3-chloro-4-(2-thienyl)-2(5H)-furanone

• 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-chloro-4-(2-thienyl)-2(5H)-furanone
• 英文别名: 3-chloro-4-thienyl-2(5H)-furanone；4-chloro-3-thiophen-2-yl-2H-furan-5-one
• 化学式: C₈H₅ClO₂S
• 分子量: 200.645
• InChiKey: NZKRMEJETRLAGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴-1-(2-THIENYL)-1-ETHANONE 在 吡啶 、 lithium chloro-isopropyl-magnesium chloride 、 sodium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 2.01h， 生成 3-chloro-4-(2-thienyl)-2(5H)-furanone
  参考文献：
  名称：

  Synthesis of α-Halobutenolides Using the Nucleophilicity of Magnesium Alkylidene Carbenoids

  摘要：

  alpha-Halobutenolides were synthesized from halomethyl p-tolyl sulfoxides, alpha-bromoketones, and phenyl chloroformate in three steps using the nucleophilicity of magnesium alkylidene carbenoids. The reaction of alpha-bromoketones with [halo(p-tolylsulfinyl)methyl]lithiums and the subsequent basification of the reaction mixture using an aqueous NaOH solution afforded 1-chloro-3-hydroxyprop-1-enyl p-tolyl sulfoxides in 83-99% yield. A phenoxycarbonyl group was then introduced to the hydroxyl group of the sulfoxides by reacting with phenyl chloroformate in the presence of pyridine. The sulkodde/magnesium exchange reaction of the cyclization precursors with i-PrMgCl center dot LiCl led to the formation of alpha-halobutenolides in moderate to good yields.

  DOI：

  10.3987/com-14-s(k)60

文献信息

• Mucochloric Acid: A Useful Synthon for the Selective Synthesis of 4-Aryl-3-chloro-2(5H)-furanones, (Z)-4-Aryl-5-[1-(aryl)methylidene]-3-chloro-2(5H)-furanones and 3,4-Diaryl-2(5H)-furanones
  作者：Fabio Bellina、Chiara Anselmi、Francesca Martina、Renzo Rossi

  DOI：10.1002/ejoc.200300097

  日期：2003.6

  4-Dichloro-2(5H)-furanone, which has been prepared efficiently from mucochloric acid, has been transformed selectively into 4-aryl-3-chloro-2(5H)-furanones either by Suzuki- or Stille-type reactions. These monochloro derivatives have been used as precursors either to (Z)-4-aryl-5-[1-(aryl)methylidene]-3-chloro-2(5H)-furanones, including naturally occurring rubrolide M, or to unsymmetrical 3,4-diaryl-2(5H)-furanones

  由粘氯酸有效制备的3,4-二氯-2（5 H）-呋喃酮已通过Suzuki-或Stille-选择性地转化为4-芳基-3-氯-2（5 H）-呋喃酮类型反应。这些一氯衍生物已被用作（Z）-4-芳基-5- [1-（芳基）亚甲基] -3-氯-2（5 H）-呋喃酮的前体，包括天然存在的罗布洛尔M，或不对称的前体。 3，4-二芳基-2（5 H）-呋喃酮。约2（5 H已经发现，如此制备的呋喃酮衍生物在体外对NCI三细胞系面板表现出显着的细胞毒性活性，但是对NCI人肿瘤60细胞系面板的细胞毒性有限。（©Wiley-VCH Verlag GmbH＆Co.KGaA，69451 Weinheim，Germany，2003）
• Total synthesis of rubrolide M and some of its unnatural congeners
  作者：Fabio Bellina、Chiara Anselmi、Renzo Rossi

  DOI：10.1016/s0040-4039(02)00202-2

  日期：2002.3

  Two protocols have been developed for the Pd-catalyzed regioselective synthesis of 4-aryl-3-chloro-2(5H)-furanones starting from 3,4-dichloro-2(5H)-furanone. These monochloro derivatives have then been used as precursors to (Z)-4-aryl-5-[1-(aryl)methylidene]-3-chloro-2(5H)-furanones including naturally-occurring rubrolide M.

  已经开发了用于从3,4-二氯-2（5 H）-呋喃酮开始Pd催化的4-芳基-3-氯2（5 H）-呋喃酮的区域选择性合成的两种方案。这些一氯衍生物随后被用作（Z）-4-芳基-5- [1-（芳基）亚甲基] -3-氯-2（5 H）-呋喃酮的前体，包括天然存在的罗布洛尔M。
• Synthesis of α-Halobutenolides Using the Nucleophilicity of Magnesium Alkylidene Carbenoids
  作者：Tsuyoshi Satoh、Tsutomu Kimura、Kazuki Fukuda、Gaku Kashiwamura

  DOI：10.3987/com-14-s(k)60

  日期：——

  alpha-Halobutenolides were synthesized from halomethyl p-tolyl sulfoxides, alpha-bromoketones, and phenyl chloroformate in three steps using the nucleophilicity of magnesium alkylidene carbenoids. The reaction of alpha-bromoketones with [halo(p-tolylsulfinyl)methyl]lithiums and the subsequent basification of the reaction mixture using an aqueous NaOH solution afforded 1-chloro-3-hydroxyprop-1-enyl p-tolyl sulfoxides in 83-99% yield. A phenoxycarbonyl group was then introduced to the hydroxyl group of the sulfoxides by reacting with phenyl chloroformate in the presence of pyridine. The sulkodde/magnesium exchange reaction of the cyclization precursors with i-PrMgCl center dot LiCl led to the formation of alpha-halobutenolides in moderate to good yields.