6-溴-3-丁酰-2H-苯并吡喃-2-酮 | 2199-83-9

• 物质功能分类: 医药中间体 - 吡喃类化合物
• 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
• 中文名称: 6-溴-3-丁酰-2H-苯并吡喃-2-酮
• 中文别名: 6-溴-3-丁酰基香豆素
• 英文名称: 6-bromo-3-butyryl-coumarin
• 英文别名: 6-Brom-3-butyryl-cumarin；8-Brom-coumaryl-3-propylketon；6-bromo-3-butyryl-2H-chromen-2-one；6-bromo-3-butanoylchromen-2-one
• CAS: 2199-83-9
• 化学式: C₁₃H₁₁BrO₃
• 分子量: 295.133
• InChiKey: RDBKKAPCFCJFND-UHFFFAOYSA-N

物化性质

• 熔点：
  163-165°C
• 沸点：
  452.5±45.0 °C(Predicted)
• 密度：
  1.509±0.06 g/cm3(Predicted)
• 稳定性/保质期：

  避免氧化物接触，危险分解产物为一氧化碳、二氧化碳和溴化氢。

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  6-溴-3-丁酰-2H-苯并吡喃-2-酮 在 三苯基膦氢溴酸盐 、 二甲基亚砜 作用下， 反应 24.0h， 以64%的产率得到6-bromo-3-(2-hydroxybutanoyl)-2H-chromen-2-one
  参考文献：
  名称：

  PPh₃·HBr–DMSO: A Reagent System for Diverse Chemoselective Transformations

  摘要：

  The broad applicability of the hitherto unexplored reagent combination PPh3 center dot HBr-DMSO is exemplified with multiple highly diverse one-step transformations to synthetically useful building blocks, such as flavones, 4H-thiochromen-4-ones, alpha-hydroxy ketones, 1,4-naphthoquinones (including vitamin K-3), 2-bromo-3-substituted-1H-1-indenones, 2-rnethylthio-1H-1-indenones, 3-butyne-1,2-dione, and 4-pentene-2,3-diones. The simple and mild reaction conditions make the reagent superior in terms of yield and substrate scope in comparison with the existing alternatives.

  DOI：

  10.1021/acs.joc.5b00846
• 作为产物：
  描述：

  丁酰乙酸乙酯 、 5-溴水杨醛 在 哌啶 作用下， 生成 6-溴-3-丁酰-2H-苯并吡喃-2-酮
  参考文献：
  名称：

  Buu-Hoi et al., Bulletin de la Societe Chimique de France, 1957, p. 561

  摘要：

  DOI：

文献信息

• Synthesis of 5‐oxo‐5 <i>H</i> ‐chromeno[3,4‐ <i>c</i> ]pyridine‐1‐carbonitriles and features of their NMR spectra
  作者：Mohanad Shkoor、Haw‐Lih Su、Suzan Ahmed、Sarah Hegazy

  DOI：10.1002/jhet.3826

  日期：2020.2

  leading to 5‐oxo‐5H‐chromeno[3,4‐c]pyridine‐1‐carbonitriles were investigated. Reactions of 3‐aminocrotonirile with substituted salicylaldehydes provided 5‐oxo‐5H‐chromeno[3,4‐c]pyridine‐1‐carbonitriles with the same substituent on positions 2 and 4 of the system. The reaction of 3‐aminocrotonirile with variety of substituted 3‐acetylcoumarins lead to 5‐oxo‐5H‐chromeno[3,4‐c]pyridine‐1‐carbonitriles

  研究了导致5-氧代-5 H - chromeno [3,4- c ]吡啶-1-腈的两种不同方法。3-氨基巴豆腈与取代的水杨醛的反应提供了在系统2和4位上具有相同取代基的5-氧代-5 H - chromeno [3,4- c ]吡啶-1-腈。3-氨基巴豆腈与多种取代的3-乙酰香豆素的反应导致在位置2和4上具有不同取代基的5-氧代-5 H-色酚[3,4- c ]吡啶-1-腈经分光镜方法证实。在具有固定几何结构的结构中腈部分的存在导致芳族质子在10位置的高度低场移位。1 H NMR谱。取代基的电子因子引起该低场偏移的变化。
• Improved and Efficient Synthesis of Chromeno[4,3-<i>d</i>]pyrazolo [3,4-<i>b</i>]pyridin-6(3<i>H</i>)-ones and Their Fluorescence Properties
  作者：Xue-Cheng Liu、Wei Lin、Hui-Yan Wang、Zhi-Bin Huang、Da-Qing Shi

  DOI：10.1002/jhet.2104

  日期：2014.7

  A series of chromeno[4,3‐d]pyrazolo[3,4‐b]pyridin‐6(3H)‐one derivatives was easily and efficiently synthesized by the reaction of 2H‐chromen‐2‐ones with pyrazol‐5‐amines catalyzed by CuCl2⋅2H2O in ethanol. This protocol has the advantages of mild reaction conditions, easy work‐up, and high yields. These compounds were showed to have high fluorescence quantum yields, which mentioned their value as luminescence

  通过2 H -chromen-2-one与吡唑-5的反应可轻松高效地合成一系列chromeno [4,3- d ] pyrazolo [3,4- b ] pyridin-6（3 H）-one衍生物-胺通过催化的CuCl 2 ⋅2H 2 Ó乙醇。该方案的优点是反应条件温和，易于后处理和高收率。这些化合物显示出高的荧光量子产率，提到了它们作为发光或荧光探针的价值。
• An Efficient Synthesis of Chromeno[4,3-<i>d</i>]isoxazolo[5,4-<i>b</i>]pyridin-6-one Derivatives
  作者：Pei-Pei Jin、Xue-Cheng Liu、De-Qi Liu、Zhi-Bin Huang、Da-Qing Shi

  DOI：10.1002/jhet.2255

  日期：2015.11

  A series of chromeno[4,3‐d]isoxazolo[5,4‐b]pyridin‐6‐one derivatives were easily and efficiently synthesized by the reaction of 3‐acyl‐2H‐chromen‐2‐ones with isoxazol‐5‐amine in acetic acid. Some synthesized compounds were evaluated for their antiproliferative properties in vitro against cancer cells, and these compounds were found to have some activities.

  通过3酰基2 H铬2-2-酮与异恶唑5的反应可以轻松，高效地合成一系列chromeno [4,3- d ]异恶唑并[5,4 ‐ b ]吡啶-6-酮衍生物‐乙酸中的胺。评价了一些合成的化合物在体外对癌细胞的抗增殖性能，发现这些化合物具有一定的活性。
• USE OF COUMARIN DERIVATIVES IN ANTIFUNGAL THERAPY
  申请人：Novabiotics Limited

  公开号：EP2049511A1

  公开（公告）日：2009-04-22
• Polypeptides and Their Use
  申请人：O'NEIL Deborah

  公开号：US20140155321A1

  公开（公告）日：2014-06-05

  The present invention relates to a polypeptide or a product comprising said polypeptide for use in the treatment and/or prevention of a fungal infection caused by Malassezia spp. and/or a Malassezia spp associated condition wherein the polypeptide comprises a sequence of about 25 to 200 amino acids wherein substantially all of the amino acids in said sequence are lysine; pharmaceutical compositions comprising said polypeptide or product and uses thereof.