[(1S,2R)-2-(2-Bromo-5-hydroxy-phenyl)-2-hydroxy-1-methyl-ethyl]-carbamic acid tert-butyl ester | 198017-36-6

• 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: [(1S,2R)-2-(2-Bromo-5-hydroxy-phenyl)-2-hydroxy-1-methyl-ethyl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(1R,2S)-1-(2-bromo-5-hydroxyphenyl)-1-hydroxypropan-2-yl]carbamate
• CAS: 198017-36-6
• 化学式: C₁₄H₂₀BrNO₄
• 分子量: 346.221
• InChiKey: DNXMNLPZXXUWSC-UFBFGSQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(1S,2R)-2-(2-Bromo-5-hydroxy-phenyl)-2-hydroxy-1-methyl-ethyl]-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 反应 0.17h， 以95%的产率得到3-((1R,2S)-2-Amino-1-hydroxy-propyl)-4-bromo-phenol
  参考文献：
  名称：

  Preparation of 4- and 6-[76Br] bromometaraminol, two potential radiotracers for the study of the myocardial norepinephrine neuronal reuptake system with PET

  摘要：

  Metaraminol is a norepinephrine analogue which is transported with high affinity by the uptake-1 mechanism of the sympathetic nerve terminal. Radiolabelled metaraminol and analogues are promising radiotracers to assess the integrity of the myocardial nerve system. The bromo analogues, 4- and 6-bromometaraminol, were synthesized from commercially available metaraminol bitartrate. Structural assignments were made by PD-NMR experiments. 4- and 6-[Br-76]Bromometaraminol were prepared from N-Boc-metaraminol using [Br-76]NH4Br and peracetic acid as the brominating agent. The total radiochemical yield based on starting [Br-76]NH4Br was 17% and 38%, non decay-corrected, for derivative 4-[Br-76]bromometaraminol and 6-[Br-76]bromometaraminol, respectively, in a synthesis time of 3.5 hours including the preparation of [Br-76]NH4Br. The specific radioactivity obtained for both radiotracers was 130 mCi/mu mol (4.8 GBq/mu mol). Tissue distribution studies were performed in rats and revealed a low cardiac uptake for both derivatives. These preliminary results suggest that neither 4- nor 6-[Br-76]bromometaraminol are suitable radiotracers to study the myocardial norepinephrine neuronal reuptake system with Positron Emission Tomography.

  DOI：

  10.1002/(sici)1099-1344(199710)39:10<803::aid-jlcr27>3.0.co;2-r
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 N-溴代丁二酰亚胺(NBS) 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 [(1S,2R)-2-(2-Bromo-5-hydroxy-phenyl)-2-hydroxy-1-methyl-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Preparation of 4- and 6-[76Br] bromometaraminol, two potential radiotracers for the study of the myocardial norepinephrine neuronal reuptake system with PET

  摘要：

  Metaraminol is a norepinephrine analogue which is transported with high affinity by the uptake-1 mechanism of the sympathetic nerve terminal. Radiolabelled metaraminol and analogues are promising radiotracers to assess the integrity of the myocardial nerve system. The bromo analogues, 4- and 6-bromometaraminol, were synthesized from commercially available metaraminol bitartrate. Structural assignments were made by PD-NMR experiments. 4- and 6-[Br-76]Bromometaraminol were prepared from N-Boc-metaraminol using [Br-76]NH4Br and peracetic acid as the brominating agent. The total radiochemical yield based on starting [Br-76]NH4Br was 17% and 38%, non decay-corrected, for derivative 4-[Br-76]bromometaraminol and 6-[Br-76]bromometaraminol, respectively, in a synthesis time of 3.5 hours including the preparation of [Br-76]NH4Br. The specific radioactivity obtained for both radiotracers was 130 mCi/mu mol (4.8 GBq/mu mol). Tissue distribution studies were performed in rats and revealed a low cardiac uptake for both derivatives. These preliminary results suggest that neither 4- nor 6-[Br-76]bromometaraminol are suitable radiotracers to study the myocardial norepinephrine neuronal reuptake system with Positron Emission Tomography.

  DOI：

  10.1002/(sici)1099-1344(199710)39:10<803::aid-jlcr27>3.0.co;2-r

文献信息

• Preparation of 4- and 6-[76Br] bromometaraminol, two potential radiotracers for the study of the myocardial norepinephrine neuronal reuptake system with PET
  作者：Oliver Langer、Frédéric Dollé、Christian Loc'h、Christer Halldin、Françoise Vaufrey、Christine Coulon、Christian Crouzel、Kjell Någren、Bernard Mazière

  DOI：10.1002/(sici)1099-1344(199710)39:10<803::aid-jlcr27>3.0.co;2-r

  日期：1997.10

  Metaraminol is a norepinephrine analogue which is transported with high affinity by the uptake-1 mechanism of the sympathetic nerve terminal. Radiolabelled metaraminol and analogues are promising radiotracers to assess the integrity of the myocardial nerve system. The bromo analogues, 4- and 6-bromometaraminol, were synthesized from commercially available metaraminol bitartrate. Structural assignments were made by PD-NMR experiments. 4- and 6-[Br-76]Bromometaraminol were prepared from N-Boc-metaraminol using [Br-76]NH4Br and peracetic acid as the brominating agent. The total radiochemical yield based on starting [Br-76]NH4Br was 17% and 38%, non decay-corrected, for derivative 4-[Br-76]bromometaraminol and 6-[Br-76]bromometaraminol, respectively, in a synthesis time of 3.5 hours including the preparation of [Br-76]NH4Br. The specific radioactivity obtained for both radiotracers was 130 mCi/mu mol (4.8 GBq/mu mol). Tissue distribution studies were performed in rats and revealed a low cardiac uptake for both derivatives. These preliminary results suggest that neither 4- nor 6-[Br-76]bromometaraminol are suitable radiotracers to study the myocardial norepinephrine neuronal reuptake system with Positron Emission Tomography.