2,2-dichloro-N-(2-phenylethyl)acetamide | 39106-18-8

• 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-dichloro-N-(2-phenylethyl)acetamide
• 英文别名: dichloro-acetic acid phenethylamide；Dichlor-essigsaeure-phenaethylamid；Dichloressigsaeure-β-phenaethylamid；Dichloracetyl-β-phenaethylamin；2,2-dichloro-N-phenethylacetamide
• CAS: 39106-18-8
• 化学式: C₁₀H₁₁Cl₂NO
• mdl: MFCD00094493
• 分子量: 232.109
• InChiKey: NXDSITABWUNLCU-UHFFFAOYSA-N

物化性质

• 熔点：
  78-79 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• 沸点：
  383.0±42.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  2,2-dichloro-N-(2-phenylethyl)acetamide 在 硫酸 、 硝酸 作用下， 生成 dichloro-acetic acid-(2,4-dinitro-phenethylamide)
  参考文献：
  名称：

  Isshiki; Kuwada, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1952, vol. 72, p. 69,71

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2-dichloro-N-phenethyl-acetimidoyl chloride 生成 2,2-dichloro-N-(2-phenylethyl)acetamide
  参考文献：
  名称：

  v.Braun; Jostes; Muench, Justus Liebigs Annalen der Chemie, 1927, vol. 453, p. 146

  摘要：

  DOI：

文献信息

• Dichloromeldrum’s Acid (DiCMA): A Practical and Green Amine Dichloroacetylation Reagent
  作者：David M. Heard、Alastair J. J. Lennox

  DOI：10.1021/acs.orglett.1c00850

  日期：2021.5.7

  dichloroacetylation of anilines and alkyl amines to produce α,α-dichloroacetamides, which are important motifs for medicinal chemistry. Products are formed in good to excellent yields with reagent grade solvents, and, as the only byproducts are acetone and CO2, no column chromatography is required. Thus, this reagent is practical, efficient, and green for the dichloroacetylation of primary amines.

  引入二氯甲mel酸是一种稳定的，不挥发的试剂，用于苯胺和烷基胺的二氯乙酰化，以生产α，α-二氯乙酰胺，这是药物化学的重要主题。使用试剂级溶剂可形成高至极佳收率的产物，并且由于唯一的副产物是丙酮和CO 2，因此无需柱色谱法。因此，该试剂对于伯胺的二氯乙酰化是实用，有效和绿色的。
• Homologation of Isocyanates with Lithium Carbenoids: A Straightforward Access to α-Halomethyl- and α,α-Dihalomethylamides
  作者：Vittorio Pace、Laura Castoldi、Ashenafi Mamuye、Wolfgang Holzer

  DOI：10.1055/s-0034-1379209

  日期：——

  Treatment of widely available isocyanates with monohalolithium and dihalolithium carbenoids provides a valuable protocol for the one-pot preparation of -halo- and ,-dihaloacetamide derivatives. While monohalolithium carbenoids can be prepared by a smooth lithium-halogen exchange, the preparation of the corresponding dihalo compounds proved to be highly dependent on the base used to realize the deprotonation, with lithium 2,2,6,6-tetramethylpiperidine emerging as optimal. The clear advantages of the procedure are: (a) broad scope of isocyanates that can be employed; (b) preservation of the optical purity when chiral materials are used; (c) divergent access to different haloamides by simply selecting the homologating agents. We also report an application of Charette's imidoyl triflate activation of a secondary amide to the synthesis of an -chloro ketone and N-15 NMR data for selected compounds.
• Chloromycetin (Chloramphenicol¹). Related Compounds Having Alkyl Side Chain Variations
  作者：Mildred C. Rebstock、George W. Moersch、Allen C. Moore、J. M. Vandenbelt

  DOI：10.1021/ja01152a030

  日期：1951.8
• Potential Antivirals. I. Simple Analogs of Chloramphenicol (Chloromycetin)
  作者：Arthur P. Phillips

  DOI：10.1021/ja01143a524

  日期：1952.12
• Improved Methods for the Synthesis of N-Acyltetrahydroisoquinolines
  作者：A. P. Venkov、L. K. Lukanov

  DOI：10.1080/00397919208021138

  日期：1992.12

  One-pot procedures for the synthesis of N-acyltetrahydroisoquinolines have been developed from 2-phenylethylamines, acyl chlorides or carboxylic acids and aldehydes.