2-(4-fluoro-3-hydroxyphenyl)ethylamine hydrobromide | 128495-64-7

• 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: 2-(4-fluoro-3-hydroxyphenyl)ethylamine hydrobromide
• 英文别名: 5-(2-Aminoethyl)-2-fluorophenol;hydrobromide
• CAS: 128495-64-7
• 化学式: BrH*C₈H₁₀FNO
• 分子量: 236.084
• InChiKey: KGMYIYHEYHLYLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.61
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-fluoro-3-hydroxyphenyl)ethylamine hydrobromide 在 盐酸 、 三乙胺 、 mercury dichloride 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 (4-fluoro-m-hydroxyphenethyl)guanidine
  参考文献：
  名称：

  Synthesis and bioevaluation of [18F]4-fluoro-m-hydroxyphenethylguanidine ([18F]4F-MHPG): A novel radiotracer for quantitative PET studies of cardiac sympathetic innervation

  摘要：

  A new cardiac sympathetic nerve imaging agent, [F-18]4-fluoro-m-hydroxyphenethylguanidine ([F-18]4F-MHPG), was synthesized and evaluated. The radiosynthetic intermediate [F-18]4-fluoro-m-tyramine ([F-18]4F-MTA) was prepared and then sequentially reacted with cyanogen bromide and NH4Br/NH4OH to afford [F-18]4F-MHPG. Initial bioevaluations of [F-18]4F-MHPG (biodistribution studies in rats and kinetic studies in the isolated rat heart) were similar to results previously reported for the carbon-11 labeled analog [C-11]4F-MHPG. The neuronal uptake rate of [F-18]4F-MHPG into the isolated rat heart was 0.68 ml/min/g wet and its retention time in sympathetic neurons was very long (T-1/2 > 13 h). A PET imaging study in a nonhuman primate with [F-18]4F-MHPG provided high quality images of the heart, with heart-to-blood ratios at 80-90 min after injection of 5-to-1. These initial kinetic and imaging studies of [F-18]4F-MHPG suggest that this radiotracer may allow for more accurate quantification of regional cardiac sympathetic nerve density than is currently possible with existing neuronal imaging agents. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.106
• 作为产物：
  描述：

  2-(4-氟-3-甲氧基苯基)乙胺 在 氢溴酸 作用下， 反应 3.0h， 以63%的产率得到2-(4-fluoro-3-hydroxyphenyl)ethylamine hydrobromide
  参考文献：
  名称：

  2-（4-氟-3-羟苯基）乙胺和N-取代衍生物的合成和多巴胺受体亲和力。

  摘要：

  从4-氟-3-羟基甲苯开始合成2-（4-氟-3-羟基苯基）乙胺（26）和一些N，N-二烷基衍生物（27-30）及其对多巴胺的体外结合亲和力（报道了DA）受体。胺26可以被认为是DA的分子修饰，其中对羟基被氟取代。通过置换[3H] SCH 23390（D-1选择性）和[3H]哌酮（D-2选择性），评估了新化合物26-30对D-1和D-2 DA受体亚型的亲和力。胺26对D-1和D-2结合位点的亲和力比DA低约2倍。氨基被乙基，正丙基和2-苯基乙基取代会降低对D-1结合位点的亲和力，但会大大增强D-2结合位点的有效性。N-乙基-（28）和Nn-丙基-N-（2-苯基乙基）-2-（4-氟-3-羟基苯基）乙胺（30）是该系列中最有效的成员，对D-具有高选择性2个结合位点。Nn-丙基-N-（2-苯基乙基）-2-（3-氟-4-羟基苯基）乙胺异构体（31）观察到类似的效果，其对D-2位点的选择性是对D-1位

  DOI：

  10.1021/jm00171a014

文献信息

• Synthesis and dopamine receptor affinities of 2-(4-fluoro-3-hydroxyphenyl)ethylamine and N-substituted derivatives
  作者：Francesco Claudi、Mario Cardellini、Gian Mario Cingolani、Alessandro Piergentili、Guidubaldo Peruzzi、Walter Balduini

  DOI：10.1021/jm00171a014

  日期：1990.9

  The synthesis of 2-(4-fluoro-3-hydroxyphenyl)ethylamine (26) and of some N,N-dialkyl derivatives (27-30) starting from 4-fluoro-3-hydroxytoluene and their in vitro binding affinities for dopamine (DA) receptor are reported. The amine 26 can be regarded as a molecular modification of DA in which the para hydroxyl group is replaced by fluorine. The new compounds 26-30 were evaluated for their affinity

  从4-氟-3-羟基甲苯开始合成2-（4-氟-3-羟基苯基）乙胺（26）和一些N，N-二烷基衍生物（27-30）及其对多巴胺的体外结合亲和力（报道了DA）受体。胺26可以被认为是DA的分子修饰，其中对羟基被氟取代。通过置换[3H] SCH 23390（D-1选择性）和[3H]哌酮（D-2选择性），评估了新化合物26-30对D-1和D-2 DA受体亚型的亲和力。胺26对D-1和D-2结合位点的亲和力比DA低约2倍。氨基被乙基，正丙基和2-苯基乙基取代会降低对D-1结合位点的亲和力，但会大大增强D-2结合位点的有效性。N-乙基-（28）和Nn-丙基-N-（2-苯基乙基）-2-（4-氟-3-羟基苯基）乙胺（30）是该系列中最有效的成员，对D-具有高选择性2个结合位点。Nn-丙基-N-（2-苯基乙基）-2-（3-氟-4-羟基苯基）乙胺异构体（31）观察到类似的效果，其对D-2位点的选择性是对D-1位
• Biomimetic Phosphate-Catalyzed Pictet–Spengler Reaction for the Synthesis of 1,1′-Disubstituted and Spiro-Tetrahydroisoquinoline Alkaloids
  作者：Jianxiong Zhao、Daniel Méndez-Sánchez、John M. Ward、Helen C. Hailes

  DOI：10.1021/acs.joc.9b00527

  日期：2019.6.21

  Tetrahydroisoquinoline (THIQ) alkaloids are an important group of compounds that exhibit a range of bioactivities. Here, a phosphate buffer-catalyzed Pictet-Spengler reaction (PSR) using unreactive ketone substrates is described. A variety of 1,1'-disubstituted and spiro-tetrahydroisoquinoline alkaloids were readily prepared in one-step and high yields, highlighting the general applicability of this

  四氢异喹啉（THIQ）生物碱是一组具有一系列生物活性的重要化合物。在此，描述了使用未反应的酮底物的磷酸盐缓冲剂催化的Pictet-Spengler反应（PSR）。容易地一步制备高产率的多种1,1'-二取代和螺-四氢异喹啉碱生物碱，突显了这种方法的普遍适用性。这项研究的重点是磷酸盐在水基PSR中的作用，并为新的THIQ提供了一种原子效率高且可持续的途径。
• CLAUDI, FRANCESCO;CARDELLINI, MARIO;CINGOLANI, GIAN MARIO;PIERGENTILI, AL+, J. MED. CHEM., 33,(1990) N, C. 2408-2412
  作者：CLAUDI, FRANCESCO、CARDELLINI, MARIO、CINGOLANI, GIAN MARIO、PIERGENTILI, AL+

  DOI：——

  日期：——
• Synthesis and bioevaluation of [18F]4-fluoro-m-hydroxyphenethylguanidine ([18F]4F-MHPG): A novel radiotracer for quantitative PET studies of cardiac sympathetic innervation
  作者：Keun Sam Jang、Yong-Woon Jung、Phillip S. Sherman、Carole A. Quesada、Guie Gu、David M. Raffel

  DOI：10.1016/j.bmcl.2013.01.106

  日期：2013.3

  A new cardiac sympathetic nerve imaging agent, [F-18]4-fluoro-m-hydroxyphenethylguanidine ([F-18]4F-MHPG), was synthesized and evaluated. The radiosynthetic intermediate [F-18]4-fluoro-m-tyramine ([F-18]4F-MTA) was prepared and then sequentially reacted with cyanogen bromide and NH4Br/NH4OH to afford [F-18]4F-MHPG. Initial bioevaluations of [F-18]4F-MHPG (biodistribution studies in rats and kinetic studies in the isolated rat heart) were similar to results previously reported for the carbon-11 labeled analog [C-11]4F-MHPG. The neuronal uptake rate of [F-18]4F-MHPG into the isolated rat heart was 0.68 ml/min/g wet and its retention time in sympathetic neurons was very long (T-1/2 > 13 h). A PET imaging study in a nonhuman primate with [F-18]4F-MHPG provided high quality images of the heart, with heart-to-blood ratios at 80-90 min after injection of 5-to-1. These initial kinetic and imaging studies of [F-18]4F-MHPG suggest that this radiotracer may allow for more accurate quantification of regional cardiac sympathetic nerve density than is currently possible with existing neuronal imaging agents. (C) 2013 Elsevier Ltd. All rights reserved.
• One-pot chemoenzymatic synthesis of trolline and tetrahydroisoquinoline analogues
  作者：Jianxiong Zhao、Benjamin R. Lichman、John M. Ward、Helen C. Hailes

  DOI：10.1039/c7cc08024g

  日期：——

  Chemoenzymatic reaction cascades can provide access to chiral compounds from low-cost starting materials in one pot. Here we describe one-pot asymmetric routes to tetrahydroisoquinoline alkaloids (THIAs) using the Pictet–Spenglerase norcoclaurine synthase (NCS) followed by a cyclisation, to give alkaloids with two new heterocyclic rings. These reactions operated with a high atom economy to generate

  化学酶促反应级联反应可在一锅中从低成本原料中获得手性化合物。在这里，我们描述了使用Pictet-Spenglerase降鸟嘌呤合酶（NCS）进行一锅法到四氢异喹啉生物碱（THIAs）的一锅不对称路线，然后进行环化反应，得到具有两个新杂环的生物碱。这些反应以高原子经济性进行操作，从而以高收率产生THIA。