5-methylcoumarin | 42286-84-0

• 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: 5-methylcoumarin
• 英文别名: 5-methyl-2H-chromen-2-one；5-methylchromone；5-methylchromen-2-one
• CAS: 42286-84-0
• 化学式: C₁₀H₈O₂
• mdl: MFCD01731763
• 分子量: 160.172
• InChiKey: FXMGSXNQELBPMX-UHFFFAOYSA-N

物化性质

• 熔点：
  65.8°C
• 沸点：
  246.06°C (rough estimate)
• 密度：
  1.0924 (rough estimate)
• LogP：
  1.850 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  5-methylcoumarin 在 phosphorous (V) sulfide 作用下， 生成 5-methyl-chromene-2-thione
  参考文献：
  名称：

  Nakabayashi, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1954, vol. 74, p. 895,896

  摘要：

  DOI：
• 作为产物：
  描述：

  5-methyl-2-oxo-2H-chromene-3-carboxylic acid 生成 5-methylcoumarin
  参考文献：
  名称：

  Chuit; Bolsing, Bulletin de la Societe Chimique de France, 1906, vol. <3> 35, p. 88

  摘要：

  DOI：

文献信息

• Visible-light promoted oxidative cyclization of cinnamic acid derivatives using xanthone as the photocatalyst
  作者：Bin Zhao、Bo Xu

  DOI：10.1039/d0ob02417a

  日期：——

  coumarin derivatives via a tandem double bond isomerization/oxidative cyclization of cinnamic acids. Inexpensive and stable xanthone was used as the photocatalyst, and readily available Selectfluor was used as the oxidant. This method tolerates a wide range of functional groups and offers excellent chemical yields in general. Besides, the photocatalytic oxidative cyclization of cinnamic acid esters gives

  我们已经通过肉桂酸的串联双键异构化/氧化环化开发了一种香豆素衍生物的有效光催化合成方法。廉价，稳定的x吨酮用作光催化剂，易购的Selectfluor用作氧化剂。该方法可耐受各种官能团，并且通常可提供出色的化学收率。此外，肉桂酸酯的光催化氧化环化得到二聚的木脂素型产物。
• Diarylalkanes as potent inhibitors of binuclear enzymes
  申请人：Jia Qi

  公开号：US20050267047A1

  公开（公告）日：2005-12-01

  The present invention implements a strategy that combines an enzyme inhibition assay with a chemical dereplication process to identify active plant extracts and the particular compounds—diarylalkanes and/or diarylalkanols within those extracts that specifically inhibit binuclear enzyme function. Included in the present invention are compositions of matter comprised of one or more of diarylalkanes and/or diarylalkanols, which inhibit the activity of binuclear enzymes, particularly tyrosinase and which prevent melanin overproduction. The present invention also provides a method for inhibiting the activity of a binuclear enzyme, particularly tyrosinase and a method for preventing and treating diseases and conditions related to binuclear enzyme function. The present invention further includes a method for preventing and treating melanin overproduction and diseases and conditions of the skin related thereto. The method for preventing and treating diseases and conditions related to binuclear enzyme function and melanin overproduction is comprised of administering to a host in need thereof an effective amount of a composition comprising one or more diarylalkanes and/or diarylalkanols synthesized and/or isolated from one or more plants together with a pharmaceutically acceptable carrier.

  本发明实施了一种策略，将酶抑制测定与化学去重复过程相结合，以识别活性植物提取物和特定化合物——二芳基烷烃和/或二芳基醇，这些化合物特异性地抑制双核酶功能。本发明包括由一种或多种二芳基烷烃和/或二芳基醇组成的物质组合物，其抑制双核酶的活性，特别是酪氨酸酶，并防止黑色素过度产生。本发明还提供了一种抑制双核酶活性的方法，特别是酪氨酸酶，以及一种预防和治疗与双核酶功能相关的疾病和病况的方法。本发明还包括一种预防和治疗黑色素过度产生以及与之相关的皮肤疾病和病况的方法。预防和治疗与双核酶功能和黑色素过度产生相关的疾病和病况的方法包括向需要的宿主施用由一种或多种植物合成和/或分离的一种或多种二芳基烷烃和/或二芳基醇组成的组合物的有效量，以及药用载体。
• Metal‐free, Visible‐Light‐Mediated Direct Csp ² −H Radical Mono‐ and Bis‐trifluoromethylation of Coumarins and Bioactivity Evaluation
  作者：Xiang Yu、Peng Dai、Yu‐Chuan Zhu、Peng Teng、Wei‐Hua Zhang、Chao Deng

  DOI：10.1002/cctc.201801332

  日期：2018.11.22

  A clean, transition metal‐ and oxidant‐free photochemical protocol was described for the direct trifluoromethylation of coumarins with Togni reagent. The reaction proceeded smoothly under mild condition to afford regioselective 3‐trifluoromethyl coumarins, moreover novel bis‐trifluoromethylated coumarins were formed. Preliminary bioactivity evaluation on some products showed potential antifungal activities

  描述了使用Togni试剂对香豆素进行直接三氟甲基化的清洁，无过渡金属和氧化剂的光化学方案。反应在温和的条件下平稳进行，得到区域选择性的3-三氟甲基香豆素，而且形成了新型的双三氟甲基化香豆素。对某些产品的初步生物活性评估显示出潜在的抗真菌活性。
• Synthesis of coumarins by Pt-catalyzed hydroarylation of propiolic acids with phenols
  作者：Juzo Oyamada、Tsugio Kitamura

  DOI：10.1016/j.tet.2006.04.080

  日期：2006.7

  Synthesis of coumarins from phenols and propiolic acids was examined by using a Pt catalyst such as PtCl2/AgOTf, K2PtCl4/AgOTf, and K2PtCl4/AgOAc. Propiolic acid reacted even with less reactive phenols in trifluoroacetic acid to give coumarins and dihydrocoumarins. In the case of substituted propiolic acids, phenylpropiolic acid and 2-octynoic acid, the reactions proceeded selectively to afford coumarins

  通过使用Pt催化剂如PtCl 2 / AgOTf，K 2 PtCl 4 / AgOTf和K 2 PtCl 4 / AgOAc检查由酚和丙酸合成香豆素。丙酸甚至在三氟乙酸中与反应性较低的酚发生反应，得到香豆素和二氢香豆素。在取代的丙酸，苯丙酸和2-辛酸的情况下，反应选择性地进行，从而以高收率或高收率获得香豆素。
• Metal-free, Brønsted acid-mediated synthesis of coumarin derivatives from phenols and propiolic acids
  作者：Hyuck Choi、Jaehyun Kim、Kooyeon Lee

  DOI：10.1016/j.tetlet.2016.06.039

  日期：2016.8

  A novel synthesis of coumarin derivatives by Brønsted acid-mediated condensation and intramolecular cyclization of phenols and propiolic acids was reported. This transformation requires the use of TfOH in place of a conventional metal mediator, and it occurs under mild conditions and provides rapid access to coumarin derivatives in good yields.

  报道了通过布朗斯台德酸介导的缩合和酚和丙酸的分子内环化的香豆素衍生物的新颖合成。这种转变需要使用TfOH代替传统的金属介体，并且它在温和的条件下发生，并以高收率快速提供香豆素衍生物。