(S)-1-(2-nitroimidazol-1-yl)-3-fluoropropan-2-ol | 1334144-96-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (S)-1-(2-nitroimidazol-1-yl)-3-fluoropropan-2-ol
• 英文别名: (2S)-1-fluoro-3-(2-nitroimidazol-1-yl)propan-2-ol
• CAS: 1334144-96-5
• 化学式: C₆H₈FN₃O₃
• 分子量: 189.146
• InChiKey: HIIJZYSUEJYLMX-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-fluoro-3-(2-nitro-1H-imidazol-1-yl)propan-2-one 在 三羟甲基氨基甲烷盐酸盐 、 还原型辅酶II(NADPH)四钠盐 、 magnesium chloride 作用下， 以 异丙醇 为溶剂， 反应 24.0h， 以99%的产率得到
  参考文献：
  名称：

  Biocatalyzed synthesis of both enantiopure fluoromisonidazole antipodes

  摘要：

  Fluoromisonidazole (FMISO or F-MISO) is a radiotracer for positron emission tomography when F-18-labeled and is administrated in its racemic form. Herein, a straightforward synthesis of both enantiopure antipodes is proposed through a one-pot two-step microwave protocol to obtain a fluorinated ketone precursor followed by bioreduction using alcohol dehydrogenases from Rhodococcus ruber (ADH-A) or Lactobacillus brevis (LBADH). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.013

文献信息

• Mechanistic Investigations of Cooperative Catalysis in the Enantioselective Fluorination of Epoxides
  作者：Julia A. Kalow、Abigail G. Doyle

  DOI：10.1021/ja207256s

  日期：2011.10.12

  studies of the (salen)Co- and amine-cocatalyzed enantioselective ring opening of epoxides by fluoride. The kinetics of the reaction, as determined by in situ (19)F NMR analysis, are characterized by apparent first-order dependence on (salen)Co. Substituent effects, nonlinear effects, and reactivity with a linked (salen)Co catalyst provide evidence for a rate-limiting, bimetallic ring-opening step. To account

  本报告描述了（salen）Co 和胺共催化的环氧化物对映选择性开环的机理研究。通过原位 (19)F NMR 分析确定的反应动力学特征在于对 (salen)Co 的明显一级依赖性。取代基效应、非线性效应和与连接的 (salen) Co 催化剂的反应性为限速双金属开环步骤提供了证据。为了解释这些不同的数据，我们提出了一种机制，其中活性亲核氟物质是形成静止状态二聚体的氟化钴。胺助催化剂与 (salen) Co 的轴向连接促进二聚体解离，并且是观察到的协同性的起源。在这些研究的基础上，我们表明在比率、周转次数、氟化物开环反应的底物范围可以通过使用连接的salen框架来实现。报道了将该催化剂系统应用于快速（5 分钟）氟化以生成已知 PET 示踪剂 F-MISO 的未标记类似物。
• Co(salen)-mediated enantioselective radiofluorination of epoxides. Radiosynthesis of enantiomerically enriched [18F]F-MISO via kinetic resolution
  作者：Evgeny Revunov、Fedor Zhuravlev

  DOI：10.1016/j.jfluchem.2013.09.006

  日期：2013.12

  The first example of transition metal mediated enantioselective radiofluorination of epoxides is reported. The procedure utilizes gaseous [F-18]HF in a combination with (-)tetramisole and (R,R)-Co(salen), giving the corresponding (S,S)-F-18-fluorohydrines in 78-93% radiochemical yield (RCY) and 20-46% enantioselectivities (ee). The use of this methodology allowed for a single step radiosynthesis of [F-18]F-MISO, which took 1.5 h and after solid phase-based purification delivered [F-18]F-MISO in 81%/45% analytical/preparative RCY and 55% ee. (C) 2013 Elsevier B.V. All rights reserved.
• US9550704B2
  申请人：——

  公开号：US9550704B2

  公开（公告）日：2017-01-24
• Biocatalyzed synthesis of both enantiopure fluoromisonidazole antipodes
  作者：Wioleta Borzęcka、Iván Lavandera、Vicente Gotor

  DOI：10.1016/j.tetlet.2013.07.013

  日期：2013.9

  Fluoromisonidazole (FMISO or F-MISO) is a radiotracer for positron emission tomography when F-18-labeled and is administrated in its racemic form. Herein, a straightforward synthesis of both enantiopure antipodes is proposed through a one-pot two-step microwave protocol to obtain a fluorinated ketone precursor followed by bioreduction using alcohol dehydrogenases from Rhodococcus ruber (ADH-A) or Lactobacillus brevis (LBADH). (C) 2013 Elsevier Ltd. All rights reserved.