3,4-dichloro-5-(3'-hydroxypropylamino)-2(5H)-furanone | 1246528-98-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 3,4-dichloro-5-(3'-hydroxypropylamino)-2(5H)-furanone
• 英文别名: 3,4-dichloro-2-(3-hydroxypropylamino)-2H-furan-5-one
• CAS: 1246528-98-2
• 化学式: C₇H₉Cl₂NO₃
• 分子量: 226.059
• InChiKey: VMRWHWSTGDHEPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-dichloro-5-(3'-hydroxypropylamino)-2(5H)-furanone 、 3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 在 三苯基膦氢溴酸盐 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以60%的产率得到3-(3,4-dichloro-5-oxo-2,5-dihydrofuran-2-ylamino)propyl 3,4-di-O-acetyl-2,6-dideoxy-β-L-arabinohexopyranoside
  参考文献：
  名称：

  Convenient Synthesis of 3,4-Dichloro-5-hydroxy-2(5H)-Furanone Glycoconjugates

  摘要：

  在二异丙基乙胺（Hünig碱）存在下，用甲基氯甲酸酯处理3,4-二氯-5-羟基-2(5H)-呋喃酮，得到相应的碳酸盐。不稳定的甲氧羰氧基顺利地被氨基醇取代。用三苯基氢溴化磷作为催化剂，将得到的5-(w-羟基烷基氨基)黏氯酸衍生物与过乙酰化葡糖苷反应，得到标题中的多氯酸糖苷。

  DOI：

  10.3390/molecules16021011
• 作为产物：
  描述：

  (3,4-二氯-5-氧代-2H-呋喃-2-基)乙酸酯 、 3-氨基-1-丙醇 以 二氯甲烷 为溶剂， 以40%的产率得到3,4-dichloro-5-(3'-hydroxypropylamino)-2(5H)-furanone
  参考文献：
  名称：

  Synthesis and preliminary bioactivity assays of 3,4-dichloro-5-(ω-hydroxyalkylamino)-2(5H)-furanones

  摘要：

  5-(omega-Hydroxyalkylamino) derivatives of mucochloric acids were synthesized through a facile substitution reaction of 3,4-dichloro-5-hydroxy-2(5H)-furanone (mucochloric acid) acetate or 5-methylcarbonate with an appropriate amino alcohol or aminodiol. The obtained products were characterized and screened for their antibacterial and antiprotozoal activities. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.05.055

文献信息

• Synthesis and preliminary bioactivity assays of 3,4-dichloro-5-(ω-hydroxyalkylamino)-2(5H)-furanones
  作者：Edyta Gondela、Krzysztof Z. Walczak

  DOI：10.1016/j.ejmech.2010.05.055

  日期：2010.9

  5-(omega-Hydroxyalkylamino) derivatives of mucochloric acids were synthesized through a facile substitution reaction of 3,4-dichloro-5-hydroxy-2(5H)-furanone (mucochloric acid) acetate or 5-methylcarbonate with an appropriate amino alcohol or aminodiol. The obtained products were characterized and screened for their antibacterial and antiprotozoal activities. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Convenient Synthesis of 3,4-Dichloro-5-hydroxy-2(5H)-Furanone Glycoconjugates
  作者：Edyta Gondela、Krzysztof Z. Walczak

  DOI：10.3390/molecules16021011

  日期：——

  3,4-Dichloro-5-hydroxy-2(5H)-furanone treated with methyl chloroformate in the presence of diisopropylethylamine (Hünig’s base) gave the corresponding carbonate. The labile methoxycarbonyloxy group smoothly undergoes substitution by amino alcohols. The obtained 5-(w-hydroxyalkylamino) mucochloric acid derivatives reacted with peracetylated glucals using triphenylphosphine hydrobromide as a catalyst to give the title muchloric acid glycoconjugates.

  在二异丙基乙胺（Hünig碱）存在下，用甲基氯甲酸酯处理3,4-二氯-5-羟基-2(5H)-呋喃酮，得到相应的碳酸盐。不稳定的甲氧羰氧基顺利地被氨基醇取代。用三苯基氢溴化磷作为催化剂，将得到的5-(w-羟基烷基氨基)黏氯酸衍生物与过乙酰化葡糖苷反应，得到标题中的多氯酸糖苷。