1-(4-苄氧基-3-碘苯基)乙酮 | 157953-15-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(4-苄氧基-3-碘苯基)乙酮
• 英文名称: 1-(4-benzyloxy-3-iodophenyl)ethanone
• 英文别名: 1-(4-(Benzyloxy)-3-iodophenyl)ethanone；1-(3-iodo-4-phenylmethoxyphenyl)ethanone
• CAS: 157953-15-6
• 化学式: C₁₅H₁₃IO₂
• 分子量: 352.172
• InChiKey: FEFFWFVJWPIJAZ-UHFFFAOYSA-N

物化性质

• 熔点：
  126.0-127.3 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  446.9±40.0 °C(Predicted)
• 密度：
  1.546±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-苄氧基-3-碘苯基)乙酮 在 镍 sodium hydroxide 、 copper(l) iodide 、 氢气 、 potassium carbonate 、 对甲苯磺酸 、 三乙胺 、 三苯基膦 、 palladium dichloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 1.0h， 生成 1-(4-羟基-3-(3-甲基丁-2-烯基)苯基)乙酮
  参考文献：
  名称：

  Regioselective Prenylation of Phenols by Palladium Catalyst: Syntheses of Prenylphenols and Chromans

  摘要：

  The palladium-catalyzed coupling reaction of iodophenols (1) with 2-methyl-3-butyn-2-ol gave alkynylphenols (2). Catalytic hydrogenation of 2 over Raney nickel and the subsequent dehydration of the resultant alkylphenols (3) gave regioselectively the desired prenylphenols (4). Dehydration of alkylphenols (3f-h) gave chromans (7).

  DOI：

  10.3987/com-94-6744
• 作为产物：
  描述：

  4-苯甲氧基苯乙酮 在 碘 、 silver trifluoroacetate 作用下， 以 氯仿 为溶剂， 生成 1-(4-苄氧基-3-碘苯基)乙酮
  参考文献：
  名称：

  Regioselective Prenylation of Phenols by Palladium Catalyst: Syntheses of Prenylphenols and Chromans

  摘要：

  The palladium-catalyzed coupling reaction of iodophenols (1) with 2-methyl-3-butyn-2-ol gave alkynylphenols (2). Catalytic hydrogenation of 2 over Raney nickel and the subsequent dehydration of the resultant alkylphenols (3) gave regioselectively the desired prenylphenols (4). Dehydration of alkylphenols (3f-h) gave chromans (7).

  DOI：

  10.3987/com-94-6744

文献信息

• Synthesis of some 5-phenylisoxazole-3-carboxylic acid derivatives as potent xanthine oxidase inhibitors
  作者：Shaojie Wang、Jufang Yan、Jian Wang、Jiarun Chen、Tingjian Zhang、Yong Zhao、Mingxing Xue

  DOI：10.1016/j.ejmech.2010.02.013

  日期：2010.6

  A number of 5-phenylisoxazole-3-carboxylic acid derivatives (5a-e, 11a-e) were synthesized and analyzed for their ability to inhibit xanthine oxidase. Most of the compounds exhibited potency levels in the micromolar/submicromolar range. The presence of a cyano group at the 3-position of phenyl moiety turned out to be the preferred substitution pattern, as its transformation into the nitro group determined a general reduction of the inhibitory potency. A molecular modeling study on compound 11a was performed to gain an insight into its binding mode with xanthine oxidase, and to provide the basis for further structure-guided design of new non-purine xanthine oxidase inhibitors related with 5-phenylisoxazole-3-carboxylic acid scaffold.
• Regioselective Prenylation of Phenols by Palladium Catalyst: Syntheses of Prenylphenols and Chromans
  作者：Masao Tsukayama、Makoto Kikuchi、Yasuhiko Kawamura

  DOI：10.3987/com-94-6744

  日期：——

  The palladium-catalyzed coupling reaction of iodophenols (1) with 2-methyl-3-butyn-2-ol gave alkynylphenols (2). Catalytic hydrogenation of 2 over Raney nickel and the subsequent dehydration of the resultant alkylphenols (3) gave regioselectively the desired prenylphenols (4). Dehydration of alkylphenols (3f-h) gave chromans (7).