13C-1-(4-chloro)acetophenone | 196212-78-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 13C-1-(4-chloro)acetophenone
• CAS: 196212-78-9
• 化学式: C₈H₇ClO
• 分子量: 155.585
• InChiKey: BUZYGTVTZYSBCU-PTQBSOBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.54
• 重原子数：
  10.0
• 可旋转键数：
  1.0
• 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：

  13C-1-(4-chloro)acetophenone 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以94%的产率得到13C-1-(4-chlorophenyl)ethanol
  参考文献：
  名称：

  Electrophilic amination of catecholboronate esters formed in the asymmetric hydroboration of vinylarenes

  摘要：

  (S)-(4-Methoxyphenyl)-ethyl-1,3,2-benzodioxaborole, (S)-1-(4-chlorophenyl)ethyl-1,3,2-benzodioxaborole and (S)-1-indanyl-1,3,2-benzodioxaborole. intermediates in the catalytic asymmetric hydroboration of 4-chloro-and 4-methoxystyrene, were isolated as pure oils in 75%, 84% and 49% yield respectively. For the first example, amination with N-chloromagnesio-N-methyl-O-trimethylsilhydroxylamine gave a mixture of (S)-1-(4-methoxyphenyl)-N-methylethylamine in 33% yield, 88% e.e. and (S)-1-(4-methoxyphenyl) ethanol in 31% yield, 86% e.e.. Related results were obtained in the other cases, and the steps of catalytic hydroboration and amination could be combined in a single sequence without isolation of the intermediate. Numerous variants were carried out in the amination procedure with only marginal improvements in chemoselectivity. An investigation of the mechanism was carried out using low temperature heteronuclear NMR on C-13-1-(S)-1-(4-chlorophenyl)ethyl-1,3,2-benzodioxaborole. The dual pathway is a result of an irreversible and unselective initial step. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00722-9
• 作为产物：
  描述：

  乙酰氯-1-13C 、 氯苯 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以40%的产率得到13C-1-(4-chloro)acetophenone
  参考文献：
  名称：

  Electrophilic amination of catecholboronate esters formed in the asymmetric hydroboration of vinylarenes

  摘要：

  (S)-(4-Methoxyphenyl)-ethyl-1,3,2-benzodioxaborole, (S)-1-(4-chlorophenyl)ethyl-1,3,2-benzodioxaborole and (S)-1-indanyl-1,3,2-benzodioxaborole. intermediates in the catalytic asymmetric hydroboration of 4-chloro-and 4-methoxystyrene, were isolated as pure oils in 75%, 84% and 49% yield respectively. For the first example, amination with N-chloromagnesio-N-methyl-O-trimethylsilhydroxylamine gave a mixture of (S)-1-(4-methoxyphenyl)-N-methylethylamine in 33% yield, 88% e.e. and (S)-1-(4-methoxyphenyl) ethanol in 31% yield, 86% e.e.. Related results were obtained in the other cases, and the steps of catalytic hydroboration and amination could be combined in a single sequence without isolation of the intermediate. Numerous variants were carried out in the amination procedure with only marginal improvements in chemoselectivity. An investigation of the mechanism was carried out using low temperature heteronuclear NMR on C-13-1-(S)-1-(4-chlorophenyl)ethyl-1,3,2-benzodioxaborole. The dual pathway is a result of an irreversible and unselective initial step. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00722-9