1-fluoro-3-(2-nitro-1H-imidazol-1-yl)propan-2-one | 110786-31-7

• 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: 1-fluoro-3-(2-nitro-1H-imidazol-1-yl)propan-2-one
• 英文别名: 1-Fluoro-3-(2-nitroimidazol-1-yl)propan-2-one；1-fluoro-3-(2-nitroimidazol-1-yl)propan-2-one
• CAS: 110786-31-7
• 化学式: C₆H₆FN₃O₃
• 分子量: 187.13
• InChiKey: PQQHYGCCPKMOAD-UHFFFAOYSA-N

物化性质

• 沸点：
  398.3±48.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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Ⅰ 作用下， 以 异丙醇 为溶剂， 反应 24.0h， 以49 mg的产率得到(R)-1-fluoro-3-(2-nitro-1H-imidazol-1-yl)propan-2-ol
  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
• 作为产物：
  描述：

  2-硝基咪唑 、 1-氯-3-氟-2-丙醇 在 Jones reagent 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以60%的产率得到1-fluoro-3-(2-nitro-1H-imidazol-1-yl)propan-2-one
  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
• 作为试剂：
  描述：

  1-氯-3-(2-硝基-1H-咪唑-1-基)丙烷-2-酮 在 1-fluoro-3-(2-nitro-1H-imidazol-1-yl)propan-2-one 、 还原型辅酶Ⅰ 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

• 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.