N-methoxy-N-methyl-2-oxo-2-phenylacetamide | 141694-25-9

• 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: N-methoxy-N-methyl-2-oxo-2-phenylacetamide
• 英文别名: N-Methoxy-N-methyl-α-oxobenzeneacetamide
• CAS: 141694-25-9
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: DVHCLHHZEGEXKE-UHFFFAOYSA-N

物化性质

• 熔点：
  67 °C
• 沸点：
  271.6±23.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-methoxy-N-methyl-2-oxo-2-phenylacetamide 在 [RuCl2(benzene)]2 、 cerium(III) chloride heptahydrate 、 (S)-SunPhos 、 氢气 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以75%的产率得到(S)-2-hydroxy-N-methoxy-N-methyl-2-phenylacetamide
  参考文献：
  名称：

  Ru-catalyzed highly enantioselective hydrogenation of α-keto Weinreb amides

  摘要：

  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。

  DOI：

  10.1007/s11426-012-4790-8
• 作为产物：
  描述：

  二甲羟胺盐酸盐 、 苯甲酰甲酸 在 N-甲基吗啉 、 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以99%的产率得到N-methoxy-N-methyl-2-oxo-2-phenylacetamide
  参考文献：
  名称：

  Preparation of Weinreb Amides Using 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Chloride (DMT-MM)

  摘要：

  使用溶剂甲醇、异丙醇和乙腈（这些溶剂能够溶解4-(4,6-二甲氧基-1,3,5-三嗪-2-基)-4-甲基吗啉氯化物（DMT-MM）），从相应的羧酸成功制备了Weinreb酰胺。通过简单地将各种羧酸与DMT-MM和N,O-二甲基羟胺盐酸盐混合，它们被高效地转化为相应的Weinreb酰胺。

  DOI：

  10.1248/cpb.52.470

文献信息

• Preparation of Weinreb Amides Using 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium Chloride (DMT-MM)
  作者：Kazuhito Hioki、Hiroko Kobayashi、Rumi Ohkihara、Shohei Tani、Munetaka Kunishima

  DOI：10.1248/cpb.52.470

  日期：——

  Weinreb amides were successfully prepared from the corresponding carboxylic acids using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) in the solvents, methanol, isopropyl alcohol, and acetonitrile, which can solubilize DMT-MM. A variety of carboxylic acids were converted to the corresponding Weinreb amides in excellent yields by simply mixing with DMT-MM and N,O-dimethylhydroxylamine hydrochloride.

  使用溶剂甲醇、异丙醇和乙腈（这些溶剂能够溶解4-(4,6-二甲氧基-1,3,5-三嗪-2-基)-4-甲基吗啉氯化物（DMT-MM）），从相应的羧酸成功制备了Weinreb酰胺。通过简单地将各种羧酸与DMT-MM和N,O-二甲基羟胺盐酸盐混合，它们被高效地转化为相应的Weinreb酰胺。
• A Convenient Synthesis of N-Methoxy-N-Methylamides from Carboxylic Acids
  作者：Mukund P. Sibi、Chad C. Stessman、Jeffrey A. Schultz、James W. Christensen、Jianliang Lu、Mali Marvin

  DOI：10.1080/00397919508012689

  日期：1995.4

  Abstract Carboxylic acids can be converted to their corresponding N-methoxy-N-methylamides in high yields using 2-chloro-1-methylpyridinium iodide as the coupling agent. The reaction proceeds without racemization when chiral carboxylic acids are used as the starting material.

  摘要 使用 2-氯-1-甲基碘化吡啶鎓作为偶联剂，羧酸可以高产率转化为其相应的 N-甲氧基-N-甲基酰胺。当手性羧酸用作起始材料时，反应在没有外消旋化的情况下进行。
• Synthesis of Tridentate Chiral Spiro Aminophosphine−Oxazoline Ligands and Application to Asymmetric Hydrogenation of α‐Keto Amides
  作者：Feng‐Hua Zhang、Chen Wang、Jian‐Hua Xie、Qi‐Lin Zhou

  DOI：10.1002/adsc.201900251

  日期：2019.6.18

  A new type of tridentate chiral spiro aminophosphine−oxazoline ligands (SpiroOAP) have been synthesized through four steps. The SpiroOAP ligands are highly efficient for the asymmetric hydrogenation of α‐keto amides, providing a variety of synthetically useful α‐hydroxy amides with excellent enantioselectivity (up to 98% ee) and turnover numbers (up to 10,000).

  通过四个步骤合成了一种新型的三齿手性螺氨基氨基膦-恶唑啉配体（SpiroOAP）。SpiroOAP配体对于α-酮酰胺的不对称加氢非常有效，可提供多种合成有用的α-羟基酰胺，具有出色的对映选择性（最高98％ee）和周转率（最高10,000）。
• Rh(I)-Catalyzed Intermolecular Hydroacylation: Enantioselective Cross-Coupling of Aldehydes and Ketoamides
  作者：Kevin G. M. Kou、Diane N. Le、Vy M. Dong

  DOI：10.1021/ja504296x

  日期：2014.7.2

  Under Rh(I) catalysis, alpha-ketoamides undergo intermolecular hydroacylation with aliphatic aldehydes. A newly designed Josiphos ligand enables access to alpha-acyloxyamides with high atom-economy and enantioselectivity. On the basis of mechanistic and kinetic studies, we propose a pathway in which rhodium plays a dual role in activating the aldehyde for cross-coupling. A stereochemical model is provided to rationalize the sense of enantioinduction observed.
• .alpha.-Keto Amides and 1,2-Diketones from N,N'-Dimethoxy-N,N'-dimethylethanediamide. A Synthetic and Mechanistic Investigation
  作者：Mukund P. Sibi、Mali Marvin、Rajiv Sharma

  DOI：10.1021/jo00121a021

  日期：1995.8

  N,N'-Dimethoxy-N,N'-dimethylethanediamide (1), a 1,2-dicarbonyl synthon prepared from oxalyl chloride, undergoes nucleophilic displacements with Grignard reagents to provide alpha-keto amides 2-12 in 28-90% yields. The synthon also undergoes double nucleophilic displacements with organolithium reagents to furnish symmetrical 1,2-diketones 15-23 in 15-84% yields. A mechanism accounting for all the products from the reaction of 1 with nucleophiles has been proposed. Several control experiments were carried out to support the proposed mechanism.