4-allylcoumarine | 160749-21-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-allylcoumarine
• 英文别名: 4-Allylcoumarin；4-prop-2-enylchromen-2-one
• CAS: 160749-21-3
• 化学式: C₁₂H₁₀O₂
• 分子量: 186.21
• InChiKey: LVMYWLOONIGNAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2-oxo-2H-chromen-4-yl)zinc bromide 、 3-溴丙烯 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以83%的产率得到4-allylcoumarine
  参考文献：
  名称：

  一种新型的有机锌试剂4-香豆素基溴化锌；取代香豆素衍生物的制备及其在合成中的应用

  摘要：

  通过将活性锌直接氧化加成到4-溴香豆素中，制得了一种新型的有机锌试剂溴化4-香豆素锌。所得的有机溴化锌与钯的各种芳基卤化物和酰氯进行交叉催化的交叉偶联反应，在温和的条件下以良好的收率得到相应的偶联产物。

  DOI：

  10.1016/j.tetlet.2011.03.151

文献信息

• Compound
  申请人：Reed John Michael

  公开号：US20050154050A1

  公开（公告）日：2005-07-14

  A compound is described. In particular, a non-steroidal sulphamate compound is described. The compound is suitable for use as an inhibitor of oestrone sulphatase. The compound is of general Formula (A), wherein R 1 -R 6 are independently selected from H, halo, hydroxy, sulphamate, alkyl and substituted variants or salts thereof; but wherein at least one of R 1 -R 6 is a sulphamate group; and wherein X is any one of S, NH, a substituted N, CH 2 , or a substituted C.

  描述了一种化合物。具体地，描述了一种非甾体磺酸酯化合物。该化合物适用于用作雌二醇磺酸酶的抑制剂。该化合物具有通用的A式，其中R1-R6独立选择自H、卤素、羟基、磺酸酯、烷基和其取代物或盐；但是其中至少一个R1-R6是磺酸酯基；且X是S、NH、取代N、CH2或取代C中的任意一种。
• Coumarin intermediates
  申请人：BEECHAM GROUP PLC

  公开号：EP0050396A1

  公开（公告）日：1982-04-28

  Compounds of the formula (II): or a salt thereof, wherein R is hydrogen or an alkyl group containing up to 6 carbon atoms; X is a covalent bond or oxygen; Y is -(CH2)n- where n is 0 or an integer from 1 to 5 wherein one carbon atom not bound to the nitrogen atom may be optionally substituted with a hydroxy group; and Z is hydrogen or halogen are useful intermediates in the preparation of pharmacologically active compounds described in European Patent Application No 79302141.

  式 (II) 的化合物：或其盐，其中 R 是氢或最多含有 6 个碳原子的烷基；X 是共价键或氧；Y 是-(CH2)n-，其中 n 是 0 或 1 至 5 的整数，其中未与氮原子结合的一个碳原子可任选被羟基取代；Z 是氢或卤素，是制备欧洲专利申请第 79302141 号所述药理活性化合物的有用中间体。
• Method for the preparation of (+/-)-calanolide A
  申请人：MEDICHEM RESEARCH, INC.

  公开号：EP1054007A2

  公开（公告）日：2000-11-22

  A method of preparing (±)-calanolide A, 1, a potent HIV reverse transcriptase inhibitor, from chromene 4 is provided. Useful intermediates for preparing (±)-calanolide A and its derivatives are also provided. According to the disclosed method, chromene 4 intermediate was reacted with acetaldehyde diethyl acetal or paraldehyde in the presence of an acid catalyst with heating, or a two-step reaction including an aldol reaction with acetaldehyde and cyclization either under acidic conditions or neutral Mitsunobu conditions, to produce chromanone 7. Reduction of chromanone 7 with sodium borohydride, in the presence of cerium trichloride, produced (±)-calanolide A. A method for resolving (±)-calanolide A into its optically active forms by a chiral HPLC system or by enzymatic acylation and hydrolysis is also disclosed. Finally, a method for treating or preventing viral infections using (±)-calanolide or (-)-calanolide is provided.

  本研究提供了一种由色烯 4 制备 (±)-calanolide A, 1 的方法，(±)-calanolide A, 1 是一种有效的 HIV 逆转录酶抑制剂。还提供了制备 (±)-calanolide A 及其衍生物的有用中间体。根据所公开的方法，在酸性催化剂存在下，加热铬烯 4 中间体与乙醛二乙缩醛或副醛反应，或在酸性条件下或中性三忍条件下进行两步反应，包括与乙醛的醛醇反应和环化反应，生成色满酮 7。在三氯化铈存在下，用硼氢化钠还原色满酮 7，生成(±)-丙醇内酯 A。此外，还公开了一种通过手性 HPLC 系统或酶酰化和水解将 (±)-calanolide A 分解为其光学活性形式的方法。最后，还提供了一种使用 (±)-calanolide 或 (-)-calanolide 治疗或预防病毒感染的方法。
• Method for the preparation of chromanone
  申请人：Sarawak Medichem Pharmaceuticals Inc.

  公开号：EP1308448A1

  公开（公告）日：2003-05-07

  The application describes the conversion of chromene 4 to chromanome 7.

  该申请描述了将色度 4 转换为色度 7 的过程。
• PLANT EXTRACT OBTAINED FROM KIELMEYERA AUREOVINOSA WHICH HAS ANTIBIOTIC ACTIVITY, ISOLATED CHEMICAL COMPOUND, COMPOSITIONS COMPRISING SAME, USES THEREOF AND METHODS FOR PREVENTING AND TREATING BACTERIAL INFECTIONS
  申请人：Extracta Moléculas Naturais S/A

  公开号：EP2735311A1

  公开（公告）日：2014-05-28

  The present invention refers primarily to a plant extract obtained from Kielmeyera aureovinosa which has accentuated antibiotic activity. In a second modality, the invention describes a new chemical compound isolated from the same, as well as variations thereof. In other terms, the present invention provides compositions comprising a phytotherapic obtained from said plant extract, as well as veterinary pharmaceutical compositions comprising isolated compounds and variations of the same. Additionally, the present invention provides uses of the plant extract, chemical compounds and compositions comprising the same for the preparation of medicines for the prevention or treatment of bacterial infections, as well as methods of prevention or treatment of the same.

  本发明主要涉及一种从 Kielmeyera aureovinosa 中提取的植物提取物，它具有更强的抗生素活性。在第二种模式中，本发明描述了从该提取物中分离出来的一种新化合物及其变体。换言之，本发明提供了包含从上述植物提取物中获得的植物治疗剂的组合物，以及包含分离化合物及其变体的兽药组合物。 此外，本发明还提供了植物提取物、化合物和包含上述物质的组合物在制备预防或治疗细菌感染的药物中的用途，以及预防或治疗细菌感染的方法。