α-acetoxy-3-cyanoacetophenone | 83112-49-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-acetoxy-3-cyanoacetophenone
• 英文别名: 2-(3-Cyanophenyl)-2-oxoethyl acetate；[2-(3-cyanophenyl)-2-oxoethyl] acetate
• CAS: 83112-49-6
• 化学式: C₁₁H₉NO₃
• 分子量: 203.197
• InChiKey: NPVALYIRROGTHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  α-acetoxy-3-cyanoacetophenone 在 sodium hydroxide 、 baker's yeast 、 氨 、 双氧水 、 蔗糖 作用下， 以 甲醇 、 水 为溶剂， 反应 9.75h， 生成 S-3-(1,2-dihydroxyethyl)benzamide
  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：

  间碘苯腈 、 乙酰氧基乙酰氯 在 异丙基氯化镁 、 zinc(II) chloride 、 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 以54%的产率得到α-acetoxy-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