2-chloro-2-deuterio-1-phenyl-ethanone | 943148-97-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-chloro-2-deuterio-1-phenyl-ethanone
• 英文别名: α-Chlor-α-D-acetophenon；β-Deuterio-phenacylchlorid；Phenacylchlorid-d1
• CAS: 943148-97-8
• 化学式: C₈H₇ClO
• 分子量: 155.588
• InChiKey: IMACFCSSMIZSPP-RAMDWTOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  10.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-chloro-2-deuterio-1-phenyl-ethanone 在 chromium dichloride 作用下， 以 四氢呋喃 、 水 为溶剂， 以100%的产率得到acetophenone-d1
  参考文献：
  名称：

  A mechanistic study of the chromium(II)-mediated transformations of trichloromethyl alkyls and carbinols: evidence for carbene, carbyne, and carbenoid intermediates

  摘要：

  Using CrCl2 in THF at room temperature, trichloromethyl carbinols and trichloromethylalkanes are readily transformed to the highly reactive alpha-chlorocarbenes, carbynes and alpha-chloro-alpha-chromium(III) vinylidene carbenoids. A mechanistic study is carried out to determine the nature of the intermediates. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.150
• 作为产物：
  描述：

  苯甲醇-Alpha,Alpha-d2 在 chromium dichloride 、 pyridinium chlorochromate 、 三氯乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 2-chloro-2-deuterio-1-phenyl-ethanone
  参考文献：
  名称：

  A mechanistic study of the chromium(II)-mediated transformations of trichloromethyl alkyls and carbinols: evidence for carbene, carbyne, and carbenoid intermediates

  摘要：

  Using CrCl2 in THF at room temperature, trichloromethyl carbinols and trichloromethylalkanes are readily transformed to the highly reactive alpha-chlorocarbenes, carbynes and alpha-chloro-alpha-chromium(III) vinylidene carbenoids. A mechanistic study is carried out to determine the nature of the intermediates. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.150

文献信息

• Reactions of diazo ketones with activated unsaturated compounds in the presence of gallium trichloride
  作者：R. A. Novikov、Yu. V. Tomilov、O. M. Nefedov

  DOI：10.1007/s11172-014-0444-7

  日期：2014.2

  Diazoacetone reacts with methyl acrylate in the presence of anhydrous GaCl3 to give isomeric methyl 2-acetylcyclopropanecarboxylates rather than pyrazolines obtained from diazo esters or by noncatalytic reactions. In a similar reaction, diazoacetophenone yields methyl 2-benzoylcyclopropanecarboxylates, benzoylmethyl acrylate, and benzoylmethyl 2-benzoylcyclopropanecarboxylate via partial transesterification

  在无水 GaCl3 存在下，重氮丙酮与丙烯酸甲酯反应生成异构的 2-乙酰环丙烷羧酸甲酯，而不是从重氮酯或通过非催化反应获得的吡唑啉。在类似的反应中，重氮苯乙酮通过部分酯交换反应生成 2-苯甲酰环丙烷羧酸甲酯、丙烯酸苯甲酰甲酯和 2-苯甲酰环丙烷羧酸苯甲酰甲酯。在 CH2Cl2-HCl-H2O 系统中将等摩尔量的 GaCl3 添加到重氮丙酮中意外地产生 4,5-二甲基呋喃-3(2H)-one 和 1,1'-oxybis(propan-2-one)。
• Copper(I)-Promoted Synthesis of Chloromethyl Ketones from Trichloromethyl Carbinols
  作者：Ram N. Ram、T. P. Manoj

  DOI：10.1021/jo8007644

  日期：2008.7.1

  Reaction of several trichloromethyl carbinols with 2 equiv of CuCl/bpy in refluxing DCE for 3 h afforded chloromethyl ketones in excellent yield by 1,2-H shift in the copper-chlorocarbenoid intermediate.

  几种三氯甲基甲醇与2当量的CuCl / bpy在回流DCE中反应3小时，得到的氯甲基酮的收率很高，通过铜-氯类化合物中间体的1,2-H转移。
• Triazabicyclodecene:  An Effective Isotope Exchange Catalyst in CDCl₃
  作者：Cyrille Sabot、Kanduluru Ananda Kumar、Cyril Antheaume、Charles Mioskowski

  DOI：10.1021/jo070307h

  日期：2007.6.1

  We describe the first effective H/D exchange reaction with acidic substrates in CDCl3 at room temperature. The particularly mild reaction conditions involved (solvent, base, and temperature) allow the chemoselective deuteration of ketones over esters. An NMR study was conducted with the aim of rationalizing the results obtained in the presence of TBD as catalyst.