N-methyl-2-hydroxy-2-(2-thienyl)ethanamide | 143217-41-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: N-methyl-2-hydroxy-2-(2-thienyl)ethanamide
• 英文别名: 2-hydroxy-N-methyl-2-thiophen-2-ylacetamide
• CAS: 143217-41-8
• 化学式: C₇H₉NO₂S
• 分子量: 171.22
• InChiKey: PZVIIAAGUTVYOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  77.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-噻吩乙酰氯 在 甲基磺酰氯 、 三乙胺 、 乙腈 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 5.0h， 生成 N-methyl-2-hydroxy-2-(2-thienyl)ethanamide
  参考文献：
  名称：

  Base-promoted reaction of O-sulfonylated hydroxamic acids with nucleophiles. A new method for the synthesis of .alpha.-substituted amides

  摘要：

  Treatment of a series of hydroxamic acids 2 with mesyl chloride in the presence of 2 equiv of triethylamine at 0-degrees-C gives 2-chloroamides 3 in good yields. Use of a single equivalent of triethylamine gives the (N-mesyl-oxy)amides 1, which are versatile synthetic intermediates as they can be readily converted to 2-bromoamides 4 with lithium bromide and triethylamine and to 2-hydroxyamides 5 with triethylamine in aqueous acetonitrile.

  DOI：

  10.1021/jo00047a024

文献信息

• Ru-catalyzed highly enantioselective hydrogenation of α-keto Weinreb amides
  作者：MengMeng Zhao、WanFang Li、Xin Ma、WeiZheng Fan、XiaoMing Tao、XiaoMing Li、XiaoMin Xie、ZhaoGuo Zhang

  DOI：10.1007/s11426-012-4790-8

  日期：2013.3

  Asymmetric hydrogenation of α-keto Weinreb amides has been realized with [Ru((S)-Sunphos)(benzene)Cl]Cl as the catalyst and CeCl3·7H2O as the additive. A series of enantiopure α-hydroxy Weinreb amides (up to 97% ee) have been obtained. Catalytic amount of CeCl3·7H2O is essential for the high reactivity and enantioselectivity and the ratio of CeCl3·7H2O to [Ru((S)-Sunphos)(benzene)Cl]Cl plays an important role in the hydrogenation reaction.

  α-酮维纳布酰胺的不对称氢化已利用[Ru((S)-Sunphos)(benzene)Cl]Cl作为催化剂，CeCl3·7H2O作为添加剂实现。获得了一系列对映体纯的α-羟基维纳布酰胺（最高可达97%的对映体过量）。催化量的CeCl3·7H2O对于高反应性和对映选择性至关重要，CeCl3·7H2O与[Ru((S)-Sunphos)(benzene)Cl]Cl的比例在氢化反应中也起着重要作用。
• US4503052A
  申请人：——

  公开号：US4503052A

  公开（公告）日：1985-03-05
• Base-promoted reaction of O-sulfonylated hydroxamic acids with nucleophiles. A new method for the synthesis of .alpha.-substituted amides
  作者：Robert V. Hoffman、Naresh K. Nayyar、Wenting Chen

  DOI：10.1021/jo00047a024

  日期：1992.10

  Treatment of a series of hydroxamic acids 2 with mesyl chloride in the presence of 2 equiv of triethylamine at 0-degrees-C gives 2-chloroamides 3 in good yields. Use of a single equivalent of triethylamine gives the (N-mesyl-oxy)amides 1, which are versatile synthetic intermediates as they can be readily converted to 2-bromoamides 4 with lithium bromide and triethylamine and to 2-hydroxyamides 5 with triethylamine in aqueous acetonitrile.