2-methylidene-3,4-dihydro-2H-1,4-benzoxazine | 343270-95-1

• 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: 2-methylidene-3,4-dihydro-2H-1,4-benzoxazine
• 英文别名: 2-Methylidene-3,4-dihydro-1,4-benzoxazine
• CAS: 343270-95-1
• 化学式: C₉H₉NO
• mdl: MFCD19227855
• 分子量: 147.177
• InChiKey: XTOKFSYADQIFED-UHFFFAOYSA-N

物化性质

• 沸点：
  258.8±30.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(丙-2-炔-1-基氨基)苯酚 在 三苯基膦氯金 、 silver trifluoromethanesulfonate 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 以45%的产率得到2-methylidene-3,4-dihydro-2H-1,4-benzoxazine
  参考文献：
  名称：

  An Alternative Synthesis of 2-Alkylidene-3,4-dihydro-2H-1,4-benzoxazines by Intramolecular Gold-Catalyzed Hydroalkoxylation of 2-(Prop-2-yn-1-ylamino)phenols

  摘要：

  以 2-炔基取代的苯酚为起点，开发出了一种合成 2-亚烷基-3,4-二氢-2H-1,4-苯并噁嗪的高效金催化步骤。这是一种以苯酚为基团的炔烃的分子内氢烷氧基化反应，是已报道的过渡金属催化程序的重要替代品。

  DOI：

  10.1055/s-0030-1258346

文献信息

• Pparalpha/Gamma Agonists and Processes of Preparing
  申请人：Garrett Christine E.

  公开号：US20080221336A1

  公开（公告）日：2008-09-11

  This invention provides a method for preparing compounds having the structure [Formula (I)] wherein L is [Formula (A)] or [Formula (B)] in which R 1 is hydrogen or optionally substituted alkyl, n is zero or 1 and m is 1; wherein R is H, halogen, optionally substituted C 1-6 alkyl or C 1-6 alkoxy; wherein Z is a bond, O or S; wherein p is an integer from 1 to 5; wherein Q is a bond provided that Z is not a bond when p is 1; or Q is O, S or —C(O)NR 6 — in which R 6 is hydrogen, optionally substituted alkyl or cycloalkyl; or Q is —NR 6 —, —NR 5 C(O)NH— or —NR 5 C(O)O— in which R 5 is hydrogen, alkyl or aralkyl provided that p is not 1; wherein W is cycloalkyl, aryl or heterocyclyl; or W and R 6 form a 9- to 10-membered bicyclic ring, which may be optionally substituted or may contain oxygen, nitrogen or sulfur.

  该发明提供了一种制备具有结构[Formula (I)]的化合物的方法，其中L为[Formula (A)]或[Formula (B)]，其中R1为氢或可选择取代的烷基，n为零或1，m为1；其中R为H，卤素，可选择取代的C1-6烷基或C1-6烷氧基；其中Z为键，O或S；其中p为1到5的整数；其中Q为一种键，前提是当p为1时Z不是键；或Q为O，S或—C(O)NR6—，其中R6为氢，可选择取代的烷基或环烷基；或Q为—NR6—，—NR5C(O)NH—或—NR5C(O)O—，其中R5为氢，烷基或芳基，前提是p不为1；其中W为环烷基，芳基或杂环烷基；或W和R6形成一个9到10元的双环环，可以选择性取代或含有氧、氮或硫。
• HETEROCYCLIC COMPOUNDS AND METHODS OF USE
  申请人：Bach Thomas Andrew

  公开号：US20070135502A1

  公开（公告）日：2007-06-14

  Compounds of the formula provide pharmacological agents which are potent agonists of Peroxisome Proliferator-Activated Receptors (PPARs). Accordingly, the compounds of the instant invention are useful for the treatment of conditions mediated by the PPAR receptor activity in mammals. Such conditions include dyslipidemia, hyperlipidemia, hypercholesteremia, atherosclerosis, hypertriglyceridemia, heart failure, myocardial infarction, vascular diseases, cardiovascular diseases, hypertension, obesity, inflammation, arthritis, cancer, Alzheimer's disease, skin disorders, respiratory diseases, ophthalmic disorders, inflammatory bowel diseases, ulcerative colitis and Crohn's disease. The compounds of the present invention are particularly useful in mammals as hypoglycemic agents for the treatment and prevention of conditions in which impaired glucose tolerance, hyperglycemia and insulin resistance are implicated, such as type-1 and type-2 diabetes, and Syndrome X. Preferred are the compounds of the invention which are dual agonists of PPARα and PPARγ receptors.

  该公式化合物提供了对过氧化物酶体增殖物激活受体（PPARs）具有强效激动剂作用的药理制剂。因此，本发明的化合物对于治疗哺乳动物PPAR受体活性介导的疾病是有用的。这些疾病包括：血脂异常、高血脂、高胆固醇血症、动脉粥样硬化、高三酰甘油血症、心力衰竭、心肌梗塞、血管疾病、心血管疾病、高血压、肥胖、炎症、关节炎、癌症、阿尔茨海默病、皮肤疾病、呼吸道疾病、眼科疾病、炎症性肠病、溃疡性结肠炎和克罗恩病。本发明的化合物在哺乳动物中作为降糖剂特别有用，用于治疗和预防出现受损的葡萄糖耐受性、高血糖和胰岛素抵抗的疾病，例如1型和2型糖尿病和X综合症。本发明的化合物中，对于同时激活PPARα和PPARγ受体的双重激动剂，更为优选。
• Organic compounds
  申请人：Damon Edson Robert

  公开号：US20070004704A1

  公开（公告）日：2007-01-04

  Compounds of the formula provide pharmacological agents which bind to Peroxisome Proliferator-Activated Receptors (PPARs). Accordingly, the compounds of the present invention are useful for the treatment of conditions mediated by the PPAR receptor activity in mammals. Such conditions include dyslipidemia, hyperlipidemia, hypercholesteremia, atherosclerosis, hypertriglyceridemia, heart failure, myocardial infarction, vascular diseases, cardiovascular diseases, hypertension, obesity, inflammation, arthritis, cancer, Alzheimer's disease, skin disorders, respiratory diseases, ophthalmic disorders, inflammatory bowel diseases (IBDs), ulcerative colitis and Crohn's disease. The compounds of the present invention are particularly useful in mammals as hypoglycemic agents for the treatment and prevention of conditions in which impaired glucose tolerance, hyperglycemia and insulin resistance are implicated, such as type-1 and type-2 diabetes, and Syndrome X.

  本发明的化合物具有以下公式，可提供与过氧化物酶体增殖物激活受体（PPARs）结合的药理剂。因此，本发明的化合物对于治疗哺乳动物中由PPAR受体活性介导的疾病是有用的。这些疾病包括失调脂质代谢、高脂血症、高胆固醇血症、动脉粥样硬化、高甘油三酯血症、心力衰竭、心肌梗死、血管疾病、心血管疾病、高血压、肥胖症、炎症、关节炎、癌症、阿尔茨海默病、皮肤疾病、呼吸系统疾病、眼部疾病、炎症性肠病（IBD）、溃疡性结肠炎和克罗恩病。本发明的化合物在哺乳动物中作为降糖药物特别有用，用于治疗和预防因受损葡萄糖耐受性、高血糖和胰岛素抵抗而引起的疾病，例如1型和2型糖尿病以及X综合症。
• Benzenesulfonylamino compounds and pharmaceutical compositions containing these compounds
  申请人：Vedananda Ralalage Thalaththani

  公开号：US20070043020A1

  公开（公告）日：2007-02-22

  Compounds of the formula provide pharmacological agents which bind to Peroxisome Proliferator-Activated Receptors (PPARs). Accordingly, the compounds of the instant invention are useful for the treatment of conditions mediated by the PPAR receptor activity in mammals. Such conditions include dyslipidemia, hyperlipidemia, hypercholesteremia, atherosclerosis, hypertriglyceridemia, heart failure, myocardial infarction, vascular diseases, cardiovascular diseases, hypertension, obesity, inflammation, arthritis, cancer, Alzheimer's disease, skin disorders, respiratory diseases, ophthalmic disorders, inflammatory bowel diseases (IBDs), ulcerative colitis and Crohn's disease, and conditions in which impaired glucose tolerance, hyperglycemia and insulin resistance are implicated, such as type-1 and type-2 diabetes, and Syndrome X.

  式的化合物提供了结合到过氧化物酶体增殖物激活受体（PPARs）的药理剂。因此，本发明的化合物对于治疗哺乳动物中PPAR受体活性介导的疾病是有用的。这些疾病包括失调脂质代谢，高脂血症，高胆固醇血症，动脉粥样硬化，高三酰甘油血症，心力衰竭，心肌梗死，血管疾病，心血管疾病，高血压，肥胖症，炎症，关节炎，癌症，阿尔茨海默病，皮肤疾病，呼吸系统疾病，眼科疾病，炎症性肠病（IBDs），溃疡性结肠炎和克罗恩病，以及涉及受损葡萄糖耐受性，高血糖和胰岛素抵抗的病症，例如1型和2型糖尿病和X综合症。
• Organic Compounds
  申请人：Damon Robert Edson

  公开号：US20100152255A1

  公开（公告）日：2010-06-17

  Compounds of the formula provide pharmacological agents which bind to Peroxisome Proliferator-Activated Receptors (PPARs). Accordingly, the compounds of the present invention are useful for the treatment of conditions mediated by the PPAR receptor activity in mammals. Such conditions include dyslipidemia, hyperlipidemia, hypercholesteremia, atherosclerosis, hypertriglyceridemia, heart failure, myocardial infarction, vascular diseases, cardiovascular diseases, hypertension, obesity, inflammation, arthritis, cancer, Alzheimer's disease, skin disorders, respiratory diseases, ophthalmic disorders, inflammatory bowel diseases (IBDs), ulcerative colitis and Crohn's disease. The compounds of the present invention are particularly useful in mammals as hypoglycemic agents for the treatment and prevention of conditions in which impaired glucose tolerance, hyperglycemia and insulin resistance are implicated, such as type-1 and type-2 diabetes, and Syndrome X.

  公式化合物提供了与过氧化物酶体增殖物激活受体（PPARs）结合的药理剂。因此，本发明的化合物对于治疗哺乳动物中PPAR受体活性介导的疾病是有用的。这些疾病包括失调脂质代谢症、高脂血症、高胆固醇血症、动脉硬化、高三酰甘油血症、心力衰竭、心肌梗死、血管疾病、心血管疾病、高血压、肥胖症、炎症、关节炎、癌症、阿尔茨海默病、皮肤疾病、呼吸系统疾病、眼科疾病、炎症性肠病（IBDs）、溃疡性结肠炎和克罗恩病。本发明的化合物在哺乳动物中作为降糖剂特别有用，用于治疗和预防因糖耐量受损、高血糖和胰岛素抵抗而引起的疾病，例如1型和2型糖尿病和X综合症。