2-acetoxy-benzoic acid diethylamide | 91731-53-2

• 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-acetoxy-benzoic acid diethylamide
• 英文别名: 2-Acetoxy-benzoesaeure-diaethylamid；[2-(Diethylcarbamoyl)phenyl] acetate
• CAS: 91731-53-2
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: UUQSOMUVEYVOQB-UHFFFAOYSA-N

物化性质

• 沸点：
  374.8±25.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  2-acetoxy-benzoic acid diethylamide 在 水 作用下， 生成 N,N-二乙基水杨酰胺
  参考文献：
  名称：

  通过分子内的O-N酰基转移O-酰基水杨酰胺的重排：相邻羧酸基团的速率增强

  摘要：

  游离羧酸基团参与水杨酰胺二羧酸半酯的O-N酰基转移反应的速率提高。

  DOI：

  10.1002/jps.2600790724
• 作为产物：
  描述：

  乙酰氯 、 2-iodophenyl diethylcarbamate 在 苯基锂 作用下， 以85%的产率得到2-acetoxy-benzoic acid diethylamide
  参考文献：
  名称：

  亚毫秒有机合成：通过微流体快速混合超越 Fries 重排

  摘要：

  快速混合以超越重排化学依赖于反应伙伴之间的相遇。有时，合作伙伴之一会在等待期间改变形状，破坏了预期的结果。金等人。设计了一种微流体装置来防止这种拙劣的遭遇发生。该装置在低温下运行以防止单个反应物发生异构化。它还实现了快速流速，以在微秒时间尺度上最大化反应物之间的相遇。作者通过在其中一种试剂进行 Fries 重排之前实现双分子碳-碳偶联来展示该装置，该重排会将相邻基团转移到偶联位点。科学，这个问题 p。691 双分子偶联可以通过极快速的低温微流体混合来超越快速的单分子重排。在化学合成中，快速的分子内重排通常会挫败位点选择性双分子功能化的尝试。我们开发了一种微流体技术，它超越了非常快速的阴离子 Fries 重排，以化学选择性地将邻位的碘苯基氨基甲酸酯官能化。该技术的核心是我们设计的芯片微反应器，即使在低温下也可以提供亚毫秒范围的反应时间。该微反应器用于合成具有驱虫活性的生物活性分子 afesa

  DOI：

  10.1126/science.aaf1389

文献信息

• 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.
• A Novel and Expeditious Reduction of Tertiary Amides to Aldehydes Using Cp₂Zr(H)Cl
  作者：Jonathan M. White、Ashok Rao Tunoori、Gunda I. Georg

  DOI：10.1021/ja002149g

  日期：2000.12.1

  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).
• Formation of domain structure of erythrocyte membrane in Wistar rat fed with CeCl3 per os
  作者：Yi Cheng、Maozi Liu、You Li、Rongchang Li、Chunli Bai、Kui Wang

  DOI：10.1007/bf02884943

  日期：2000.3

  To explore the possibility of absorption of lanthanides via digestive duct and their effects on the membrane structure and permeability of erythrocytes, the fine structure of erythrocyte membrane from Wistar rats, fed for 70 days of daily administration per os with 20 mg CeCl3/kg weight, was imaged by means of atomic force microscopy and FT-IR deconvolution spectra. The results show that, although the erythrocytes maintain the intact shape, the change of secondary structure, aggregation and crosslinking of the protein particles of membrane surface and the enlarged lipid regions lead to the domain structure formation. This structure might be responsible for the increasing permeability of erythrocyte membrane.
• Canonica et al., Annali di Chimica, 1955, vol. 45, p. 205,213
  作者：Canonica et al.

  DOI：——

  日期：——
• Rearrangement of O-Acylsalicylamides via Intramolecular O-to-N Transacylation: Rate Enhancement by an Adjacent Carboxylic Acid Group
  作者：F.A. Tawfig、L. Dittert、P.A. Crooks、A. Hussain

  DOI：10.1002/jps.2600790724

  日期：1990.7

  Involvement of the free carboxylic acid group in the rate enhancement of O-to-N transacylation reactions of dicarboxylic acid hemiesters of salicylamide.

  游离羧酸基团参与水杨酰胺二羧酸半酯的O-N酰基转移反应的速率提高。