3-chloro-4-(4-methoxyphenyl)-2(5H)-furanone | 441287-32-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-chloro-4-(4-methoxyphenyl)-2(5H)-furanone
• 英文别名: 3-chloro-4-(4-methoxyphenyl)furan-2(5H)-one；4-chloro-3-(4-methoxyphenyl)-2H-furan-5-one
• CAS: 441287-32-7
• 化学式: C₁₁H₉ClO₃
• 分子量: 224.644
• InChiKey: NQSDIMNENJQHDD-UHFFFAOYSA-N

物化性质

• 熔点：
  174-175 °C(Solv: dichloromethane (75-09-2); ligroine (8032-32-4))
• 沸点：
  402.7±45.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-chloro-4-(4-methoxyphenyl)-2(5H)-furanone 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以97%的产率得到3-chloro-4-(4-hydroxyphenyl)furan-2(5H)-one
  参考文献：
  名称：

  后期溴化使红布洛内酯 B、I、K 和 O 的合成成为可能

  摘要：

  从市售的 3,4-二氯-2(5H)-呋喃酮中分 3-4 步完成了海洋天然产物 rubrolides B、I、K 和 O 的简洁高效合成。关键步骤包括：(i) 位点选择性 Suzuki 交叉偶联，(ii) 乙烯醇缩合，以及 (iii) 后期溴化。后一反应允许以高度区域选择性的方式对芳环进行官能化，从而能够从常见前体快速获得目标红内酯。

  DOI：

  10.1002/ejoc.201600473
• 作为产物：
  描述：

  在 lithium chloro-isopropyl-magnesium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以65%的产率得到3-chloro-4-(4-methoxyphenyl)-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

• Palladium-catalyzed hydrodehalogenation of butenolides: An efficient and sustainable access to β-arylbutenolides
  作者：Milandip Karak、Luiz C.A. Barbosa、Celia R.A. Maltha、Thiago M. Silva、John Boukouvalas

  DOI：10.1016/j.tetlet.2017.06.016

  日期：2017.7

  69–92% yield by reductive dehalogenation of α-halo-β-arylbutenolides. The latter were assembled in a single-step from α,β-dihalobutenolides, which are accessible on a large-scale from biomass-derived furfural. Our dehalogenation protocol is illustrated by a new synthesis of the marine antibiotics rubrolide E and F, and 3″-bromorubrolide F.

  通过α-卤代-β-芳基丁烯化物的还原脱卤作用，已经制备了几种α-未取代的β-芳基丁烯化物，产率为69-92％。后者由α，β-二卤代丁烯内酯一步一步组装，可从生物质衍生的糠醛大规模获得。我们的脱卤方案通过海洋抗生素Rubrolide E和F，以及3''-溴代溴化物F的新合成来说明。
• 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 the human aldose reductase inhibitor rubrolide L
  作者：John Boukouvalas、Lucas C. McCann

  DOI：10.1016/j.tetlet.2010.06.129

  日期：2010.9

  The first synthesis of rubrolide L, a marine ascidian butenolide and a potent inhibitor of human aldose reductase, has been achieved by two tactically distinct pathways in 4–5 steps and 37–42% overall yield from commercially available 3-chlorotetronic acid.

  通过海洋上的海鞘丁烯内酯和有效的人醛糖还原酶抑制剂Rubrolide L的首次合成，是通过两种战术上不同的途径，以4-5个步骤完成的，而市售3-氯代十四酸的总产率为37-42％。
• 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.