N-[2-(4-Chlorophenyl)-1-methyl-2-oxoethyl]acetamide | 31952-51-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[2-(4-Chlorophenyl)-1-methyl-2-oxoethyl]acetamide
• 英文别名: 2-N-acetylamino-1-(4-chlorophenyl)-1-propanone；α-Acetamino-p-chlorpropiophenon；N-[2-(4-Chlor-phenyl)-1-methyl-2-oxo-aethyl]-acetamid；(+/-)-2-Acetylamino-1-(4-chlor-phenyl)-propan-1-on；N-[1-(4-chlorophenyl)-1-oxopropan-2-yl]acetamide
• CAS: 31952-51-9
• 化学式: C₁₁H₁₂ClNO₂
• 分子量: 225.675
• InChiKey: RZESBOUBFISYHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[2-(4-Chlorophenyl)-1-methyl-2-oxoethyl]acetamide 在 盐酸 、 三氟化硼乙醚 、 magnesium 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 123.5h， 生成 trans-5-(4-Chlorophenyl)-4,5-dimethyl-2-oxothiazolidine-3-carboxylic acid cyclohexylamide
  参考文献：
  名称：

  Preparation of Novel Hexythiazox Analogues

  摘要：

  Novel analogues of the title compound were prepared in several steps: via addition of methylmagnesium iodide to an acetamide derivative to yield diastereomeric amino alcohols, followed by hydrolysis, cyclization to the corresponding oxazole or thiazole derivative, and a coupling reaction with isocyanates. Results from acaricidal tests showed the compounds to be 100 times less active than hexythiazox.

  DOI：

  10.1002/(sici)1096-9063(199701)49:1<85::aid-ps486>3.0.co;2-z
• 作为产物：
  描述：

  2-Azido-1-(4-chloro-phenyl)-propan-1-one 在 盐酸 、 sodium carbonate 、 亚磷酸三乙酯 作用下， 以 水 、 甲苯 为溶剂， 生成 N-[2-(4-Chlorophenyl)-1-methyl-2-oxoethyl]acetamide
  参考文献：
  名称：

  N.C.A.18F-labelled norephedrine derivatives via α-aminopropiophenones

  摘要：

  N-protected 2-anlino-1-([F-18]fluorophenyl)-1-propanones are interesting fluorine-18 labelled intermediates to synthesize potential PET-tracers for mapping the adrenergic nervous system of the heart. Several N-protected alpha -aminoalkylarylketones were prepared to examine the direct nucleophilic n.c.a. F-18-fluorination of these carbonyl activated precursors. The influence of different protecting groups, the kind of leaving group and the stereoselective reduction of the keto function have been investigated in order to optimize the radiotracer production. It was shown that the F-18-substitution of the para-trimethylammonium group, e.g. of N-dibenzylated propiophenone, leads to radiochemical yields of up to 60%. The stereoselective reduction of the carbonyl function with formation of the n.c.a. erythro 2-N,N-dibenzylamino-1-(4-[F-18]fluorophenyl)-1-propanol was performed using BH3. THF. The diastereomeric excess was about 80%. Hydrogenolytical debenzylation was achieved with ammonium formiate in presence of palladium on charcoal to give the 4-[F-18]fluoronorephedrine with a radiochemical yield of 15-20% within a total time of 60 min.

  DOI：

  10.1002/1099-1344(200012)43:14<1345::aid-jlcr424>3.0.co;2-n

文献信息

• New Synthetic Strategy for High-Enantiopurity N-Protected α-Amino Ketones and their Derivatives by Asymmetric Hydrogenation
  作者：Tian Sun、Guohua Hou、Miaofeng Ma、Xumu Zhang

  DOI：10.1002/adsc.201000680

  日期：2011.2.11

  Asymmetric hydrogenation of α-dehydroamino ketones catalyzed by a rhodium-chiral phosphorus ligand complex (up to 99% ee, 1000 TON), represents an efficient approach to chiral α-amino ketones. The reduction of α-amino ketones catalyzed by palladium on carbon (Pd/C) leads to amphetamine precursors with quantitative yield and no significant enantioselectivity loss.

  铑-手性磷配体络合物（高达99％ee，1000 TON）催化的α-脱氢氨基酮的不对称氢化代表了一种有效的手性α-氨基酮的方法。钯/碳（Pd / C）催化的α-氨基酮的还原导致苯丙胺前体具有定量收率，并且没有明显的对映选择性损失。
• Reactions of amines. XVII. Oxidation of .alpha.-substituted .alpha.-amino ketones with lead tetraacetate
  作者：Henry E. Baumgarten、Donald F. McLaen、Harvey W. Taylor

  DOI：10.1021/jo00823a002

  日期：1971.12