2,3,4-trichlorodihydrofuran-1-one | 19714-00-2

• 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: 2,3,4-trichlorodihydrofuran-1-one
• 英文别名: 3,4,5-trichloro-2(5H)-furanone；mucochloryl chloride；3,4,5-trichloro-5H-furan-2-one；(+/-)-2,3,4-trichloro-4-hydroxy-cis-crotonic acid-lactone; mucochloric acid-chloride；(+/-)-2,3,4-Trichlor-4-hydroxy-cis-crotonsaeure-lacton; Mucochlorsaeure-chlorid；3,4,5-Trichlorofuran-2(5H)-one；2,3,4-trichloro-2H-furan-5-one
• CAS: 19714-00-2
• 化学式: C₄HCl₃O₂
• mdl: MFCD20547707
• 分子量: 187.41
• InChiKey: PEWMZNOPDLTYGE-UHFFFAOYSA-N

物化性质

• 沸点：
  109 °C(Press: 21 Torr)
• 密度：
  1.73±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3,4-trichlorodihydrofuran-1-one 在 sodium azide 作用下， 以 甲醇 为溶剂， 以94%的产率得到4-azido-3,5-dichlor-2(5H)-furanon
  参考文献：
  名称：

  Jaehnisch, Klaus; Ambrosi, Horst-Dieter, Journal fur praktische Chemie (Leipzig 1954), 1990, vol. 332, # 2, p. 233 - 240

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4-二氯-5-羟基-5H-呋喃-2-酮 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 2,3,4-trichlorodihydrofuran-1-one
  参考文献：
  名称：

  [EN] COMPOSITIONS AND METHODS FOR VIRAL SENSITIZATION
  [FR] COMPOSITIONS ET MÉTHODES DE SENSIBILISATION VIRALE

  摘要：

  提供了一些化合物，通过增加病毒在细胞中的传播、增加细胞中病毒的滴度或增加病毒中抗原的表达、基因或转基因表达、或细胞中病毒蛋白的表达来增强病毒的功效。还提供了其他用途、组合物和使用方法。

  公开号：

  WO2016119051A1

文献信息

• Hydroxylamine and Pseudoacyl Systems: Pseudo-oximes
  作者：Anna M. Daniels、Megan A. Supinski、Daniel P. Kennedy、William D. Robinson、Edward J. Valente

  DOI：10.1007/s10870-012-0377-7

  日期：2013.1

  Unhindered furan pseudoacyl chlorides react with hydroxylamine and a carbonate base to form oxidized cyclic N-hydroxyiminoimides. Thus, 3-chloroisobenzofuran-1-one forms 3-hydroximinoisoindolin-1-one (4) C8H6N2O2. Molecules are nearly planar and E-secondary amides hydrogen-bond with oximes through N(H)···N 2.920 Å and O(H)···O 2.720 Å contacts, and form infinite chains. Mucochloryl chloride (2,3,4-trichlorodihydrofuran-1-one) forms a similar hydroxyiminoimide (5E)-3,4-dichloro-5-hydroxyiminopyrrol-2-one (6), C4H2Cl2N2O2. However, opianic acid forms a mixture of mostly N-hydroxyphthalimide [6,7-dimethoxy-N-hydroxyisoindolin-1,3-dione (9)], C10H10N2O2, with small amounts of open oxime carboxylate [potassium 2,3-dimethoxy-6-(N-hydroxymethanoyl)benzoate (8) C10H10NO5K], and 2,3-dimethoxyphthalimide (10), C10H9NO4. These results suggest an intermediate pseudo-oxime, and such a derivative has been made in quantitative yield in a dehydration resistant arylpyran pseudoacyl system. 3-Chloro-4,4-dimethylisobenzopyran-1-one reacts with two equivalents of hydroxylamine and a carbonate base to form 2-hydroxy-3-(hydroxyamino)-4,4-dimethyl-3H-isoquinolin-1-one (14), C11H13N2O3, a pseudo-oxime. Pairs of pseudo-oximes form four hydrogen-bonds in two complementary sets, with N(H)···O 3.008 Å and O(H)···O 2.685 Å. Molecules are also linked in chains by hydrogen-bonds with O(H)···O 2.696 Å. These products have been characterized by spectroscopy and X-ray diffraction. .

  无阻碍的呋喃假酰基氯与羟胺和碳酸盐碱反应生成氧化的环状 N-羟基亚胺。因此，3-氯异苯并呋喃-1-酮形成 3-hydroximinoisoindolin-1-one (4) C8H6N2O2。分子几乎是平面的，E-仲酰胺通过 N(H)--N 2.920 Å 和 O(H)--O 2.720 Å 接触与肟形成氢键，并形成无限链。Mucochlory chloride（2,3,4-三氯二氢呋喃-1-酮）会形成类似的羟基亚氨基亚胺 (5E)-3,4-二氯-5-羟基亚氨基吡咯-2-酮 (6)，即 C4H2Cl2N2O2。然而，阿片酸形成的混合物主要是 N-羟基邻苯二甲酰亚胺[6,7-二甲氧基-N-羟基异吲哚啉-1,3-二酮（9）]（C10H10N2O2），以及少量开放的肟羧酸盐[2,3-二甲氧基-6-（N-羟基甲酰）苯甲酸钾（8）C10H10NO5K]和 2,3-二甲氧基邻苯二甲酰亚胺（10）（C10H9NO4）。这些结果表明存在一种中间假肟，而且这种衍生物已在耐脱水芳基吡喃假酰基体系中定量制得。3-氯-4,4-二甲基异苯并呋喃-1-酮与两当量的羟胺和碳酸盐碱反应生成 2-羟基-3-（羟基氨基）-4,4-二甲基-3H-异喹啉-1-酮 (14)，C11H13N2O3，这是一种假肟。成对的假肟在两个互补组中形成四个氢键，N(H)--O 为 3.008 埃，O(H)--O 为 2.685 埃。分子还通过氢键连接成链，O(H)--O 2.696 埃。这些产品已通过光谱学和 X 射线衍射进行了表征。.
• A New Synthesis of Novel Tricyclic 2(5H)-Furanone Heterocycles from 3,4,5-Trichloro-2(5H)-furanone
  作者：Mao-Sheng Cheng、Dan-Dan Ma、Yu Sha、Feng Li、Jian Ren

  DOI：10.3987/com-10-11923

  日期：——

  A novel class of five-six-six tricyclic 2(5H)-furanone heterocycles was synthesized from 3,4,5-trichloro-2(5H)-furanone and bifunctional o-nucleophiles in a single step. In addition, 2-(chloromethyl)quinoxaline was obtained through this method, and the distinctive formation mechanism of this compound is discussed.

  由 3,4,5-trichloro-2(5H)-furanone 和双功能 o-nucleophiles 在一个步骤中合成了一类新型的五六六三环 2(5H)-呋喃酮杂环。此外，通过该方法得到了2-(氯甲基)喹喔啉，并讨论了该化合物独特的形成机理。
• 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。
• Duczek, Wolfram; Jaehnisch, Klaus; Kunath, Annamarie, Liebigs Annalen der Chemie, 1992, # 8, p. 781 - 788
  作者：Duczek, Wolfram、Jaehnisch, Klaus、Kunath, Annamarie、Reck, Guenter、Winter, Gabriele、Schulz, Burkhard

  DOI：——

  日期：——
• Polezhaeva, N. A.; Sakhibullina, V. G.; El'shina, E. V., Russian Journal of General Chemistry, 1993, vol. 63, # 11.1, p. 1681 - 1683
  作者：Polezhaeva, N. A.、Sakhibullina, V. G.、El'shina, E. V.、Kostyunina, T. G.、Arbuzov, B. A.

  DOI：——

  日期：——

表征谱图