3,4-Dihydro-4-methyl-2H-1,4-benzoxazin-2-ylmethanol | 84831-43-6

• 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: 3,4-Dihydro-4-methyl-2H-1,4-benzoxazin-2-ylmethanol
• 英文别名: (4-methyl-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methanol；N-methyl-2-hydroxymethyl-benzomorpholine；(4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)methanol；4-methyl-3,4-dihydro-2H-1,4-benzoxazin-2-methanol；4-methyl-3,4-dihydro-1,4-benzoxazin-2-methanol；(4-methyl-2,3-dihydro-1,4-benzoxazin-2-yl)methanol
• CAS: 84831-43-6
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: JXHXGRFRNVQDJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-Dihydro-4-methyl-2H-1,4-benzoxazin-2-ylmethanol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 4-methyl-3,4-dihydro-2H-1,4-benzoxazine-2-carbaldehyde
  参考文献：
  名称：

  快速氧化制备4 H -1,4-Benzoxazine-2-carbaldehydes的简单方法

  摘要：

  饱和（1,4-苯并恶嗪-2-基）-甲醇2的剧烈氧化提供4 H -1,4-苯并恶嗪-2-甲醛3，它们具有α，β烯键。检查了这些化合物的反应性。

  DOI：

  10.1002/jhet.5570330133
• 作为产物：
  描述：

  4-methyl-4H-1,4-benzoxazine-2-carbaldehyde 在 Palladium-Kohle 氢气 作用下， 以 乙醇 为溶剂， 生成 3,4-Dihydro-4-methyl-2H-1,4-benzoxazin-2-ylmethanol
  参考文献：
  名称：

  Bartsch, Herbert; Schwarz, Otto, Journal of Heterocyclic Chemistry, 1982, vol. 19, p. 1189 - 1193

  摘要：

  DOI：

文献信息

• Enantioselective Desymmetrization of 3-Substituted Oxetanes: An Efficient Access to Chiral 3,4-Dihydro-2<i>H</i>-1,4-benzoxazines
  作者：Viraj A. Bhosale、Martin Nigríni、Martin Dračínský、Ivana Císařová、Jan Veselý

  DOI：10.1021/acs.orglett.1c03419

  日期：2021.12.17

  Herein, we describe a versatile transition metal/oxidant free synthesis of the chiral 2H-1,4-benzoxazines through chiral phosphoric acid (CPA) catalyzed enantioselective desymmetrization of prochiral oxetanes (30 examples) in up to 99% yield and 99% enantioselectivity under mild reaction conditions. The reported strategy not only complements the conventional 2H-1,4-benzoxazine synthetic strategies

  在此，我们描述了一种通用的无过渡金属/无氧化剂合成手性 2 H -1,4-苯并恶嗪，通过手性磷酸 (CPA) 催化前手性氧杂环丁烷的对映选择性去对称化（30 个实例），收率高达 99%，对映选择性高达 99%在温和的反应条件下。报告的策略不仅补充了传统的 2 H -1,4-苯并恶嗪合成策略，而且还提供了获得治疗候选物的关键中间体，即前列腺素 D2 受体拮抗剂和 M1 正变构调节剂 (PAM) 化合物 VU0486846。
• Discovery of a new class of potent, selective, and orally active prostaglandin D2 receptor antagonists
  作者：Kazuhiko Torisu、Kaoru Kobayashi、Maki Iwahashi、Yoshihiko Nakai、Takahiro Onoda、Toshihiko Nagase、Isamu Sugimoto、Yutaka Okada、Ryoji Matsumoto、Fumio Nanbu、Shuichi Ohuchida、Hisao Nakai、Masaaki Toda

  DOI：10.1016/j.bmc.2004.07.048

  日期：2004.10

  acetic acid analogs is presented since these compounds represent a new class of potent, selective, and orally active prostaglandin D2 (PGD2) receptor antagonists. Most of these compounds exhibit strong PGD2 receptor binding and PGD2 receptor antagonism in cAMP formation assays. When given orally, these new antagonists dramatically suppress allergic inflammatory responses, such as the PGD2-induced or

  提出了发现一系列N-（对烷氧基）苯甲酰基-2-甲基吲哚-4-乙酸类似物的过程，因为这些化合物代表了一类新的强效，选择性和口服活性前列腺素D2（PGD2）受体拮抗剂。这些化合物大多数在cAMP形成分析中表现出较强的PGD2受体结合和PGD2受体拮抗作用。口服时，这些新的拮抗剂可显着抑制过敏性炎症反应，例如PGD2诱导或OVA诱导的血管通透性增加。还讨论了结构活动关系（SAR）数据。
• 2,6-Difluorobenzamide Inhibitors of Bacterial Cell Division Protein FtsZ: Design, Synthesis, and Structure-Activity Relationships
  作者：Valentina Straniero、Carlo Zanotto、Letizia Straniero、Andrea Casiraghi、Stefano Duga、Antonia Radaelli、Carlo De Giuli Morghen、Ermanno Valoti

  DOI：10.1002/cmdc.201700201

  日期：2017.8.22

  filamentous temperature-sensitive Z (FtsZ) has emerged as a possible target, thanks to its ubiquitous expression and its homology to eukaryotic β-tubulin. In the latest years, several compounds were shown to interact with this prokaryotic protein and selectively inhibit bacterial cell division. Recently, our research group developed interesting derivatives displaying good antibacterial activities against

  各种耐药微生物不断涌现，限制了常见细菌感染的治疗选择。原本有效的抗菌剂由于对这些抗药性细菌的活性弱或无效而不再有用。此外，最近批准的抗生素均未影响创新目标，因此需要具有创新抗菌作用机制的新型药物。由于其普遍存在的表达及其与真核β-微管蛋白的同源性，必需的细胞分裂蛋白丝状温度敏感Z（FtsZ）已成为可能的靶标。在最近几年中，几种化合物显示出与该原核蛋白相互作用并选择性抑制细菌细胞分裂。最近，我们的研究小组开发了有趣的衍生物，它们对耐甲氧西林的金黄色葡萄球菌，耐万古霉素的粪肠球菌和结核分枝杆菌具有良好的抗菌活性。本研究的目的是总结不同取代的杂环的结构-活性关系，这些杂环通过亚甲基氧桥连接到2,6-二氟苯甲酰胺，并验证FtsZ作为此类抗菌剂的真正目标。
• Bicyclic compounds and their use in medicine, process for their preparation and pharmaceutical compositions containing them
  申请人：Reddy-Cheminor, Inc.

  公开号：US06265401B1

  公开（公告）日：2001-07-24

  Compounds of formula (I) its tautomeric forms, its stereoisomers, its polymorphs, its pharmaceutically acceptable salts or its pharmaceutically acceptable solvates can be used to prevent or treat diabetes caused by insulin resistance or impaired glucose tolerance or complications of diabetes caused by insulin resistance or impaired glucose tolerance. The compounds can also be used to reduce cholesterol, body weight, blood glucose, triglycerides and free fatty acids in the blood.

  式(I)的化合物、其互变异构体、立体异构体、多晶型、药学上可接受的盐或药学上可接受的溶剂，可用于预防或治疗由胰岛素抵抗或糖耐量受损引起的糖尿病或由胰岛素抵抗或糖耐量受损引起的糖尿病并发症。这些化合物还可用于降低血液中的胆固醇、体重、血糖、甘油三酯和游离脂肪酸水平。
• Substituted bicyclic heterocycles, process for their preparation and their use as antiobesity and hypocholesterolemic agents
  申请人：Dr. Reddy's Laboraties Limited

  公开号：US07348426B1

  公开（公告）日：2008-03-25

  The present invention relates to novel antiobesity and hypocholesterolemic compounds, their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them. More particularly, the present invention relates to novel β-aryl-α-oxysubstituted alkylcarboxylic acids of general formula (I), their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them

  本发明涉及新型抗肥胖和降低胆固醇的化合物、它们的衍生物、类似物、互变异构体、立体异构体、多晶形态、药学上可接受的盐、药学上可接受的溶剂和药学上可接受的含有它们的组合物。更具体地，本发明涉及一般式(I)的新型β-芳基-α-氧代取代烷基羧酸、它们的衍生物、类似物、互变异构体、立体异构体、多晶形态、药学上可接受的盐、药学上可接受的溶剂和药学上可接受的含有它们的组合物。