5-fluoro-4-methylumbelliferone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 5-fluoro-4-methylumbelliferone
• 英文别名: 5-Fluoro-7-hydroxy-4-methylchromen-2-one
• 化学式: C₁₀H₇FO₃
• 分子量: 194.162
• InChiKey: WNHWZWDFHWRARY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-fluoro-4-methylumbelliferone 、 β-D-葡萄糖五乙酸酯 在 4-二甲氨基吡啶 、 三氟化硼乙醚 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 生成 5’-fluoro-4’-methylumbelliferyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 、 5’-fluoro-4’-methylumbelliferyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  [EN] FLUORINATED 4' ALKYLUMBELLIFERYL α-D-GLUCOPYRANOSIDES, BIOLOGICAL STERILIZATION INDICATORS INCLUDING THE SAME AND METHODS OF USING THE SAME
  [FR] 4' ALKYLUMBELLIFERYL α-D-GLUCOPYRANOSIDES FLUORÉS, INDICATEUR DE STÉRILISATION BIOLOGIQUE LES COMPRENANT ET PROCÉDÉS D'UTILISATION ASSOCIÉS

  摘要：

  一个独立的生物灭菌指示器包括：一个外壳；包含细菌孢子的、和/或能够产生能催化酶底物裂解的酶的细菌孢子；以及一个易碎容器，其中容器内含有一种组合物，该组合物包括酶底物，如果易碎容器破裂，组合物将接触到细菌孢子以形成具有初始pH在6.0至9.0范围内的混合物。酶底物包括一种由结构式(I)表示的氟代的4'-烷基炔香豆蔻基α-D-葡萄糖吡喃苷，其中R1和R2中的一个是F，另一个是H，R3是具有1至12个碳原子的烷基。还公开了一种包含孤立组分的套件的生物灭菌指示器，其中组分包括（i）包含细菌孢子的、和/或能够产生能催化酶底物裂解的酶的细菌孢子，以及一种评估灭菌过程有效性的方法。

  公开号：

  WO2020115661A1
• 作为产物：
  描述：

  1,3-二甲氧基-5-氟苯 在 甲烷磺酸 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 5-fluoro-4-methylumbelliferone
  参考文献：
  名称：

  [EN] FLUORINATED 4' ALKYLUMBELLIFERYL α-D-GLUCOPYRANOSIDES, BIOLOGICAL STERILIZATION INDICATORS INCLUDING THE SAME AND METHODS OF USING THE SAME
  [FR] 4' ALKYLUMBELLIFERYL α-D-GLUCOPYRANOSIDES FLUORÉS, INDICATEUR DE STÉRILISATION BIOLOGIQUE LES COMPRENANT ET PROCÉDÉS D'UTILISATION ASSOCIÉS

  摘要：

  一个独立的生物灭菌指示器包括：一个外壳；包含细菌孢子的、和/或能够产生能催化酶底物裂解的酶的细菌孢子；以及一个易碎容器，其中容器内含有一种组合物，该组合物包括酶底物，如果易碎容器破裂，组合物将接触到细菌孢子以形成具有初始pH在6.0至9.0范围内的混合物。酶底物包括一种由结构式(I)表示的氟代的4'-烷基炔香豆蔻基α-D-葡萄糖吡喃苷，其中R1和R2中的一个是F，另一个是H，R3是具有1至12个碳原子的烷基。还公开了一种包含孤立组分的套件的生物灭菌指示器，其中组分包括（i）包含细菌孢子的、和/或能够产生能催化酶底物裂解的酶的细菌孢子，以及一种评估灭菌过程有效性的方法。

  公开号：

  WO2020115661A1

文献信息

• Synthesis of novel fluorinated coumarins: Excellent UV-light excitable fluorescent dyes
  作者：Wei-Chuan Sun、Kyle R Gee、Richard P Haugland

  DOI：10.1016/s0960-894x(98)00578-2

  日期：1998.11

  Two new fluorinated fluorescent dyes, 6,8-difluoro-7-hydroxy-4-methylcoumarin (Marina Blue(TM)) and 3-carboxy-6,8-difluoro-7-hydroxycoumarin (Pacific Blue(TM)), exhibit excellent photophysical properties among a series of novel fluorinated 7-hydroxycoumarins. Most of these fluorinated coumarins have quantum yields (0.63 to 0.89) equal to or higher than that of the parent compound (0.63), which, in combination with their lower pK(a)s and higher photostability, make them superior fluorescent dyes fbr use as reporter molecules in biological systems. (C) 1998 Elsevier Science Ltd. All rights reserved.
• FLUORINATED 4' ALKYLUMBELLIFERYL ?-D-GLUCOPYRANOSIDES, BIOLOGICAL STERILIZATION INDICATORS INCLUDING THE SAME AND METHODS OF USING THE SAME
  申请人：3M Innovative Properties Company

  公开号：EP3891163A1

  公开（公告）日：2021-10-13
• FLUORINATED 4' ALKYLUMBELLIFERYL ALPHA-D-GLUCOPYRANOSIDES, BIOLOGICAL STERILIZATION INDICATORS INCLUDING THE SAME AND METHODS OF USING THE SAME
  申请人：3M Innovative Properties Company

  公开号：EP3891163B1

  公开（公告）日：2022-05-18
• Fluorinated 4'-Alkylumbelliferyl a-D-Glucopyranosides, Biological Sterilization Indicators Including The Same And Methods Of Using The Same
  申请人：3M INNOVATIVE PROPERTIES COMPANY

  公开号：US20220017939A1

  公开（公告）日：2022-01-20

  A self-contained biological sterilization indicator comprises: a housing; bacterial spores comprising, and/or capable of producing, an enzyme capable of catalyzing cleavage of an enzyme substrate; and a frangible container containing a composition, wherein the composition comprises the enzyme substrate, wherein if the frangible container is broken the composition will contact the bacterial spores to form a mixture having an initial pH in the range from 6.0 to 9.0. The enzyme substrate comprises a fluorinated 4′-alkylumbelliferyl α-D-glucopyranoside represented by the structural formula (I) wherein one of R 1 and R 2 is F and the other is H, and R 3 is an alkyl group having from 1 to 12 carbon atoms. A biological sterilization indicator comprising a kit containing isolated components comprising (i) bacterial spores comprising, and/or capable of producing, an enzyme capable of catalyzing cleavage of the enzyme substrate and a method of assessing efficacy of a sterilization process are also disclosed.
• [EN] FLUORINATED 4' ALKYLUMBELLIFERYL α-D-GLUCOPYRANOSIDES, BIOLOGICAL STERILIZATION INDICATORS INCLUDING THE SAME AND METHODS OF USING THE SAME<br/>[FR] 4' ALKYLUMBELLIFERYL α-D-GLUCOPYRANOSIDES FLUORÉS, INDICATEUR DE STÉRILISATION BIOLOGIQUE LES COMPRENANT ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：3M INNOVATIVE PROPERTIES CO

  公开号：WO2020115661A1

  公开（公告）日：2020-06-11

  A self-contained biological sterilization indicator comprises: a housing; bacterial spores comprising, and/or capable of producing, an enzyme capable of catalyzing cleavage of an enzyme substrate; and a frangible container containing a composition, wherein the composition comprises the enzyme substrate, wherein if the frangible container is broken the composition will contact the bacterial spores to form a mixture having an initial pH in the range from 6.0 to 9.0. The enzyme substrate comprises a fluorinated 4'-alkylumbelliferyl α-D-glucopyranoside represented by the structural formula (I) wherein one of R1 and R2 is F and the other is H, and R3 is an alkyl group having from 1 to 12 carbon atoms. A biological sterilization indicator comprising a kit containing isolated components comprising (i) bacterial spores comprising, and/or capable of producing, an enzyme capable of catalyzing cleavage of the enzyme substrate and a method of assessing efficacy of a sterilization process are also disclosed.

  一个独立的生物灭菌指示器包括：一个外壳；包含细菌孢子的、和/或能够产生能催化酶底物裂解的酶的细菌孢子；以及一个易碎容器，其中容器内含有一种组合物，该组合物包括酶底物，如果易碎容器破裂，组合物将接触到细菌孢子以形成具有初始pH在6.0至9.0范围内的混合物。酶底物包括一种由结构式(I)表示的氟代的4'-烷基炔香豆蔻基α-D-葡萄糖吡喃苷，其中R1和R2中的一个是F，另一个是H，R3是具有1至12个碳原子的烷基。还公开了一种包含孤立组分的套件的生物灭菌指示器，其中组分包括（i）包含细菌孢子的、和/或能够产生能催化酶底物裂解的酶的细菌孢子，以及一种评估灭菌过程有效性的方法。