[9-13C]-N-benzyl-2-bromo-N-methoxyacetamide | 884845-73-2

• 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: [9-13C]-N-benzyl-2-bromo-N-methoxyacetamide
• CAS: 884845-73-2
• 化学式: C₁₀H₁₂BrNO₂
• 分子量: 259.104
• InChiKey: KNBTWZTTWYYXLP-DETAZLGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  [9-13C]-N-benzyl-2-bromo-N-methoxyacetamide 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 [9-13C]-(2E)-N-benzyl-N-methoxy-3-(2,6,6-trimethylcyclohex)-1-enyl acrylamide
  参考文献：
  名称：

  Syntheses of 13C2-labelled 11Z-retinals

  摘要：

  To enable solid-state NMR investigations of the rhodopsin chromophore and its photointermediates, a series of 11Z-retinal isotopomers have been synthesised containing pairs of adjacent C-13 labels at C9/C10, C10/C11 or C11/C12, respectively. The C9 labelled carbon atom was introduced through the Heck reaction of a C-13-labelled Weinreb acrylamide derivative, and the label at the C12 position derived from a C-13-containing ethoxy Bestmann-Ohira reagent. The C-13 labels at C10 and C11 were introduced through the reaction of beta-ionone with labelled triethyl phosphonoacetate. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.092
• 作为产物：
  描述：

  N-benzyl-N-methoxyamine 、 (1-13C)bromoacetyl bromide 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以2.39 g的产率得到[9-13C]-N-benzyl-2-bromo-N-methoxyacetamide
  参考文献：
  名称：

  Syntheses of 13C2-labelled 11Z-retinals

  摘要：

  To enable solid-state NMR investigations of the rhodopsin chromophore and its photointermediates, a series of 11Z-retinal isotopomers have been synthesised containing pairs of adjacent C-13 labels at C9/C10, C10/C11 or C11/C12, respectively. The C9 labelled carbon atom was introduced through the Heck reaction of a C-13-labelled Weinreb acrylamide derivative, and the label at the C12 position derived from a C-13-containing ethoxy Bestmann-Ohira reagent. The C-13 labels at C10 and C11 were introduced through the reaction of beta-ionone with labelled triethyl phosphonoacetate. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.092

文献信息

• Accurate Measurements of ¹³C−¹³C <i>J</i>-Couplings in the Rhodopsin Chromophore by Double-Quantum Solid-State NMR Spectroscopy
  作者：Wai Cheu Lai、Neville McLean、Axel Gansmüller、Michiel A. Verhoeven、Gian Carlo Antonioli、Marina Carravetta、Luminita Duma、Petra H. M. Bovee-Geurts、Ole G. Johannessen、Huub J. M. de Groot、Johan Lugtenburg、Lyndon Emsley、Steven P. Brown、Richard C. D. Brown、Willem J. DeGrip、Malcolm H. Levitt

  DOI：10.1021/ja0581604

  日期：2006.3.1

  A new double-quantum solid-state NMR pulse sequence is presented and used to measure one-bond 13C-13C J-couplings in a set of 13C2-labeled rhodopsin isotopomers. The measured J-couplings reveal a perturbation of the electronic structure at the terminus of the conjugated chain but show no evidence for protein-induced electronic perturbation near the C11-C12 isomerization site. This work establishes NMR methodology for measuring accurate 1JCC values in noncrystalline macromolecules and shows that the measured J-couplings may reveal local electronic perturbations of mechanistic significance.