[10,11-13C2]-1,3,3-trimethyl-2-((1E,3E)-3-methylhexa-1,3-dien-5-ynyl)cyclohex-1-ene | 1342310-22-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [10,11-13C2]-1,3,3-trimethyl-2-((1E,3E)-3-methylhexa-1,3-dien-5-ynyl)cyclohex-1-ene
• CAS: 1342310-22-8
• 化学式: C₁₆H₂₂
• 分子量: 216.329
• InChiKey: VZHBEOMOYZVQPM-OZEXRXBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  tert-butyl((3-iodobut-2-en-1-yl)oxy)dimethylsilane 、 [10,11-13C2]-1,3,3-trimethyl-2-((1E,3E)-3-methylhexa-1,3-dien-5-ynyl)cyclohex-1-ene 在 copper(l) iodide 、 四(三苯基膦)钯 、 异丙胺 作用下， 反应 3.5h， 生成 [10,11-13C2]-((2Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,6,8-trien-4-ynyloxy)(tert-butyl)dimethylsilane 、 [10,11-13C2]-((2E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,6,8-trien-4-ynyloxy)(tert-butyl)dimethylsilane
  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：

  在 四丙基高钌酸铵 、 N-甲基吗啉氧化物 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 1.25h， 生成 [10,11-13C2]-1,3,3-trimethyl-2-((1E,3E)-3-methylhexa-1,3-dien-5-ynyl)cyclohex-1-ene
  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