2-(4-chlorophenoxy)-N,N-diethylacetamide | 19039-69-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-chlorophenoxy)-N,N-diethylacetamide
• CAS: 19039-69-1
• 化学式: C₁₂H₁₆ClNO₂
• mdl: MFCD01121481
• 分子量: 241.718
• InChiKey: CKMXXQZVHLKTAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenoxy)-N,N-diethylacetamide 在 Schwartz's reagent 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以90%的产率得到p-chlorophenoxyacetaldehyde
  参考文献：
  名称：

  A Novel and Expeditious Reduction of Tertiary Amides to Aldehydes Using Cp₂Zr(H)Cl

  摘要：

  Functional group manipulations continue to play an important role in organic synthesis, and hence the development of new methods to carry out these transformations remains an important part of organic chemistry. The reduction of amides to aldehydes is one such transformation, and although several methods are available,(1) many are substrate specific,(2) the outcome of the reaction being dependent upon the nature of the nitrogen substituent. Problems with existing techniques, which generally require the use of highly reactive reagents such as aluminum and boron hydrides, include low functional group tolerance, over-reduction to amines or alcohols, or the formation of other byproducts. Herein, we report a general procedure for the conversion of tertiary amides to:aldehydes, which employs a commercially available reagent, Cp2Zr(H)Cl (Schwartz reagent(3)) and operates under mild conditions at room temperature (Scheme 1).

  DOI：

  10.1021/ja002149g

文献信息

• Amido compounds and their use as pharmaceuticals
  申请人：Yao Wenqing

  公开号：US20060122197A1

  公开（公告）日：2006-06-08

  The present invention relates to inhibitors of 11-β hydroxyl steroid dehydrogenase type 1, antagonists of the mineralocorticoid receptor (MR), and pharmaceutical compositions thereof. The compounds of the invention can be useful in the treatment of various diseases associated with expression or activity of 11-β hydroxyl steroid dehydrogenase type 1 and/or diseases associated with aldosterone excess.

  本发明涉及11-β羟基类固醇脱氢酶类型1的抑制剂、矿物质皮质激素受体（MR）的拮抗剂及其制药组合物。本发明的化合物可用于治疗与11-β羟基类固醇脱氢酶类型1的表达或活性有关的各种疾病和/或与醛固酮过多有关的疾病。
• Mild and Selective Hydrozirconation of Amides to Aldehydes Using Cp₂Zr(H)Cl:  Scope and Mechanistic Insight
  作者：Jared T. Spletstoser、Jonathan M. White、Ashok Rao Tunoori、Gunda I. Georg

  DOI：10.1021/ja066362+

  日期：2007.3.1

  An investigation of the use of Cp2Zr(H)Cl (Schwartz's reagent) to reduce a variety of amides to the corresponding aldehydes under very mild reaction conditions and in high yields is reported. A range of tertiary amides, including Weinreb's amides, can be converted directly to the corresponding aldehydes with remarkable chemoselectivity. Primary and secondary amides proved to be viable substrates for reduction as well, although the yields were somewhat diminished as compared to the corresponding tertiary amides. Results from NMR experiments suggested the presence of a stable, 18-electron zirconacycle intermediate that presumably affords the aldehyde upon water or silica gel workup. A series of competition experiments revealed a preference of the reagent for substrates in which the lone pair of the nitrogen is electron releasing and thus more delocalized across the amide bond by resonance. This trend accounts for the observed excellent selectivity for tertiary amides versus esters. Experiments regarding the solvent dependence of the reaction suggested a kinetic profile similar to that postulated for the hydrozirconation of alkenes and alkynes. Addition of p-anisidine to the reaction intermediate resulted in the formation of the corresponding imine mimicking the addition of water that forms the aldehyde.
• [EN] AMIDO COMPOUNDS AND THEIR USE AS PHARMACEUTICALS<br/>[FR] COMPOSES AMIDO ET LEUR UTILISATION COMME PRODUITS PHARMACEUTIQUES
  申请人：INCYTE CORP

  公开号：WO2006020598A3

  公开（公告）日：2007-01-04
• EP1778229A4
  申请人：——

  公开号：EP1778229A4

  公开（公告）日：2009-06-17
• AMIDO COMPOUNDS AND THEIR USE AS PHARMACEUTICALS
  申请人：INCYTE CORPORATION

  公开号：EP1778229A2

  公开（公告）日：2007-05-02