(-)-Norphenylephrine | 1420-80-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (-)-Norphenylephrine
• 英文别名: (S)-norphenylephrine；Norphenylephedrin；(S)-2-amino-1-(3-hydroxy-phenyl)-ethanol；(S)-2-Amino-1-(3-hydroxy-phenyl)-aethanol；3-[(1S)-2-amino-1-hydroxyethyl]phenol
• CAS: 1420-80-0
• 化学式: C₈H₁₁NO₂
• 分子量: 153.181
• InChiKey: LRCXRAABFLIVAI-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  11
• 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：
  66.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-Norphenylephrine 、 [¹¹C]cyanogen bromide 在 borate buffer 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Radiolabeled Phenethylguanidines:  Novel Imaging Agents for Cardiac Sympathetic Neurons and Adrenergic Tumors

  摘要：

  The norepinephrine transporter (NET) substrates [I-123]-m-iodobenzylguanidine (MIBG) and [C-11]-m-hydroxyephedrine (HED) are used as markers of cardiac sympathetic neurons and adrenergic tumors (pheochromocytoma, neuroblastoma). However, their rapid NET transport rates limit their ability to provide accurate measurements of cardiac nerve density. [C-11]Phenethylguanidine ([C-11]1a) and 12 analogues ([C-11]1b-m) were synthesized and evaluated as radiotracers with improved kinetics for quantifying cardiac nerve density. In isolated rat hearts, neuronal uptake rates of [C-11]1a-m ranged from 0.24 to 1.96 mL min(-1) (g wet wt)(-1), and six compounds had extremely long neuronal retention times (clearance T-1/2 > 20 h) due to efficient vesicular storage. Positron emission tomography (PET) studies in nonhuman primates with [C-11]1e, N-[C-11]guanyl-m-octopamine, which has a slow NET transport rate, showed improved myocardial kinetics compared to HED. Compound [C-11]1c, [C-11]-p-hydroxyphenethylguanidine, which has a rapid NET transport rate, avidly accumulated into rat pheochromocytoma xenograft tumors in mice. These encouraging findings demonstrate that radiolabeled phenethylguanidines deserve further investigation as radiotracers of cardiac sympathetic innervation and adrenergic tumors.

  DOI：

  10.1021/jm061398y
• 作为产物：
  描述：

  去甲苯福林 生成 (-)-Norphenylephrine
  参考文献：
  名称：

  杂环化合物合成的研究。第DXXVII部分。†。1,2,3,4-四氢-1-苯基异喹啉的绝对构型

  摘要：

  1,2,3,4-四氢-1-苯基异喹啉在C 1位的绝对构型可以从游离碱或其甲硫酮的CD曲线推导出。此外，对（+）-2-氨基-1-（3-羟基苯基）乙醇（V）的绝对构型进行了修改，发现其在C 1-位具有R-构型。

  DOI：

  10.1002/jhet.5570100405

文献信息

• A New Copper(I)–Tetrahydrosalen-Catalyzed Asymmetric Henry Reaction and Its Extension to the Synthesis of (S)-Norphenylephrine
  作者：Yan Xiong、Fei Wang、Xiao Huang、Yuehong Wen、Xiaoming Feng

  DOI：10.1002/chem.200601262

  日期：2007.1.12

  A new chiral hydrogenated salen catalyst has been developed for the asymmetric Henry reaction which produces the expected products in moderate to high yields (up to 98 %) with excellent enantioselectivities (up to 96 % ee). A variety of aromatic, heteroaromatic, enal, and aliphatic aldehydes were found to be suitable substrates in the presence of hydrogenated salen 1 f (10 mol %), (CuOTf)(2)C(7)H(8)

  已开发出一种用于不对称亨利反应的新型手性氢化塞伦催化剂，该催化剂能以中等至高产率（高达98％）产生预期的产物，并具有出色的对映选择性（高达96％ee）。发现存在氢化的salen 1f（10 mol％），（CuOTf）（2）C（7）H（8）（5 mol％）的情况下，各种芳香族，杂芳香族，烯醛和脂肪族醛都是合适的底物）和4 A分子筛。该方法是耐空气的，并且容易使用容易获得的试剂进行操作，并且已经成功地扩展到以商业上可得的间羟基苯甲醛为原料，以67％的总产率合成（S）-去氧肾上腺素。根据实验研究和MM +计算，
• Enantiomers of adrenaline-type amino alcohols by Burkholderia cepacia lipase-catalyzed asymmetric acylation
  作者：Katri Lundell、Erja Katainen、Anu Kiviniemi、Liisa T. Kanerva

  DOI：10.1016/j.tetasy.2004.10.027

  日期：2004.11

  Burkholderia cepacia lipase-catalyzed acylation with butanoic anhydride was used for the preparation of pharmaceutically important norphenylephrine and octopamine enantiomers, all in 98% ee. Reactivity of the phenolic OH groups and easy racemization, especially in the case of octopamine, complicated optimization. For norphenylephrine, chemical N-acylation was fast and allowed the subsequent enzymatic benzylic acylation in situ. The preparation of the octopamine enantiomers became possible by using the N-Fmoc protected substrate and by the Candida antarctica lipase B-catalyzed deprotection of the OH groups before the N-deprotection was performed. (C) 2004 Elsevier Ltd. All rights reserved.
• D'Amico et al., Chimica e l'Industria (Milan, Italy), 1956, vol. 38, p. 93,98
  作者：D'Amico et al.

  DOI：——

  日期：——
• US4643849A
  申请人：——

  公开号：US4643849A

  公开（公告）日：1987-02-17
• US4923882A
  申请人：——

  公开号：US4923882A

  公开（公告）日：1990-05-08