2,2-dimethyl-3-phenylpropionohydroxamic acid | 443682-78-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,2-dimethyl-3-phenylpropionohydroxamic acid
• 英文别名: N-hydroxy-2,2-dimethyl-3-phenylpropanamide
• CAS: 443682-78-8
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: GXBICLCEADVXME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-二乙氧基丙烷 、 2,2-dimethyl-3-phenylpropionohydroxamic acid 在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以91%的产率得到5,5-dimethyl-3-(1,1-dimethyl-2-phenylethyl)-1,4,2-dioxazole
  参考文献：
  名称：

  5,5-Dimethyl-1,4,2-dioxazoles as Versatile Aprotic Hydroxamic Acid Protecting Groups

  摘要：

  5,5-Dimethyl-1,4,2-dioxazoles are readily installed by transketalization of 2,2-diethoxypropane, where both the NH and OH moieties are protected in a nonprotic form. The dioxazoles are stable to a wide variety of reaction conditions and readily revert back to the hydroxamic acid by treatment with Nafion-H in 2-propanol. The method is applicable to primary, secondary, tertiary, and aromatic hydroxamic acids, and the acidity of the protons adjacent to the dioxazole allows alpha-functionalization.

  DOI：

  10.1021/jo0256890
• 作为产物：
  描述：

  2,2-二甲基-3-苯丙酸 在 草酰氯 、 盐酸羟胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以47%的产率得到2,2-dimethyl-3-phenylpropionohydroxamic acid
  参考文献：
  名称：

  5,5-Dimethyl-1,4,2-dioxazoles as Versatile Aprotic Hydroxamic Acid Protecting Groups

  摘要：

  5,5-Dimethyl-1,4,2-dioxazoles are readily installed by transketalization of 2,2-diethoxypropane, where both the NH and OH moieties are protected in a nonprotic form. The dioxazoles are stable to a wide variety of reaction conditions and readily revert back to the hydroxamic acid by treatment with Nafion-H in 2-propanol. The method is applicable to primary, secondary, tertiary, and aromatic hydroxamic acids, and the acidity of the protons adjacent to the dioxazole allows alpha-functionalization.

  DOI：

  10.1021/jo0256890

文献信息

• 5,5-Dimethyl-1,4,2-dioxazoles as Versatile Aprotic Hydroxamic Acid Protecting Groups
  作者：Michel Couturier、John L. Tucker、Caroline Proulx、Ghislain Boucher、Pascal Dubé、Brian M. Andresen、Arun Ghosh

  DOI：10.1021/jo0256890

  日期：2002.7.1

  5,5-Dimethyl-1,4,2-dioxazoles are readily installed by transketalization of 2,2-diethoxypropane, where both the NH and OH moieties are protected in a nonprotic form. The dioxazoles are stable to a wide variety of reaction conditions and readily revert back to the hydroxamic acid by treatment with Nafion-H in 2-propanol. The method is applicable to primary, secondary, tertiary, and aromatic hydroxamic acids, and the acidity of the protons adjacent to the dioxazole allows alpha-functionalization.