5-氯-4-羟基-2H-色烯-2-酮 | 54311-48-7

• 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: 5-氯-4-羟基-2H-色烯-2-酮
• 英文名称: 5-chloro-4-hydroxycoumarin
• 英文别名: 5-Chloro-4-hydroxy-2H-chromen-2-one；5-chloro-4-hydroxychromen-2-one
• CAS: 54311-48-7
• 化学式: C₉H₅ClO₃
• mdl: MFCD08234778
• 分子量: 196.59
• InChiKey: IEAZCJCNBVWFII-UHFFFAOYSA-N

物化性质

• 沸点：
  389.6±42.0 °C(Predicted)
• 密度：
  1.585±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  5-氯-4-羟基-2H-色烯-2-酮 在 盐酸 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 4.5h， 生成 4-(3-aminopropoxy)-5-chloro-1-benzopyran-2-one hydrochloride
  参考文献：
  名称：

  Design, synthesis and characterization of a novel class of coumarin-based inhibitors of inducible nitric oxide synthase

  摘要：

  Inducible nitric oxide synthase (iNOS) has been implicated in various central and peripheral pathophysiological diseases. Our high throughput screening initially identified a weak inhibitor of iNOS, thiocoumarin 13. From this lead, a number of potent derivatives were prepared that demonstrate favorable potency, selectivity and kinetics. Compound 30 has an IC50 of 60 nM for mouse iNOS and 185-fold and 9-fold selectivity for bovine eNOS and rat nNOS, respectively. In cellular assays for iNOS, this compound has micromolar potency. Furthermore, two compounds (16 and 30) demonstrate a reasonable pharmacokinetic profile in rodents. The synthesis, SAR, and biological activity of this novel class of compounds is described.

  DOI：

  10.1016/j.bmc.2005.02.036
• 作为产物：
  描述：

  2-acetyl-3-chlorophenyl diethylcarbamate 在 sodium hydride 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 生成 5-氯-4-羟基-2H-色烯-2-酮
  参考文献：
  名称：

  Directed ortho metalation - cross coupling links. Carbamoyl rendition of the baker-venkataraman rearrangement. Regiospecific route to substituted 4-hydroxycoumarins

  摘要：

  A new carbamoyl Baker-Venkataraman rearrangement (4) which allows a general synthesis of substituted 4-hydroxycoumarins 8 in 43-82% overall yields is described; the intermediate arylketones 6 are efficiently prepared (59-91% yields) via a Directed ortho Metalation - Negishi cross coupling protocol from arylcarbamates 5 and the overall sequence provides a regiospecific anionic Friedel-Crafts complement for the construction of ortho-acyl phenols and coumarins. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00977-0

文献信息

• Lewis Acid‐Catalyzed Formal [3+3] Annulation of Propargylic Alcohols with 4‐Hydroxy‐2 <i>H</i> ‐chromen‐2‐ones
  作者：Ya‐Ping Han、Xue‐Song Li、Ming Li、Xin‐Yu Zhu、Yong‐Min Liang

  DOI：10.1002/adsc.201800131

  日期：2018.8.6

  tricyclic compounds possessing functionalized pyrano[3,2‐c]chromen‐5(2H)‐one fragments has been developed using propargylic alcohols and 4‐hydroxy‐2H‐chromen‐2‐ones as the substrates. The protocol provides a one‐step, environmentally benign method of accessing a broad range of pyrano[3,2‐c]chromen‐5(2H)‐one derivatives in excellent yields under mild conditions and with good functional‐group tolerance. The method

  一种路易斯酸催化的正式[3 + 3]级联环化策略，用于形成具有官能化吡喃并[3,2-c] chromen-5（2 H）-一个片段的各种三环化合物，已使用炔丙醇和4-羟基2 H-铬2-2作为底物。该协议提供了一种在环境温和的条件下以良好的收率和良好的官能团耐受性来访问范围广泛的吡喃并[3,2-c] chromen-5（2 H）-one衍生物的一步法，对环境无害的方法。该方法在克规模上是有效的，这突出了这种合成转化的固有实用性。
• Alcohol Mediated Synthesis of 4-Oxo-2-aryl-4<i>H</i>-chromene-3-carboxylate Derivatives from 4-Hydroxycoumarins
  作者：Manoj R. Zanwar、Mustafa J. Raihan、Sachin D. Gawande、Veerababurao Kavala、Donala Janreddy、Chun-Wei Kuo、Ram Ambre、Ching-Fa Yao

  DOI：10.1021/jo301044y

  日期：2012.8.3

  The unusual alcohol mediated formation of 4-oxo-2-aryl-4H-chromene-3-carboxylate (flavone-3-carboxylate) derivatives from 4-hydroxycoumarins and β-nitroalkenes in an alcoholic medium is described. The transformation occurs via the in situ formation of a Michael adduct, followed by the alkoxide ion mediated rearrangement of the intermediate. The effect of the different alcohol and nonalcohol media on

  这种不寻常的醇介导的4-氧代-2-芳基-4-的形成ħ色烯-3-羧酸甲酯（黄酮-3-羧酸）衍生物由4-羟基香豆素和β-硝基烯烃在醇介质进行说明。该转化通过原位形成迈克尔加合物而发生，随后是醇盐离子介导的中间体重排。研究了不同醇和非醇介质对反应的影响。
• CFL light promoted one-pot synthesis of pyrano[3,2-<i>c</i>]chromen-5(4<i>H</i>)-ones
  作者：Ankusab Noorahmadsab Nadaf、Kalegowda Shivashankar

  DOI：10.1080/00397911.2018.1426101

  日期：2018.4.3

  ABSTRACT An eco-friendly synthesis of pyrano[3,2-c]chromen-5(4H)-one derivatives was conducted by the condensation of 4-hydroxycoumarins, aromatic aldehydes, and acetophenones. Clean profile, excellent yield, ambient temperature, and use of visible light intensity instead of catalyst are the attractive features of this method. GRAPHICAL ABSTRACT

  摘要 通过 4-羟基香豆素、芳香醛和苯乙酮的缩合，进行了吡喃并[3,2-c]色烯-5(4H)-one 衍生物的环保合成。干净的轮廓、出色的产量、环境温度和使用可见光强度代替催化剂是这种方法的吸引人的特点。图形概要
• Coumarins as iNOS inhibitors
  申请人：Jackson Sharon

  公开号：US20050054681A1

  公开（公告）日：2005-03-10

  The present invention relates to coumarins of the formula (I): that are useful as inhibitors of nitric oxide synthase. Pharmaceutical compositions and methods of using these compounds as inhibitors of nitric oxide synthase are described herein.

  本发明涉及一种具有以下结构的香豆素（I）：这些化合物可作为一氧化氮合酶的抑制剂。本文描述了这些化合物作为一氧化氮合酶抑制剂的药物组合物和使用方法。
• Does chlorination modify the auxin-like activity of 1,2-benzisoxazole-3-acetic acid?
  作者：Camillo Branca、Ada Ricci、Anna Torelli、Cesare A. Maggiali、Ferdinando Ronchini、Maria Bassi

  DOI：10.1016/0031-9422(93)85203-4

  日期：1993.3

  Abstract The insertion of a chlorine atom in different positions of the aromatic ring did not increase the activity of benzisoxazole acetic acid, a new syntheti

  摘要 在芳环的不同位置插入一个氯原子并没有增加苯并异恶唑乙酸的活性，苯并异恶唑乙酸是一种新的合成物。