6-甲氧基-3-二氢色原酮 | 76322-25-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 6-甲氧基-3-二氢色原酮
• 中文别名: 6-甲氧基-3-苯并二氢吡喃酮
• 英文名称: 6-methoxy-3,4-dihydro-2H-1-benzopyran-3-one
• 英文别名: 6-methoxychroman-3-one；6-methoxy-2H-[1]-benzopyran-3-one；6-methoxy-3-chromanone；6-methoxy-4H-chromen-3-one
• CAS: 76322-25-3
• 化学式: C₁₀H₁₀O₃
• 分子量: 178.188
• InChiKey: KUNSCSSLJIBBFD-UHFFFAOYSA-N

物化性质

• 熔点：
  67-72 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  320.4±42.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-甲氧基-3-二氢色原酮 生成 ethyl 6-methoxy-3-chromanylideneacetate
  参考文献：
  名称：

  Bicyclic compound and platelet aggregation inhibitor containing the same

  摘要：

  该发明涉及一种新型化合物，其化学式表示为（1），基于纤维蛋白原拮抗作用具有出色的抑制血小板聚集作用。含有化合物（1）的血小板聚集抑制剂作为有效成分对预防和治疗血栓形成以及经皮透支式冠状动脉成形术或经皮透支式冠状动脉再通术后的再狭窄或再闭塞具有有效性。

  公开号：

  US05629321A1
• 作为产物：
  描述：

  6-甲氧基-2H-色烯-3-甲腈 在 盐酸 、 sodium hydroxide 、 叠氮磷酸二苯酯 、 三乙胺 作用下， 反应 9.5h， 生成 6-甲氧基-3-二氢色原酮
  参考文献：
  名称：

  6- and 8-Hydroxy-3,4-dihydro-3-(dipropylamino)-2H-1-benzopyrans. Dopamine agonists with autoreceptor selectivity

  摘要：

  The dopamine agonist profiles of 3,4-dihydro-3-(3-dipropylamino)-2H-1-benzopyran-6- and -8-ol (4 and 5, respectively) were examined. Both 4 and 5 exhibited greater relative affinity for receptors labeled with the dopamine agonist ligand [3H]propylnorapomorphine than for those labeled with the dopamine antagonist ligand [3H]haloperidol. Both compounds attenuated the stimulation of brain dopamine synthesis caused by gamma-butyrolactone (GBL) and decreased the firing rate of substantia nigra dopamine neurons in rats. This profile of activity, together with the ability of the dopamine antagonist haloperidol to reverse the inhibition of dopamine neuronal firing, indicate that both compounds are brain dopamine agonists.

  DOI：

  10.1021/jm00398a032

文献信息

• BICYCLIC HETEROCYCLIC DERIVATIVES AS BROMODOMAIN INHIBITORS
  申请人：ORION CORPORATION

  公开号：US20160368906A1

  公开（公告）日：2016-12-22

  The present disclosure provides bicyclic heterocyclic derivatives of formula (I), which may be therapeutically useful, more particularly as bromodomain inhibitors; (I), in which R 1 , R 2 , R 3 , R 4 , L 1 , L 2 , Cy 1 , Cy 2 , X, n, and dotted line have the same meaning given in the specification, and pharmaceutically acceptable salts or pharmaceutically acceptable stereoisomers thereof that are useful in the treatment and prevention of diseases or disorders, in particular their use in diseases or disorders associated as bromodomain inhibitors. The present disclosure also provides preparation of compounds and pharmaceutical formulations comprising at least one of bicyclic heterocyclic derivatives of formula (I), together with a pharmaceutically acceptable carrier, diluent, or excipient.

  本公开提供了公式（I）的双环杂环衍生物，可能在治疗上有用，更具体地作为溴结构域抑制剂；（I）中，R1、R2、R3、R4、L1、L2、Cy1、Cy2、X、n和虚线具有规范中给定的相同含义，以及其在治疗和预防疾病或疾病中有用，特别是在与溴结构域抑制剂相关的疾病或疾病中的使用。本公开还提供了制备化合物和包括至少一种公式（I）的双环杂环衍生物的药物配方，以及药学上可接受的载体、稀释剂或赋形剂。
• Photochemical behaviour of 3.4-epoxyprecocene-I and related epoxychromans
  作者：G. Ariamala、K.K. Balasubramanian

  DOI：10.1016/s0040-4020(01)89238-3

  日期：1989.1

  A systematic study of photochemical behaviour of 3,4-epoxyprecocene-I and related epoxychromans was undertaken. Upon irradiation in acetone or cyclohexane, 3,4-epoxyprecocene-I was found to undergo photoisomerisation to the corresponding 3-chromanone . In contrast, the photochemical behaviour of analogous 3,4-dihydro-3,4-epoxy-2H-1-benzopyrans 3 was found to be dependent upon the nature of solvent

  进行了系统的研究3,4-epoxyprecocene-I和相关的环氧chromans的光化学行为。在丙酮或环己烷中辐照后，发现3，4-环氧前十烯-1经历光异构化为相应的3-苯并二氢吡喃酮。相反，发现类似的3，4-二氢-3，4-环氧-2H-1-苯并吡喃3的光化学行为取决于溶剂的性质。在环己烯中辐射3导致光脱羰基化导致2,3-二氢苯并呋喃的形成，而在丙酮中辐射导致chramanones的形成。
• Rapid Access to Chroman-3-ones through Gold-Catalyzed Oxidation of Propargyl Aryl Ethers
  作者：Yanzhao Wang、Kegong Ji、Sylvester Lan、Liming Zhang

  DOI：10.1002/anie.201107561

  日期：2012.2.20

  two‐step: Chroman‐3‐ones are important intermediates for organic synthesis and medicinal chemistry. However, their syntheses require multiple steps and are not efficient. By using gold‐catalyzed alkyne oxidation, this versatile heterocycle can be prepared in only two steps from readily available phenols and with mostly high efficiencies (see scheme).

  两步法：Chroman-3-ones 是有机合成和药物化学的重要中间体。然而，它们的合成需要多个步骤并且效率不高。通过使用金催化的炔烃氧化，这种多功能杂环可以从容易获得的酚类中仅通过两步来制备，而且效率很高（参见方案）。
• Certain benzo-(pyrano and thiopyrano)-pyridines, useful as CNS agents
  申请人：Ciba-Geigy Corporation

  公开号：US04604397A1

  公开（公告）日：1986-08-05

  Disclosed are the compounds of formula I ##STR1## wherein X represents oxygen or sulfur; ring A is unsubstituted or substituted by one to three identical or different substituents selected from hydroxy, hydroxy-lower alkyl, etherified hydroxy, etherified hydroxy-lower alkyl, acyloxy, acyloxy-lower alkyl, halogen, lower alkyl, trifluoromethyl, amino, mono- and di-lower alkylamino and acylamino; or ring A is substituted by one lower alkylenedioxy; R represents hydrogen, lower alkyl or aryl-lower alkyl; R.sub.1 represents hydrogen, lower alkyl, lower alkylthio-lower alkyl, amino, acylamino, (amino, mono- or di-lower alkylamino)-lower alkyl, carboxy, lower alkoxycarbonyl, carbamoyl or mono- or di-lower alkylcarbamoyl; R.sub.2 to R.sub.5 represent hydrogen or lower alkyl; the dehydro derivatives thereof with a double bond at the 1,2-position, or at the 1,10b-position in which case R.sub.5 is absent; or a pharmaceutically acceptable salt thereof; methods for their synthesis; pharmaceutical compositions thereof; and use thereof as psychactive agents for the treatment of central nervous system disorders.

  公开了公式I的化合物，其中X代表氧或硫；环A未取代或被一个至三个相同或不同的取代基取代，所述取代基选自羟基、羟基较低烷基、醚化的羟基、醚化的羟基较低烷基、酰氧基、酰氧基较低烷基、卤素、较低烷基、三氟甲基、氨基、单烷基氨基和二烷基氨基以及酰氨基；或环A被一个较低烷基二氧基取代；R代表氢、较低烷基或芳基较低烷基；R.sub.1代表氢、较低烷基、较低烷硫基、氨基、酰氨基、（氨基、单烷基氨基或二烷基氨基）较低烷基、羧基、较低烷氧羰基、氨基甲酰基或单烷基或二烷基氨基甲酰基；R.sub.2到R.sub.5代表氢或较低烷基；具有1,2-位置处的双键的脱氢衍生物，或者在1,10b-位置处的双键，此时R.sub.5不存在；或其药学上可接受的盐；其合成方法；其药物组成物；以及作为治疗中枢神经系统疾病的精神活性剂的用途。
• 3-amino-dihydro-(1)-benzopyrans
  申请人：Ciba-Geigy Corporation

  公开号：US04992465A1

  公开（公告）日：1991-02-12

  ##STR1## wherein Z represents O or S; R represents hydrogen or lower alkyl; R.sub.1 represents hydrogen, lower alkyl or aryl-lower alkyl; R.sub.2 represents hydrogen, lower alkyl or aryl-lower alkyl; or R.sub.1 and R.sub.2 together represent alkylene of 4 to 6 carbon atoms; R.sub.3 represents hydrogen, hydroxy, lower alkoxy, aryl-lower alkoxy, acyloxy or aryloxy in compounds wherein Z represents S; or R.sub.3 represents hydroxy, lower alkoxy, aryl-lower alkoxy, acyloxy or aryloxy, and is attached only at the 5- or 8- position in compounds wherein Z represents O; R.sub.4 and R.sub.5 represent independently hydrogen, lower alkyl or halogen; and pharmaceutically acceptable salts thereof; and mono or di- S-oxides of compounds of formula I wherein Z represents S and pharmaceutically acceptable salts thereof, pharmaceutical compositions thereof; and use thereof as central nervous system active agents for the treatment of central nervous system disorders.

  其中Z代表O或S；R代表氢或低碳基；R.sub.1代表氢，低碳基或芳基-低碳基；R.sub.2代表氢，低碳基或芳基-低碳基；或R.sub.1和R.sub.2一起代表4至6个碳原子的烷基；R.sub.3代表氢，羟基，低烷氧基，芳基-低烷氧基，酰氧基或芳氧基，在Z代表S的化合物中；或R.sub.3代表羟基，低烷氧基，芳基-低烷氧基，酰氧基或芳氧基，并且仅在Z代表O的化合物中附着于5-或8-位置；R.sub.4和R.sub.5独立地代表氢，低碳基或卤素；以及其药学上可接受的盐；以及式I化合物的单或双S-氧化物，其中Z代表S及其药学上可接受的盐，其制药组合物；以及作为中枢神经系统活性剂治疗中枢神经系统疾病的用途。