[9-13C]-(2E)-N-benzyl-N-methoxy-3-(2,6,6-trimethylcyclohex)-1-enyl acrylamide | 884845-79-8

• 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: [9-13C]-(2E)-N-benzyl-N-methoxy-3-(2,6,6-trimethylcyclohex)-1-enyl acrylamide
• CAS: 884845-79-8
• 化学式: C₂₀H₂₇NO₂
• 分子量: 314.429
• InChiKey: KQNCEFFCGUIZBB-GLBYAXABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 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]-(2E)-N-benzyl-N-methoxy-3-(2,6,6-trimethylcyclohex)-1-enyl acrylamide 在 copper(l) iodide 、 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 四丁基氟化铵 、 sodium hydride 、 异丙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 生成 [9,10-13C2]-(2E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6,8-trien-4-yn-1-ol
  参考文献：
  名称：

  Accurate Measurements of ¹³C−¹³C J-Couplings in the Rhodopsin Chromophore by Double-Quantum Solid-State NMR Spectroscopy

  摘要：

  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.

  DOI：

  10.1021/ja0581604
• 作为产物：
  描述：

  N-benzyl-N-methoxyamine 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 [9-13C]-(2E)-N-benzyl-N-methoxy-3-(2,6,6-trimethylcyclohex)-1-enyl acrylamide
  参考文献：
  名称：

  Accurate Measurements of ¹³C−¹³C J-Couplings in the Rhodopsin Chromophore by Double-Quantum Solid-State NMR Spectroscopy

  摘要：

  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.

  DOI：

  10.1021/ja0581604

文献信息

• Syntheses of 13C2-labelled 11Z-retinals
  作者：Neville J. McLean、Axel Gansmuller、Maria Concistre、Lynda J. Brown、Malcom H. Levitt、Richard C.D. Brown

  DOI：10.1016/j.tet.2011.07.092

  日期：2011.10

  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.