2-乙酰基香豆酸 | 16189-10-9

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 中文名称: 2-乙酰基香豆酸
• 英文名称: (E)-3-<2-(acetyloxy)phenyl>-2-propenoic acid
• 英文别名: O-(E)-acetyl-o-coumaric acid；(E)-3-(2-acetoxyphenyl)acrylic acid；2-acetoxycinnamic acid；(2E)-3-[2-(acetyloxy)phenyl]prop-2-enoic acid；trans-2-Acetoxy-zimtsaeure；trans-o-Acetoxy-zimtsaeure；o-Acetylcoumarinic acid；Acetyl-o-cumarsaeure；o-Acetoxyzimtsaeure；2-acetoxy-trans-cinnamic acid；2-Acetoxy-trans-zimtsaeure；(E)-3-(2-acetyloxyphenyl)prop-2-enoic acid
• CAS: 16189-10-9
• 化学式: C₁₁H₁₀O₄
• 分子量: 206.198
• InChiKey: UXOWQQCLBQBRMQ-VOTSOKGWSA-N

物化性质

• 熔点：
  153-157 °C
• 沸点：
  367.5±25.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  2-乙酰基香豆酸 在 吡啶 、 氯化亚砜 作用下， 以 氯仿 为溶剂， 生成
  参考文献：
  名称：

  Characterization and quantitation of hexadecyl, octadecyl, and eicosyl esters of p-coumaric acid in the vine and root latex of sweetpotato [Ipomoea batatas (L.) Lam.]

  摘要：

  Methanol extracts of vine latex of four cultivars of sweetpotato [Ipomoea batatas (L.) Lam.] were analyzed for their chemical phenolic composition by reversed-phase HPLC. Major components were identified as hexadecyl, octadecyl, and eicosyl p-coumarates by an evaluation of data from UV spectra, hydrolysis, synthesis, and GC/MS of their trimethylsilyl derivatives. Both Z- and E-isomers of the phenolic acid were found, with the latter predominating. Trace quantities of hexadecyl (Z)- and (E)-ferulates were also identified in ester concentrates. Levels of octadecyl (E)-p-coumarate ranged from 0.7% fresh weight in cv. Resisto to almost 2% in cv. Jewel, while the hexadecyl ester levels were only 1/4 to 1/3 these values. Levels of the Z-esters were 1/10 to 1/20 of the levels of the corresponding E-isomers. Levels of the esters in cv. Jewel sweetpotato root latex were 2-10-fold the levels in the vine latex, while the ratio of E-esters to Z-esters was found to be 7-14-fold. The concentration of Z-esters among the sweetpotato cultivars tested correlated closely with the leaf feeding index for the sweetpotato weevil (Cylas formicarius) (R(2): C-20 = 0.96; C-18 = 0.98; C-16 = 0.71). The results indicate a possible relationship between latex chemistry and insect resistance that might be exploited via plant breeding.

  DOI：

  10.1021/jf00047a041
• 作为产物：
  描述：

  反式-2-羟基肉桂酸 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 生成 2-乙酰基香豆酸
  参考文献：
  名称：

  4-O-肉桂酰基奎尼基和sh草酸衍生物的新型酶促合成。

  摘要：

  通过用南极假丝酵母脂肪酶A进行区域选择性酯化反应，可以实现喹啉酸和sh草酸的4-O-肉桂酰基衍生物的首次直接合成。对于氢化肉桂酸酯，用乙烯基酯进行的酶促酯交换反应具有出色的收率。然而，使用更具反应性的酰化剂例如酸酐来合成两种酸的肉桂酸酯衍生物。观察到该脂肪酶对对甲氧基，对羟基和对乙酰氧基乙烯基酯和酸酐衍生物（香豆酸酯和阿魏酸酯衍生物）具有抑制作用。

  DOI：

  10.1021/jo034387a

文献信息

• [EN] COMPOUNDS AND COMPOSITIONS FOR OCULAR DELIVERY<br/>[FR] COMPOSÉS ET COMPOSITIONS POUR ADMINISTRATION OCULAIRE
  申请人：GRAYBUG VISION INC

  公开号：WO2020069353A1

  公开（公告）日：2020-04-02

  The present invention provides new prodrags of Sunitinib, Brinzolamide, and Dorzolamide and compositions to treat medical disorders, for example glaucoma, a disorder or abnormality related to an increase in intraocular pressure (TOP), a disorder requiring neuroprotection, age-related macular degeneration, or diabetic retinopathy.

  本发明提供了新的Sunitinib、Brinzolamide和Dorzolamide的前药，以及用于治疗医学疾病的组合物，例如青光眼、与眼内压增高有关的疾病或异常（TOP）、需要神经保护的疾病、年龄相关性黄斑变性或糖尿病视网膜病变。
• AMINO ACID DERIVATIVE
  申请人：Ookubo Tomohiro

  公开号：US20110172442A1

  公开（公告）日：2011-07-14

  The amino acid derivative of the present invention provides a novel compound that shows excellent analgesic action. The amino acid derivative of the present invention is a novel compound that shows excellent analgesic action to not only a model animal for nociceptive pains but also a model animal for neuropathic pains, so that the amino acid derivative is very useful as a drug for treating various pain diseases.

  本发明的氨基酸衍生物提供了一种显示出优异镇痛作用的新化合物。本发明的氨基酸衍生物是一种新化合物，不仅对于模拟伤害性疼痛的动物模型，而且对于模拟神经病理性疼痛的动物模型都显示出优异的镇痛作用，因此该氨基酸衍生物作为治疗各种疼痛疾病的药物非常有用。
• [EN] PRODRUGS OF KETAMINE, COMPOSITIONS AND USES THEREOF<br/>[FR] PROMÉDICAMENTS À BASE DE KÉTAMINE, COMPOSITIONS ET UTILISATIONS DE CEUX-CI
  申请人：XW LAB INC

  公开号：WO2019137381A1

  公开（公告）日：2019-07-18

  Provided are prodrugs of (S) -or (R) -ketamine, including isotopically labeled ketamine,composition and uses thereof. Compounds having formula (Ia) or (Ib) as the prodrugs of (S) -or (R) -ketamine, including isotopically labeled ketamine, and pharmaceutical compositions comprising the compounds provided herein are used for treating or preventing a CNS disease.More particularly, the related diseases include depression and pain. (Ia) (Ib)

  提供了（S）-或（R）-氯胺酮的前药，包括同位素标记的氯胺酮，其组成和用途。具有化学式（Ia）或（Ib）的化合物作为（S）-或（R）-氯胺酮的前药，包括同位素标记的氯胺酮，以及包含本文提供的化合物的药物组合物用于治疗或预防中枢神经系统疾病。更具体地，相关疾病包括抑郁症和疼痛。（Ia）（Ib）
• Modular Cyclopentenone Synthesis through the Catalytic Molecular Shuffling of Unsaturated Acid Chlorides and Alkynes
  作者：Yong Ho Lee、Elliott H. Denton、Bill Morandi

  DOI：10.1021/jacs.0c10832

  日期：2020.12.16

  general strategy for the intermolecular synthesis of polysubstituted cyclopentenones using palladium catalysis. Overall, this reaction is achieved via a molecular shuffling process involving an alkyne, an α,β-unsaturated acid chloride, which serves as both the alkene and carbon monoxide source, and a hydrosilane to create three new C-C bonds. This new carbon monoxide-free pathway delivers the products

  我们描述了使用钯催化分子间合成多取代环戊烯酮的一般策略。总体而言，该反应是通过涉及炔烃、α,β-不饱和酰氯（作为烯烃和一氧化碳来源）和氢硅烷的分子改组过程实现的，以产生三个新的 CC 键。这种新的无一氧化碳途径提供了具有优异产量的产品。此外，区域选择性是对环戊烯酮合成常规方法的补充。此外，还提出了一组区域和化学发散反应，以强调这种新策略的合成潜力。
• Synthesis of novel 1,2,5-oxadiazoles and evaluation of action against Acinetobacter baumannii
  作者：Rebecca M. Christoff、Gerald L. Murray、Xenia P. Kostoulias、Anton Y. Peleg、Belinda M. Abbott

  DOI：10.1016/j.bmc.2017.08.015

  日期：2017.12

  With multidrug resistant bacteria on the rise, novel antibiotics are becoming highly sought after. In 2008, eleven compounds were identified by high throughput screening as inhibitors of BasE, a key enzyme of the non-ribosomal peptide synthetase pathway found in Acinetobacter baumannii. Herein, we describe the preparation of four structurally similar heterocyclic lead compounds from that study, including

  随着对多种药物具有耐药性的细菌的兴起，新型抗生素正受到高度追捧。2008年，通过高通量筛选鉴定出11种化合物为BasE抑制剂，BasE是鲍曼不动杆菌中发现的非核糖体肽合成酶途径的关键酶。本文中，我们描述了该研究中四种结构相似的杂环铅化合物的制备方法，其中包括一种1,2,5-恶二唑。然后产生包含恶二唑部分的30种类似物的另一个文库。筛选了所有针对鲍曼不动杆菌的化合物，并报道了其最低抑菌浓度数据，其中包括（E）-3-（2-羟苯基）-N-（4-甲基-1,2,5-恶二唑-3-基）丙烯酰胺32发现MIC为0.5 mM。这项工作为进一步研究1,2,5-恶二唑作为鲍曼不动杆菌的新抑制剂提供了基础。

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