N-t-BOC-metaraminol

• 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: N-t-BOC-metaraminol
• 英文别名: tert-butyl N-[1-hydroxy-1-(3-hydroxyphenyl)propan-2-yl]carbamate
• 化学式: C₁₄H₂₁NO₄
• mdl: MFCD24390325
• 分子量: 267.325
• InChiKey: FPHQSOHXOSHSDJ-UHFFFAOYSA-N

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

反应信息

• 作为反应物：
  描述：

  N-t-BOC-metaraminol 在 乙酰基次氟酸酯 作用下， 以 乙醇 、 溶剂黄146 、 乙腈 为溶剂， 反应 0.17h， 生成 6-fluoro-N-t-BOC-metaraminol
  参考文献：
  名称：

  6-[18F]fluorometaraminol. A radiotracer for in vivo mapping of adrenergic nerves of the heart

  摘要：

  The false neurotransmitter metaraminol has been 18F labeled and evaluated as a possible heart imaging agent on the basis of its selective accumulation in adrenergic nerves. Reaction of 6-(acetoxymercurio)-N-t-BOC-metaraminol with acetyl hypofluorite followed by removal of the BOC group provides a regiospecific synthesis of 6-fluorometaraminol (4). Use of acetyl hypo[18F]fluorite gives [18F]-4 in 60 min in 20-42% radiochemical yield. Systemic blockade of the neuronal uptake-1 carrier with desmethylimipramine or systemic destruction of the adrenergic nerves with 6-hydroxydopamine lowers [18F]-4 accumulation greater than or equal to 85% in all four regions of the rat heart. These preliminary findings suggest that [18F]-4 could be used to assess neuronal damage in various heart diseases by positron emission tomography.

  DOI：

  10.1021/jm00397a016
• 作为产物：
  描述：

  碳酸二叔丁酯 、 间氨基杂质14 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以92%的产率得到N-t-BOC-metaraminol
  参考文献：
  名称：

  6-[18F]fluorometaraminol. A radiotracer for in vivo mapping of adrenergic nerves of the heart

  摘要：

  The false neurotransmitter metaraminol has been 18F labeled and evaluated as a possible heart imaging agent on the basis of its selective accumulation in adrenergic nerves. Reaction of 6-(acetoxymercurio)-N-t-BOC-metaraminol with acetyl hypofluorite followed by removal of the BOC group provides a regiospecific synthesis of 6-fluorometaraminol (4). Use of acetyl hypo[18F]fluorite gives [18F]-4 in 60 min in 20-42% radiochemical yield. Systemic blockade of the neuronal uptake-1 carrier with desmethylimipramine or systemic destruction of the adrenergic nerves with 6-hydroxydopamine lowers [18F]-4 accumulation greater than or equal to 85% in all four regions of the rat heart. These preliminary findings suggest that [18F]-4 could be used to assess neuronal damage in various heart diseases by positron emission tomography.

  DOI：

  10.1021/jm00397a016

文献信息

• NOVEL PROCESS AND INTERMEDIATES USEFUL IN THE PREPARATION OF SYMPATHOMIMETIC AMINES
  申请人：INTERx RESEARCH CORPORATION

  公开号：EP0036426B1

  公开（公告）日：1986-04-23
• US4338455A
  申请人：——

  公开号：US4338455A

  公开（公告）日：1982-07-06
• 6-[18F]fluorometaraminol. A radiotracer for in vivo mapping of adrenergic nerves of the heart
  作者：Suresh G. Mislankar、David L. Gildersleeve、Donald M. Wieland、Christopher C. Massin、G. Keith Mulholland、Steven A. Toorongian

  DOI：10.1021/jm00397a016

  日期：1988.2

  The false neurotransmitter metaraminol has been 18F labeled and evaluated as a possible heart imaging agent on the basis of its selective accumulation in adrenergic nerves. Reaction of 6-(acetoxymercurio)-N-t-BOC-metaraminol with acetyl hypofluorite followed by removal of the BOC group provides a regiospecific synthesis of 6-fluorometaraminol (4). Use of acetyl hypo[18F]fluorite gives [18F]-4 in 60 min in 20-42% radiochemical yield. Systemic blockade of the neuronal uptake-1 carrier with desmethylimipramine or systemic destruction of the adrenergic nerves with 6-hydroxydopamine lowers [18F]-4 accumulation greater than or equal to 85% in all four regions of the rat heart. These preliminary findings suggest that [18F]-4 could be used to assess neuronal damage in various heart diseases by positron emission tomography.