cis-4-fluoro-L-proline | 60828-35-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: cis-4-fluoro-L-proline
• 英文别名: 4-fluoro-L-proline；4-Fluoroproline；(2S)-4-fluoropyrrolidine-2-carboxylic acid
• CAS: 60828-35-5
• 化学式: C₅H₈FNO₂
• 分子量: 133.122
• InChiKey: ZIWHMENIDGOELV-BKLSDQPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cis-4-fluoro-L-proline 、 氢氧化钾 、 4-Chloro-2-fluoro-5-(1-methylethoxy)phenyl isothiocyanate 、 N,N'-二环己基碳二亚胺 在 resultant product 、 crude product 、 silica gel 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 19.0h， 以to give 3.24 g (85% yield) of the desired product的产率得到3-[[4-Chloro-2-fluoro-5-(1-methylethoxy)phenyl]imino]-6-fluorotetrahydro-1H,3H-pyrrolo [1,2-c]thiazol-1-one
  参考文献：
  名称：

  Oxa-and thia(di)azabicyclic compounds

  摘要：

  本发明涉及氧杂二氮杂双环和硫杂二氮杂双环化合物，一种制备它们的方法以及它们作为除草剂的应用。

  公开号：

  US05712225A1
• 作为产物：
  描述：

  三乙胺 、 硫酰氟 、 potassium carbonate 在 乙酸乙酯 作用下， 以 乙腈 为溶剂， 反应 20.33h， 以obtaining a crude product of 4-fluoroproline derivative的产率得到
  参考文献：
  名称：

  Process for production of fluoro derivative

  摘要：

  发现可以通过在有机碱或有机碱和“含有有机碱和氢氟酸盐或复合物”的情况下，将羟基衍生物与亚磺酰氟（SO2F2）反应来生产氟衍生物。根据目前的生产工艺，不需要使用不适合工业用途的全氟烷基磺酰氟，而且即使在大规模生产中，也可以优势地生产重要的药物、农药和光学材料的光学活性氟衍生物，特别是4-氟脯氨酸衍生物、2'-脱氧-2'-氟尿苷衍生物、光学活性α-氟羧酸酯衍生物等。

  公开号：

  US07807858B2

文献信息

• Dehydroxyfluorination Agent
  申请人：Ishii Akihiro

  公开号：US20090250658A1

  公开（公告）日：2009-10-08

  There is provided a novel, useful dehydroxyfluorination agent containing sulfuryl fluoride (SO 2 F 2 ) and an organic base that is free from a free hydroxyl group in the molecule. According to the present dehydroxyfluorination agent, it is not necessary to use perfluoroalkanesulfonyl fluoride, which is not preferable in large-scale use, and it is possible to advantageously produce optically-active fluoro derivatives, which are important intermediates of medicines, agricultural chemicals and optical materials, for example, 4-fluoroproline derivatives, 2′-deoxy-2′-fluorouridine derivatives, optically-active α-fluorocarboxylate derivatives, and monofluoromethyl derivatives, even in large scale.

  提供了一种新颖、有用的脱羟基氟化剂，其含有亚磺酰氟（SO2F2）和分子中不含有自由羟基的有机碱。根据这种脱羟基氟化剂，不需要使用不适合大规模使用的全氟烷基磺酰氟，并且即使在大规模生产中，也可以优势地生产出重要的药物、农药和光学材料的光学活性氟衍生物，例如4-氟脯氨酸衍生物、2'-脱氧-2'-氟尿苷衍生物、光学活性α-氟羧酸酯衍生物和单氟甲基衍生物。
• Process for Production of Fluoro Derivative
  申请人：Ishii Akihiro

  公开号：US20080125589A1

  公开（公告）日：2008-05-29

  It was found that a fluoro derivative can be produced by reacting a hydroxy derivative with sulfuryl fluoride (SO 2 F 2 ) in the presence of an organic base or in the presence of an organic base and “a salt or complex comprising an organic base and hydrogen fluoride”. According to the present production process, it is not necessary to use perfluoroalkanesulfonyl fluoride, which is not preferable in industrial use, and it is possible to advantageously produce optically-active fluoro derivatives, which are important intermediates of medicines, agricultural chemicals and optical materials, specifically 4-fluoroproline derivatives, 2′-deoxy-2′-fluorouridine derivatives, optically-active α-fluorocarboxylate derivatives, and the like, even in a large scale.

  研究发现，在有机碱的存在下或有机碱和“含有有机碱和氢氟酸的盐或复合物”的存在下，通过将羟基衍生物与亚磺酰氟（SO2F2）反应，可以生成氟衍生物。根据目前的生产工艺，不需要使用在工业上不理想的全氟烷基磺酰氟，而且可以优势地大规模生产重要的药物、农药和光学材料中间体，特别是4-氟脯氨酸衍生物、2'-去氧核糖-2'-氟尿苷衍生物、光学活性α-氟羧酸酯衍生物等光学活性氟衍生物。
• Process for production of fluoro derivative
  申请人：Central Glass Company, Limited

  公开号：US07807858B2

  公开（公告）日：2010-10-05

  It was found that a fluoro derivative can be produced by reacting a hydroxy derivative with sulfuryl fluoride (SO2F2) in the presence of an organic base or in the presence of an organic base and “a salt or complex comprising an organic base and hydrogen fluoride”. According to the present production process, it is not necessary to use perfluoroalkanesulfonyl fluoride, which is not preferable in industrial use, and it is possible to advantageously produce optically-active fluoro derivatives, which are important intermediates of medicines, agricultural chemicals and optical materials, specifically 4-fluoroproline derivatives, 2′-deoxy-2′-fluorouridine derivatives, optically-active α-fluorocarboxylate derivatives, and the like, even in a large scale.

  发现可以通过在有机碱或有机碱和“含有有机碱和氢氟酸盐或复合物”的情况下，将羟基衍生物与亚磺酰氟（SO2F2）反应来生产氟衍生物。根据目前的生产工艺，不需要使用不适合工业用途的全氟烷基磺酰氟，而且即使在大规模生产中，也可以优势地生产重要的药物、农药和光学材料的光学活性氟衍生物，特别是4-氟脯氨酸衍生物、2'-脱氧-2'-氟尿苷衍生物、光学活性α-氟羧酸酯衍生物等。
• Oxa-and thia(di)azabicyclic compounds
  申请人：E. I. du Pont de Nemours and Company

  公开号：US05712225A1

  公开（公告）日：1998-01-27

  The present invention relates to oxa(di)azabicyclic and thia(di)azabicyclic compounds, a method for their preparation and their use as herbicides.

  本发明涉及氧杂二氮杂双环和硫杂二氮杂双环化合物，一种制备它们的方法以及它们作为除草剂的应用。
• Dehydroxyfluorination agent
  申请人：Central Glass Company, Limited

  公开号：US08058412B2

  公开（公告）日：2011-11-15

  There is provided a novel, useful dehydroxyfluorination agent containing sulfuryl fluoride (SO2F2) and an organic base that is free from a free hydroxyl group in the molecule. According to the present dehydroxyfluorination agent, it is not necessary to use perfluoroalkanesulfonyl fluoride, which is not preferable in large-scale use, and it is possible to advantageously produce optically-active fluoro derivatives, which are important intermediates of medicines, agricultural chemicals and optical materials, for example, 4-fluoroproline derivatives, 2′-deoxy-2′-fluorouridine derivatives, optically-active α-fluorocarboxylate derivatives, and monofluoromethyl derivatives, even in large scale.

  提供了一种新颖、有用的去羟基氟化剂，它含有亚磺酰氟（SO2F2）和有机碱，该有机碱分子中没有自由羟基。根据这种去羟基氟化剂，不需要使用不适合大规模使用的全氟烷基磺酰氟，而且即使在大规模生产中也可以优势地生产出光学活性的氟衍生物，这些氟衍生物是药物、农业化学品和光学材料的重要中间体，例如4-氟脯氨酸衍生物、2'-去氧-2'-氟尿苷衍生物、光学活性的α-氟羧酸酯衍生物和单氟甲基衍生物。