(3,4-二氯-5-氧代-2H-呋喃-2-基)乙酸酯 | 63031-44-7

• 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
• 中文名称: (3,4-二氯-5-氧代-2H-呋喃-2-基)乙酸酯
• 英文名称: 5-acetoxy-3,4-dichloro-5H-furan-2-one
• 英文别名: 5-Acetoxy-3,4-dichloro-2(5H)-furanone；mucochloric acid acetate；5-Acetoxy-3,4-dichlor-5H-furan-2-on；4-acetoxy-2,3-dichloro-2-buten-4-olide；(3,4-dichloro-5-oxo-2H-furan-2-yl) acetate
• CAS: 63031-44-7
• 化学式: C₆H₄Cl₂O₄
• 分子量: 211.001
• InChiKey: HQHJOUFXKZWWIG-UHFFFAOYSA-N

物化性质

• 沸点：
  135-139 °C(Press: 15 Torr)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3,4-二氯-5-氧代-2H-呋喃-2-基)乙酸酯 、 异丙醇胺 以 二氯甲烷 为溶剂， 以58%的产率得到3,4-dichloro-5-(2'-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
• 作为产物：
  描述：

  3,4-二氯-5-羟基-5H-呋喃-2-酮 、 乙酸酐 在 amberlyst-15 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以97%的产率得到(3,4-二氯-5-氧代-2H-呋喃-2-基)乙酸酯
  参考文献：
  名称：

  Further Utilization of Mucohalic Acids:  Palladium-Free, Regioselective Etherification and Amination of α,β-Dihalo γ-Methoxycarbonyloxy and γ-Acetoxy Butenolides

  摘要：

  [GRAPHICS]Palladium-free etherification and amination of mucohalic acid methyl carbonates le (3,4-dichloro-5-methoxycarbonyloxy-5H-furan-2-one) and 1f (3,4-dibromo-5-methoxycarbonyloxy-5H-furan-2-one) and mucochloric acid acetate 1h (3,4-dichloro-5-acetoxy-5H-furan-2-one) was achieved to afford gamma-functionalized alpha,beta-unsaturated gamma-butyrolactones in good to excellent yield.

  DOI：

  10.1021/ol035994n

文献信息

• Preparation of substituted butenolides via palladium-free etherification and amination of masked mucohalic acids
  申请人：Blazecka Garth Peter

  公开号：US20050059831A1

  公开（公告）日：2005-03-17

  Methods and materials for preparing 4-substituted-2-buten-4-olides are disclosed. The methods include reacting a masked mucohalic acid with a primary or secondary amine or with an arylol in the presence of a base. Unlike existing processes, the disclosed methods do not require the use of palladium, which make them well suited for preparing intermediates in drug syntheses.

  公开了制备4-取代-2-丁烯-4-醇内酯的方法和材料。该方法包括在碱存在下将掩蔽的黏膜酸与一级或二级胺或芳基醇反应。与现有的方法不同，公开的方法不需要使用钯，这使它们非常适合用于制备药物合成中间体。
• Novel 4-amino-2(5H)-furanones
  申请人：Lattmann Eric

  公开号：US20070123718A1

  公开（公告）日：2007-05-31

  The present invention relates to compounds of formula (1): wherein X is selected from hydrogen, a halogen, a substituted or unsubstituted cyclic and heterocyclic moiety, substituted or unsubstituted, linear or branched alkyl, alkyloxy, alkylcarbonyl, alkyloxycarbonyl, alkenyl, alkenyloxy, alkenylcarbonyl, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylcarbonyl, alkynyloxycarbonyl, aryl, benzyl, arlyoxy, arylcarbonyl, aryloxycarbonyl and sulphur equivalents of said oxy, carbonyl and oxycarbonyl moieties, R is selected from hydrogen, a halogen, an amide, a substituted or unsubstituted cyclic and heterocyclic moiety, substituted or unsubstituted, linear or branched alkyl, alkyloxy, alkylcarbonyl, alkyloxycarbonyl, alkenyl, alkenyloxy, alkenylcarbonyl, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylcarbonyl, alkynyloxycarbonyl, aryl, benzyl, arlyoxy, arylcarbonyl, aryloxycarbonyl and sulphur equivalents of said oxy, carbonyl and oxycarbonyl moieties, and R 1 and R 2 arc each independently selected from H, C 1-18 straight, branched or cyclic, saturated, unsaturated and aromatic hydrocarbyl groups, which aromatic groups may be heterocyclic, cyclic or acyclic and which may optionally be substituted by alkyl, alkoxy, or halo; or R 1 and R 2 , when taken together with the N-atom to which they are bonded, may form an N-containing saturated, unsaturated or partially unsaturated ring system comprising 3 to 10 ring atoms selected from C, N and O, optionally substituted at any position of the ring by a substituent selected from a halogen, a substituted or unsubstituted cyclic and heterocyclic moiety, substituted or unsubstituted, linear or branched alkyl, alkyloxy, alkylcarbonyl, alkyloxycarbonyl, alkenyl, alkenyloxy, alkenylcarbonyl, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylcarbonyl, alkynyloxycarbonyl, aryl, benzyl, arlyoxy, arylcarbonyl, aryloxycarbonyl, sulphur equivalents of said oxy, carbonyl and oxycarbonyl moieties, and oxo. The invention also relates to their uses as CCK receptor ligands and CCK antagonists.

  本发明涉及式（1）的化合物：其中X选自氢，卤素，取代或未取代的环状和杂环状基团，取代或未取代的线性或支链烷基，烷氧基，烷基羰基，烷氧基羰基，烯基，烯氧基，烯基羰基，烯氧基羰基，炔基，炔氧基，炔基羰基，炔氧基羰基，芳基，苄基，芳基氧基，芳基羰基，芳基氧基羰基和上述氧，羰基和氧羰基基团的硫代替物，R选自氢，卤素，酰胺，取代或未取代的环状和杂环状基团，取代或未取代的线性或支链烷基，烷氧基，烷基羰基，烷氧基羰基，烯基，烯氧基，烯基羰基，烯氧基羰基，炔基，炔氧基，炔基羰基，炔氧基羰基，芳基，苄基，芳基氧基，芳基羰基，芳基氧基羰基和上述氧，羰基和氧羰基基团的硫代替物，R1和R2各自独立地选自H，C1-18直链，支链或环状，饱和，不饱和和芳香族烃基团，其中芳香族基团可以是杂环状，环状或非环状，并且可以选择性地被烷基，烷氧基或卤素取代；或当R1和R2与它们所连接的N原子一起形成含氮的饱和，不饱和或部分不饱和的环系统时，该环系统包括3至10个环原子，选自C，N和O，并且可以在环的任何位置上选择性地被取代基所取代，所述取代基选自卤素，取代或未取代的环状和杂环状基团，取代或未取代的线性或支链烷基，烷氧基，烷基羰基，烷氧基羰基，烯基，烯氧基，烯基羰基，烯氧基羰基，炔基，炔氧基，炔基羰基，炔氧基羰基，芳基，苄基，芳基氧基，芳基羰基，芳基氧基羰基，上述氧，羰基和氧羰基基团的硫代替物以及氧代。本发明还涉及它们作为CCK受体配体和CCK拮抗剂的用途。
• Selective amination of the mucohalic acid derivatives
  作者：Tian-Cai Li、Cou-Xi Chen、Xue-Qiang Li、Xiao-Hui Gao

  DOI：10.1016/j.cclet.2013.01.035

  日期：2013.3

  An efficient synthesis of 4,5-diamino-3-halofuran-2(5H)-ones has been developed based on a sequential acylation and bisamination of mucohalic acids. The beta- and gamma-amination products have also been prepared with high regioselectivity. This reaction shows some advantages in terms of its simple operation and readily available but highly functionalized starting material. All products gave satisfactory IR, H-1 NMR, C-13 NMR and HRMS. (C) 2013 Xue-Qiang Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Mucochloric Acid. I. Reactions of the Pseudo Acid Group
  作者：David T. Mowry

  DOI：10.1021/ja01162a056

  日期：1950.6
• KOKOSINSKI J.; GUMULKA W., ORGANIKA, 1977, WARSZAWA, 1977, 37-45
  作者：KOKOSINSKI J.、 GUMULKA W.

  DOI：——

  日期：——