1-(3-chlorophenyl)-2-methoxypropan-1-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-chlorophenyl)-2-methoxypropan-1-one
• 化学式: C₁₀H₁₁ClO₂
• 分子量: 198.649
• InChiKey: LZFQXEKXCSBZJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  甲醇 、 3'-氯丙酮苯 在 4-硝基苯磺酸 、 间氯过氧苯甲酸 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以60%的产率得到1-(3-chlorophenyl)-2-methoxypropan-1-one
  参考文献：
  名称：

  碘化钠催化直接α-烷氧基化酮与醇的通过α-碘酮中间体的氧化

  摘要：

  AbstractThe direct α‐alkoxylation of ketones with alcohols via a sodium iodide‐catalyzed oxidative cross‐coupling has been developed. This protocol enables a range of alkyl aryl ketones to cross‐couple with an array of alcohols in synthetically useful yields. The mechanistic studies provided solid evidence supporting that an α‐iodo ketone was a key reaction intermediate, being converted into an α‐alkoxylated ketone via further oxidation to a hypervalent iodine species rather than a common nucleophilic substitution, and was generated from the ketone starting material via a radical intermediate. These new mechanism insights should have an effect on the design of iodide‐catalyzed oxidative cross‐coupling reactions between nucleophiles.magnified image

  DOI：

  10.1002/adsc.201500006

文献信息

• Sodium Iodide-Catalyzed Direct α-Alkoxylation of Ketones with Alcohols<i>via</i>Oxidation of α-Iodo Ketone Intermediates
  作者：Cuiju Zhu、Yuanfei Zhang、Huaiqing Zhao、Shijun Huang、Min Zhang、Weiping Su

  DOI：10.1002/adsc.201500006

  日期：2015.2.9

  AbstractThe direct α‐alkoxylation of ketones with alcohols via a sodium iodide‐catalyzed oxidative cross‐coupling has been developed. This protocol enables a range of alkyl aryl ketones to cross‐couple with an array of alcohols in synthetically useful yields. The mechanistic studies provided solid evidence supporting that an α‐iodo ketone was a key reaction intermediate, being converted into an α‐alkoxylated ketone via further oxidation to a hypervalent iodine species rather than a common nucleophilic substitution, and was generated from the ketone starting material via a radical intermediate. These new mechanism insights should have an effect on the design of iodide‐catalyzed oxidative cross‐coupling reactions between nucleophiles.magnified image