5-氯水杨酸乙酯 | 15196-83-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-氯水杨酸乙酯
• 中文别名: 乙基5-氯-2-羟基苯酸酯
• 英文名称: ethyl 5-chloro-2-hydroxybenzoate
• 英文别名: 5-chlorosalicylic acid ethyl ester；Ethyl 5-chlorosalicylate
• CAS: 15196-83-5
• 化学式: C₉H₉ClO₃
• mdl: MFCD06204295
• 分子量: 200.622
• InChiKey: ATMSMRINTOGATK-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于氯仿、可溶于二氯甲烷、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-氯水杨酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以70%的产率得到5-氯-2-羟基苯甲酰肼
  参考文献：
  名称：

  发现基于靛红的碳腙作为脂肪酸酰胺水解酶和单酰基甘油脂肪酶的潜在双重抑制剂

  摘要：

  使用基于配体的设计策略，设计、合成了一组 isatin-3-carbohydrazone，并评估了它们的双重 FAAH-MAGL 抑制特性。该研究提供了一种有效的双重 FAAH-MAGL 抑制剂 ( 13 c ) 和一种选择性 MAGL 抑制剂 ( 13 b )，具有可接受的药代动力学特征。这些化合物可以被认为是治疗神经疾病的有希望的候选者。

  DOI：

  10.1002/cmdc.202100559
• 作为产物：
  描述：

  3-氯苯甲酸乙酯 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 Selectfluor 、 三氟乙酸 、 三氟乙酸酐 作用下， 反应 10.0h， 以53%的产率得到5-氯水杨酸乙酯
  参考文献：
  名称：

  Ruthenium(II)-Catalyzed Synthesis of Hydroxylated Arenes with Ester as an Effective Directing Group

  摘要：

  An unprecedented Ru(II) catalyzed ortho-hydroxylation has been developed for the facile synthesis of a variety of multifunctionalized arenes from easily accessible ethyl benzoates with ester as an efficient directing group. Both the TFA/TFAA cosolvent system and oxidants serve as the critical success factors in this transformation. The reaction demonstrates excellent reactivity, good functional group tolerance, and high yields.

  DOI：

  10.1021/ol301104n

文献信息

• Synthesis and evaluation of antitumour activity <i>in vitro</i> and <i>in vivo</i> of chrysin salicylate derivatives
  作者：Xiangping Deng、Zihao Zhao、Shujuan Xiong、Runde Xiong、Juan Liu、Zhe Wang、Liu Zou、Xiaoyong Lei、Xuan Cao、Zhizhong Xie、Yanming Chen、Xing Zheng、Yunmei Liu、Guotao Tang

  DOI：10.1080/14786419.2017.1371159

  日期：2018.9.17

  A series of chrysin salicylate derivatives as potential antitumour agents were synthesised and evaluated their antitumour activities in vitro and in vivo. Most of the compounds exhibited moderate to good activities against MCF-7 cells, HepG2 cells, MGC-803cells and MFC cells. Among them, compound 3f showed the most potent activity against MGC-803 cells and MFC cells with IC50 values of 23.83 ± 3.68

  一系列白杨素水杨酸酯衍生物作为潜在的抗肿瘤剂的合成和评价了它们的抗肿瘤活性在体外和体内。大多数化合物对MCF-7细胞，HepG2细胞，MGC-803细胞和MFC细胞表现出中等至良好的活性。其中，化合物3f对MGC-803细胞和MFC细胞表现出最强的活性，IC 50值分别为23.83±3.68和27.34±5.21μM。流式细胞仪分析再次确认，化合物3F促进肿瘤细胞G1 /化合物的抑制作用下S嵌段的发生3F。化合物3f 与阳性对照5-Fu和空白对照盐水相比，荷瘤小鼠具有更高的抗肿瘤功效。
• Overcoming the Deallylation Problem: Palladium(II)-Catalyzed Chemo-, Regio-, and Stereoselective Allylic Oxidation of Aryl Allyl Ether, Amine, and Amino Acids
  作者：Kartic Manna、Hasina Mamataj Begam、Krishanu Samanta、Ranjan Jana

  DOI：10.1021/acs.orglett.0c02465

  日期：2020.10.2

  We report herein a Pd(II)/bis-sulfoxide-catalyzed intramolecular allylic C–H acetoxylation of aryl allyl ether, amine, and amino acids with the retention of a labile allyl moiety. Mechanistically, the reaction proceeds through a distinct double-bond isomerization from the allylic to the vinylic position followed by intramolecular carboxypalladation and the β-hydride elimination pathway. For the first

  我们在此报告了芳基烯丙基醚，胺和氨基酸的Pd（II）/双亚砜催化的分子内烯丙基CH乙酰氧基化，同时保留了不稳定的烯丙基部分。从机理上讲，反应是通过从烯丙基位置到乙烯基位置的独特的双键异构化进行的，然后进行分子内羧基palpalpalation和β-氢化物消除途径。首次建立了具有出色的非对映选择性的N-烯丙基保护氨基酸的C–H氧化，可通过1,3-syn加成提供五元杂环。
• Isoxazole derivatives
  申请人：Sankyo Company, Limited

  公开号：US05965591A1

  公开（公告）日：1999-10-12

  An isoxazole compound having the following formula: wherein R.sup.1 represents hydrogen, halogen, alkyl, alkoxy, hydroxyl, alkylthio, amino, alkanoyl, alkanoylamino, alkanoyloxy, alkoxycarbonyl, carboxy, (alkylthio)thiocarbonyl, carbamoyl, nitro or cyano; R.sup.2 represents an amino; m is 1; n is 1 to 6; ring A represents a phenyl ring or a naphthyl ring; and X represents oxygen or sulfur. The isoxazole compound has an excellent monoamine oxidase inhibitory activity, and is useful for treating Parkinson's disease, depression and Alzheimer's disease.

  一种异噁唑化合物具有以下结构式：其中R.sup.1代表氢、卤素、烷基、烷氧基、羟基、烷硫基、氨基、烷酰基、烷酰胺基、烷酰氧基、烷氧羰基、羧基、(烷硫基)硫代羰基、氨基甲酰基、硝基或氰基；R.sup.2代表氨基；m为1；n为1至6；环A代表苯环或萘环；X代表氧或硫。该异噁唑化合物具有出色的单胺氧化酶抑制活性，可用于治疗帕金森病、抑郁症和阿尔茨海默病。
• [4H]-1,3-Benzodioxin-2-carboxylic acids
  申请人：Roussel Uclaf

  公开号：US04281012A1

  公开（公告）日：1981-07-28

  Novel racemates and optically active isomers and mixtures of isomers of [4H]-1,3-benzodioxin-2-carboxylic acid compounds of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen, alkyl of 1 to 5 carbon atoms, dialkylamino alkyl with alkyls of 1 to 5 carbon atoms, alkali metal, alkaline earth metal, aluminum, --NH.sub.4, non-toxic pharmaceutically acceptable amines, 2,3-dihydroxypropanyl and (2,2-dimethyl-1,3-dioxolan-4-yl)-methyl, R.sub.2 is selected from the group consisting of hydrogen and alkyl of 1 to 5 carbon atoms, R.sub.3 and R.sub.6 are individually selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms, ethenyl and cyclohexyl and taken together with the carbon atom to which they are attached form cyclohexyl, R.sub.5 is selected from the group consisting of hydrogen and halogen or R.sub.1 and R.sub.2 have the above definitions, R.sub.6 is ##STR2## R.sub.4 and R.sub.5 are individually selected from the group consisting of hydrogen, halogen, --CF.sub.3, cyclohexyl, alkoxy of 1 to 3 carbon atoms, alkyl of 1 to 3 carbon atoms and p-chlorophenoxy and R.sub.3 is selected from the group consisting of 2-propenyl, ethenyl, cyclohexyl, benzyl, hydrogen and alkyl of 1 to 5 carbon atoms with the proviso that when R.sub.3 is alkyl, at least one of R.sub.4 and R.sub.5 is no hydrogen or halogen and when R.sub.3 is hydrogen, at least one of R.sub.4 and R.sub.5 is not hydrogen, halogen or --CF.sub.3 and the non-toxic, pharmaceutically acceptable acid addition salts thereof when R.sub.1 is dialkylaminoalkyl which have a marked hypolipemiant activity and reduces the plasmatic level of lipids, triglycerides and cholestrol and their preparation.

  新的外消旋体和光学活性异构体以及[4H]-1,3-苯并二氧杂环戊二酸化合物的混合物，其化学式为##STR1##其中R.sub.1选自由氢、1至5个碳原子的烷基、烷基为1至5个碳原子的二烷基氨基烷基、碱金属、碱土金属、铝、--NH.sub.4、无毒的药学可接受胺、2,3-二羟基丙基和(2,2-二甲基-1,3-二氧杂环戊-4-基)-甲基，R.sub.2选自由氢和1至5个碳原子的烷基，R.sub.3和R.sub.6分别选自由氢、1至6个碳原子的烷基、乙烯基和环己基，并与它们连接的碳原子形成环己基，R.sub.5选自由氢和卤素或R.sub.1和R.sub.2具有上述定义，R.sub.6为##STR2##R.sub.4和R.sub.5分别选自由氢、卤素、--CF.sub.3、环己基、1至3个碳原子的烷氧基、1至3个碳原子的烷基和对氯苯氧基，R.sub.3选自2-丙烯基、乙烯基、环己基、苄基、氢和1至5个碳原子的烷基，但要求当R.sub.3为烷基时，至少一个R.sub.4和R.sub.5不是氢或卤素，当R.sub.3为氢时，至少一个R.sub.4和R.sub.5不是氢、卤素或--CF.sub.3，以及其非毒性、药学可接受的酸盐，当R.sub.1为二烷基氨基烷基时，具有明显的降脂活性，降低血浆中脂质、三酸甘油脂和胆固醇的水平，以及它们的制备。
• 3-Propionylsalicylic acid derivatives and process for the preparation of
  申请人：Yamamoto Chemical Industrial Company, Limited

  公开号：US04533732A1

  公开（公告）日：1985-08-06

  This invention relates to derivatives of 3-propionylsalicylic acid represented by the formula (1) ##STR1## wherein R represents a hydrogen atom, a lower alkyl group or a group ##STR2## (wherein R.sup.1 and R.sup.2 represent a lower alkyl group or R.sup.1 and R.sup.2, when taken together with the nitrogen atom to which they are attached, may form a heterocyclic ring with or without an intervening hetero atom, and n is an integer of 1 to 4), and X represents a hydrogen atom or a halogen atom, R being the group ##STR3## when X is a hydrogen atom. This invention also relates to processes for preparing the same.

  这项发明涉及由式（1）表示的3-丙酰基水杨酸衍生物，其中R代表氢原子、较低的烷基基团或基团（其中R.sup.1和R.sup.2代表较低的烷基基团或R.sup.1和R.sup.2，当它们与它们连接的氮原子一起时，可形成带有或不带有介入杂原子的杂环环，n为1至4的整数），X代表氢原子或卤原子，当X为氢原子时，R为基团##STR3##。这项发明还涉及制备这些衍生物的方法。