：2007-11-15

  A carbapenem compound represented by a following formula [1], wherein R 1 is C 1 to C 3 alkyl or C 1 to C 3 alkyl substituted by hydroxy. R is hydrogen atom or a group which regenerates a carboxyl group by hydrolysis in a living body, A is a following formula [1a], wherein E is a 5 to 7 membered cyclic ring optionally containing 1 to 3 hetero atoms (excluding benzene ring) which forms a bicyclic ring in corporation with the benzene ring, Y is hydrogen atom, C 1 to C 4 alkyl, C 1 to C 4 alkoxy, trifluoromethoxy, halogen atom or cyano group, or its pharmaceutically acceptable salt.

  一种碳青霉烯化合物，其化学式为[1]，其中R1为C1到C3烷基或C1到C3烷基被羟基取代，R为氢原子或在活体内通过水解再生羧基团的基团，A为以下化学式[1a]，其中E是一个5到7个成员的环状环，可选地含有1到3个杂原子（不包括苯环），与苯环结合形成双环，Y为氢原子，C1到C4烷基，C1到C4烷氧基，三氟甲氧基，卤原子或氰基，或其药学上可接受的盐。