α-hydroxy-3-cyanoacetophenone | 83112-50-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-hydroxy-3-cyanoacetophenone
• 英文别名: 3-(2-hydroxyacetyl)benzonitrile
• CAS: 83112-50-9
• 化学式: C₉H₇NO₂
• mdl: MFCD24141517
• 分子量: 161.16
• InChiKey: RPDWLOIHBKPAIE-UHFFFAOYSA-N

物化性质

• 沸点：
  330.6±22.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-hydroxy-3-cyanoacetophenone 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以86%的产率得到3-(1,2-dihydroxyethyl)benzonitrile
  参考文献：
  名称：

  Synthesis of 3-Substituted Benzamides and 5-Substituted Isoquinolin-1(2H)-ones and Preliminary Evaluation as Inhibitors of Poly(ADP-ribose)polymerase (PARP)

  摘要：

  Inhibitors of poly(ADP-ribose)polymerase (PARP) inhibit repair of damaged DNA and thus potentiate radiotherapy and chemotherapy of cancer. 3-Substituted benzamides and 5-substituted isoquinolin-1-ones have been synthesised and evaluated for inhibition of PARP. Reduction of 3-(bromoacetyl)benzamide, followed by treatment with base, gave RS-3-oxiranylbenzamide. Reduction of 3-(hydroxyacetyl)benzonitrile with bakers' yeast gave 'the R-diol which was converted to R-3-(1,2-dihydroxyethyl)benzamide. Similar reduction of 3-(acetoxyacetyl)benzonitrile led towards the S-diol which was converted to its cyclic acetonide. E-2-(2,6-Dicyanophenyl)-N,N-dimethylethenamine was formed by condensation of 2,6-dicyanotoluene with dimethylformamide dimethyl acetal (DMFDMA); cyclisation under acidic conditions afforded 5-cyanoisoquinolin-1-one. Heck coupling of 5-iodoisoquinolin-1-one with propenoic acid formed E-3-(1-oxoisoquinolin-5-yl)propenoic acid. 3-Oxiranylbenzamide, 5-bromoisoquinolin-1-one and 5-iodoisoquinolin-1-one were among the most potent inhibitors of PARP activity in a preliminary screen in vitro. (C) 1998 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00029-7
• 作为产物：
  描述：

  α-acetoxy-3-cyanoacetophenone 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 以61%的产率得到α-hydroxy-3-cyanoacetophenone
  参考文献：
  名称：

  Synthesis of α-Hydroxyacetophenones

  摘要：

  A general method for the preparation of alpha-hydroxyacetophenones is presented. Functionalized arylmagnesium species are transmetalated to the corresponding arylzinc intermediates, which undergo Cu(I)-catalyzed reaction with acetoxyacetyl chloride. Acidic hydrolysis of the acetate group releases the target alpha-hydroxyacetophenones with minimal production of undesired polymeric degradates that are often observed under alternative conditions.

  DOI：

  10.1021/jo3005556

文献信息

• Direct Aerobic Oxidative Reactions of 2-Hydroxyacetophenones
  作者：Subas Chandra Sahoo、Utpal Nath、Subhas Chandra Pan

  DOI：10.1002/ejoc.201700909

  日期：2017.8.17

  Metal-free and external-oxidant-free aerobic oxidative reactions of 2-hydroxyacetophenones are developed. The reactions are based on the aerobic formation of small equilibrium quantities of 2-keto aldehydes. Phthalides, quinoxalines, α-keto amides, and olefins can be formed in moderate to good yields directly from alcohols. DIPEA = diisopropylethylamine.

  开发了2-羟基苯乙酮的无金属和无外部氧化剂的好氧氧化反应。该反应是基于有氧形成少量的2-酮醛的平衡量。邻苯二甲酰，喹喔啉，α-酮酰胺和烯烃可以直接从醇类以中等到良好的产率形成。DIPEA =二异丙基乙胺。
• [EN] NOVEL IMIDAZOLIDINE COMPOUNDS AS ANDROGEN RECEPTOR MODULATORS<br/>[FR] NOUVEAUX COMPOSÉS D'IMIDAZOLIDINE EN TANT QUE MODULATEURS DU RÉCEPTEUR D'ANDROGÈNE
  申请人：GALAPAGOS NV

  公开号：WO2010029119A1

  公开（公告）日：2010-03-18

  Novel compounds are disclosed that have a Formula represented by the following: wherein X, R1, R2a, R2b, R2c, R3a R3b, R4a, R4b, R4c, and ml are as described herein. The compounds may be prepared as pharmaceutical compositions, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non- limiting example, cachexia, osteoporosis, sarcopenia, a decline in libido and/or sexual dysfunction.

  揭示了具有以下公式表示的新化合物：其中X、R1、R2a、R2b、R2c、R3a、R3b、R4a、R4b、R4c和ml如本文所述。这些化合物可以制备为药物组合物，并可用于预防和治疗包括人类在内的哺乳动物的各种疾病，例如消瘦、骨质疏松症、肌肉减少、性欲下降和/或性功能障碍。
• Thiazolidinedione derivatives
  申请人：BEECHAM GROUP PLC

  公开号：EP0299620A1

  公开（公告）日：1989-01-18

  A compound of formula (I): or a pharmaceutically acceptable salt thereof, wherein: A° represents nitrogen or a moiety wherein R1 represents hydrogen, alkyl or a substituted or unsubstituted aryl group; R2 represents a moiety R3-Y-Z- wherein R3 represents substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl or a substituted or unsubstituted oxazolyl group, and Y represents -(CH2)n. wherein n represents zero or any integer in the range of 1 to 6 and Z represents -CH2-,-CH(OH)- or -CO-; Ra and Rb each represent hydrogen or Ra and Rb together represent a bond; A represents a residue of a benzene ring, the carbon atoms of the residue having in total up to four substituents; and X represents 0 or S; a process for preparing such a compound, a pharmaceutical composition containing such a compound and the use of the compound and composition in medicine.

  一种化合物的化学式（I）： 或其药学上可接受的盐，其中：A°代表氮或一个基团 其中 R1代表氢、烷基或一个取代或未取代的芳基； R2代表一个基团R3-Y-Z-，其中R3代表取代或未取代的苯基、取代或未取代的吡啶基或一个取代或未取代的噁唑基，Y代表-(CH2)n，其中n代表零或在1到6范围内的任意整数，Z代表-CH2-，-CH(OH)-或-CO-； Ra和Rb各自代表氢或Ra和Rb一起代表一个键； A代表苯环的残基，残基的碳原子总共最多有四个取代基； X代表0或S；一种制备这种化合物的方法，含有这种化合物的药物组合物以及在医学中使用该化合物和组合物。
• Survivin inhibitors
  申请人：Wendt D. Michael

  公开号：US20070072833A1

  公开（公告）日：2007-03-29

  Compounds that inhibit survivin, compositions containing the compounds and methods of treating diseases in which survivin is unregulated or overexpressed are disclosed.

  抑制survivin的化合物、含有这些化合物的组合物以及治疗survivin失调或过度表达疾病的方法被揭示。
• N-sulfamoyl-N'-benzopyranpiperidine compounds and uses thereof
  申请人：Antel Jochen

  公开号：US20070117823A1

  公开（公告）日：2007-05-24

  N-sulfamoyl-N′-benzopyranpiperidine compounds of formula I and their physiologically acceptable acid addition salts, pharmaceutical compositions comprising them, processes for their preparation, and their use for the treatment and/or inhibition of glaucoma, epilepsy, bipolar disorders, migraine, neuropathic pain, obesity, type II diabetes, metabolic syndrome, alcohol dependence, and/or cancer, and related concomitant and/or secondary diseases or conditions.

  式I的N-磺胺基-N'-苯并吡啶啉化合物及其生理上可接受的酸盐，包含它们的药物组合物，其制备方法，以及它们用于治疗和/或抑制青光眼、癫痫、双相情感障碍、偏头痛、神经痛、肥胖症、2型糖尿病、代谢综合征、酒精依赖症和/或癌症的用途，以及相关的并发和/或继发疾病或症状。