3-formyl-2-hydroxyacetophenone | 55108-29-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-formyl-2-hydroxyacetophenone
• 英文别名: 3-acetyl salicylaldehyde；Benzaldehyde, 3-acetyl-2-hydroxy-；3-acetyl-2-hydroxybenzaldehyde
• CAS: 55108-29-7
• 化学式: C₉H₈O₃
• 分子量: 164.161
• InChiKey: OPPZJAAVEDSDPQ-UHFFFAOYSA-N

物化性质

• 熔点：
  260 °C
• 沸点：
  255.8±25.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-formyl-2-hydroxyacetophenone 在 sodium acetate 、 乙酸酐 作用下， 生成 香豆素
  参考文献：
  名称：

  Perkin, Journal of the Chemical Society, 1868, vol. 21, p. 185

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(3-烯丙基-2-羟基苯基)乙酮 在 二(氰基苯)二氯化钯 、 二甲基硫 、 臭氧 作用下， 以 甲苯 为溶剂， 反应 35.0h， 生成 3-formyl-2-hydroxyacetophenone
  参考文献：
  名称：

  Synthesis and quantitative structure-activity relationships of antiallergic 2-hydroxy-N-(1H-tetrazol-5-yl)benzamides and N-(2-hydroxyphenyl)-1H-tetrazole-5-carboxamides

  摘要：

  The synthesis and antiallergic activity of a series of 2-hydroxy-N-1H-tetrazol-5-ylbenzamides and isomeric N-(2-hydroxyphenyl)-1H-tetrazole-5-carboxamides is described. A relationship between structure and intravenous antiallergic activity in the rat passive cutaneous anaphylaxis (PCA) test has been established using a Hansch/Free-Wilson model and used to direct studies toward potent derivatives. The contribution of physicochemical properties to activity is discussed. One member of this series, N-(3-acetyl-5-fluoro-2-hydroxyphenyl)-1H-tetrazole-5-carboxamide (3f), which was selected for further evaluation, has an ID50 value of 0.16 mg/kg po and is 130 times more potent than disodium cromoglycate (DSCG) on intravenous administration.

  DOI：

  10.1021/jm00154a019

文献信息

• Benzamide derivatives
  申请人：May & Baker Limited

  公开号：US04146631A1

  公开（公告）日：1979-03-27

  Benzamide derivatives of the formula:- ##STR1## wherein R.sup.1 represents a fluorine, chlorine or bromine atom, or an alkyl, alkoxy, alkylthio, alkylsulphonyl, alkanoylamino, alkylamino or alkylsulphamoyl group, each such group containing from 1 to 6 carbon atoms, a dialkylsulphamoyl, dialkylamino or dialkylcarbamoyl group (wherein the two alkyl groups may be the same or different and each contains from 1 to 4 carbon atoms), an alkanoyl, alkoxycarbonyl, alkoxycarbonylamino or alkylcarbamoyl group containing from 2 to 6 carbon atoms, or a hydroxy, formyl, nitro, trifluoromethyl, aryl, benzyloxycarbonylamino, amino, sulphamoyl, cyano, tetrazol-5-yl, carboxy, carbamoyl or aroyl group, and n represents an integer 1, 2 or 3, are new compounds possessing pharmacological properties, in particular properties of value in the treatment of respiratory disorders manifested by the interaction of tissue-fixed antibodies with specific antigens.

  苯甲酰胺衍生物的化学式为：- ##STR1## 其中R.sup.1代表氟、氯或溴原子，或烷基、烷氧基、烷硫基、烷磺酰基、烷酰胺基、烷基胺基或烷基磺酰胺基，每个这样的基团含有1至6个碳原子，双烷基磺酰胺基、双烷基胺基或双烷基氨基甲酰基（其中两个烷基可能相同或不同，每个含有1至4个碳原子），含有2至6个碳原子的烷酰基、烷氧羰基、烷氧羰胺基或烷基氨基甲酰基，或羟基、甲酰基、硝基、三氟甲基、芳基、苄氧羰胺基、氨基、磺酰胺基、氰基、四唑-5-基、羧基、氨基甲酰基或芳酰基，n代表整数1、2或3，是具有药理特性的新化合物，特别是在治疗由组织固定抗体与特定抗原相互作用所表现出的呼吸系统疾病的治疗中具有价值的特性。
• Acetamide/SO2Cl2 as an efficient reagent for Friedel–Craft’s acylation of aromatic compounds under ultrasonic and microwave conditions
  作者：Mukka Satish Kumar、Kamatala Chinna Rajanna、Purugula Venkanna、Marri Venkateswarlu

  DOI：10.1016/j.tetlet.2014.01.099

  日期：2014.3

  developed for effective Friedel–Craft’s acylation of aromatic compounds. Acylation of aromatic compounds with acetamide/SO2Cl2 was much more effective and faster than analogous (acetamide/SOCl2) and (acetamide/POCl3) reagents even under conventional conditions. However, microwave and ultrasonic assisted reactions afforded high yields of products in very short reaction times (30–40 min under sonication and 3–4 min

  已开发出乙酰胺/ SO 2 Cl 2试剂，用于有效地进行Friedel-Craft芳族化合物的酰化反应。即使在常规条件下，与类似的（乙酰胺/ SOCl 2）和（乙酰胺/ POCl 3）试剂相比，用乙酰胺/ SO 2 Cl 2酰化芳族化合物也更有效和更快。但是，微波和超声辅助反应可在非常短的反应时间内（在超声处理下30–40分钟，在微波辅助条件下3-4分钟）提供高产率的产品。
• COUMARIN DERIVATIVE AND USE THEREOF
  申请人：MORINAGA MILK INDUSTRY CO., LTD.

  公开号：EP0645382A1

  公开（公告）日：1995-03-29

  The invention provides a compound having a 12-lipoxygenase inhibitory effect and a drug selectively inhibiting 12-lipoxygenase and relates to a novel coumarin derivative represented by general formula (1) and a drug comprising said compound as the active ingredient. In formula (1) R¹ represents hydrogen or lower alkyl; R² and R³ represent each hydrogen or hydroxyl provided that R² and R³ do not represent hydrogen atoms at the same time; and Ar represents (a) (b), (c) etc.; and R⁴ represents lower alkyl, lower alkoxy, halogen, trifluoromethyl or cyano. It further provides a compound which can be converted into another compound capable of selectively inhibiting 12-lipoxygenase activity through cleavage and breakage of its modifying moiety in vivo and a drug which selectively inhibits 12-lipoxygenase and relates to a novel coumarin derivative having an acyl group as the modifying moiety and a drug containing said compound as the active ingredient. The invention compound, which can potently inhibit 12-lipoxygenase at a high selectivity, is useful as a drug for preventing and treating circulatory diseases such as arteriosclerosis and vasoconstriction and preventing the metastasis of certain cancers. It has a low toxicity and little exhibits side effects.

  本发明提供了一种具有12-脂氧合酶抑制作用的化合物和一种选择性抑制12-脂氧合酶的药物，并涉及一种由通式(1)表示的新型香豆素衍生物和一种以上述化合物为活性成分的药物。在式(1)中，R¹代表氢或低级烷基；R²和R³分别代表氢或羟基，条件是R²和R³不同时代表氢原子；Ar代表(a)(b)、(c)等；R⁴代表低级烷基、低级烷氧基、卤素、三氟甲基或氰基。本发明进一步提供了一种化合物，该化合物可通过其修饰基团在体内的裂解和断裂转化为另一种能够选择性抑制 12-脂氧合酶活性的化合物，以及一种选择性抑制 12-脂氧合酶的药物，并涉及一种以酰基为修饰基团的新型香豆素衍生物和一种含有上述化合物作为活性成分的药物。本发明化合物能以高选择性有效抑制 12-脂氧合酶，可用作预防和治疗动脉硬化和血管收缩等循环系统疾病以及防止某些癌症转移的药物。它毒性低，副作用小。
• [EN] METHOD FOR PREPARING THYMALFASIN<br/>[FR] PROCÉDÉ DE PRÉPARATION DE THYMALFASINE<br/>[ZH] 一种制备胸腺法新的方法
  申请人：HYBIO PHARMACEUTICAL CO LTD

  公开号：WO2020124975A1

  公开（公告）日：2020-06-25

  公开了一种制备胸腺法新的方法，采用乙酰水杨醛或乙酰水杨醛类似物对胸腺法新28肽进行选择性N-端乙酰化制备胸腺法新。所述方法不需要对胸腺法新28肽的其它氨基进行保护，避免了其它乙酰化方法需要的对赖氨酸侧链氨基进行特殊保护会用到的昂贵原料以及繁琐的脱除操作。
• The Reactions of Ketene with Salicylaldehyde and p-Hydroxybenzaldehyde
  作者：Jonathan W. Williams、Alexander Sadle

  DOI：10.1021/ja01867a049

  日期：1940.10