(1R,2S)-2-(tert-butoxycarbonylamino)-1-(3-hydroxyphenyl)-1-propanol | 112113-57-2

• 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: (1R,2S)-2-(tert-butoxycarbonylamino)-1-(3-hydroxyphenyl)-1-propanol
• 英文别名: tert-butyl N-[(1R,2S)-1-hydroxy-1-(3-hydroxyphenyl)propan-2-yl]carbamate
• CAS: 112113-57-2
• 化学式: C₁₄H₂₁NO₄
• 分子量: 267.325
• InChiKey: FPHQSOHXOSHSDJ-CABZTGNLSA-N

物化性质

• 熔点：
  60-65 °C(lit.)
• 沸点：
  450.7±40.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)
• 闪点：
  195 °F

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 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

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-(tert-butoxycarbonylamino)-1-(3-hydroxyphenyl)-1-propanol 在 N-溴代丁二酰亚胺(NBS) 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.67h， 生成 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 、 间羟胺 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 以65%的产率得到(1R,2S)-2-(tert-butoxycarbonylamino)-1-(3-hydroxyphenyl)-1-propanol
  参考文献：
  名称：

  合成用于心脏肾上腺神经系统的高比放射性的4-和6- [18F]氟甲基戊胺基PET示踪剂。

  摘要：

  先前已发现氟18（t（1/2）109.8分钟）和碳11（t（1/2）20.4分钟）标记的去甲肾上腺素类似物可用于正电子发射断层扫描（PET）放射性配体以作图心脏的肾上腺神经末梢。间氨基（（1R，2S）-2-氨基-1-（3-羟基苯基）-1-丙醇）是去甲肾上腺素的代谢稳定结构类似物，对去甲肾上腺素转运蛋白和囊泡单胺转运蛋白具有高亲和力。本文介绍了高比放射性标记的新的正氨基发射正电子发射断层照相术卤代类似物的放射合成。首先，用氟18标记的4-氟甲基戊胺（4- [18F] FMR或（1R，2S）-2-氨基-1-（4- [18F]氟-3-羟基苯基）-1-丙醇）及其三个其他立体异构体是根据以下关键步骤制备的：（a）相应的无载体添加的标记的氟苯甲醛与硝基乙烷的缩合，以及（b）非对映体产物混合物的HPLC（C18和手性）拆分为四个单独的对映体。其次，相应的6-氟类似物，氟-18标记的6-氟甲基氨基（6- [18F]

  DOI：

  10.1016/s0968-0896(00)00286-8

文献信息

• Synthesis of high-specific-radioactivity 4- and 6-[18F]fluorometaraminol- PET tracers for the adrenergic nervous system of the heart
  作者：Oliver Langer、Frédéric Dollé、Héric Valette、Christer Halldin、Françoise Vaufrey、Chantal Fuseau、Christine Coulon、Michéle Ottaviani、Kjell Någren、Michel Bottlaender、Bernard Maziére、Christian Crouzel

  DOI：10.1016/s0968-0896(00)00286-8

  日期：2001.3

  enantiomers. Secondly, the corresponding 6-fluoro analogues, fluorine-18-labeled 6-fluorometaraminol (6-[18F]FMR or (1R,2S)-2-amino-1-(2-[18F]fluoro-5-hydroxyphenyl)-1-propanol) and its three other enantiomers, were prepared in an analogous way. Typically, 0.48-0.55 GBq of 4-[18F]FMR and 0.14-0.15 GBq of 6-[18F]FMR could be obtained after 120-160 min total synthesis time, with a specific radioactivity of

  先前已发现氟18（t（1/2）109.8分钟）和碳11（t（1/2）20.4分钟）标记的去甲肾上腺素类似物可用于正电子发射断层扫描（PET）放射性配体以作图心脏的肾上腺神经末梢。间氨基（（1R，2S）-2-氨基-1-（3-羟基苯基）-1-丙醇）是去甲肾上腺素的代谢稳定结构类似物，对去甲肾上腺素转运蛋白和囊泡单胺转运蛋白具有高亲和力。本文介绍了高比放射性标记的新的正氨基发射正电子发射断层照相术卤代类似物的放射合成。首先，用氟18标记的4-氟甲基戊胺（4- [18F] FMR或（1R，2S）-2-氨基-1-（4- [18F]氟-3-羟基苯基）-1-丙醇）及其三个其他立体异构体是根据以下关键步骤制备的：（a）相应的无载体添加的标记的氟苯甲醛与硝基乙烷的缩合，以及（b）非对映体产物混合物的HPLC（C18和手性）拆分为四个单独的对映体。其次，相应的6-氟类似物，氟-18标记的6-氟甲基氨基（6- [18F]
• 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.