4H-呋喃并[3,2-b]吡咯-5-羧酸,2-甲酰基-,甲基酯 | 164667-55-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡咯
• 中文名称: 4H-呋喃并[3,2-b]吡咯-5-羧酸,2-甲酰基-,甲基酯
• 英文名称: methyl 2-formyl-4H-furo[3,2-b]pyrrole-5-carboxylate
• CAS: 164667-55-4
• 化学式: C₉H₇NO₄
• 分子量: 193.159
• InChiKey: RDJJCRWCUARXEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  72.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4H-呋喃并[3,2-b]吡咯-5-羧酸,2-甲酰基-,甲基酯 在 哌啶 、 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.66h， 生成 Methyl 2-(3,3,6,6-tetramethyl-1(2H),8(7H)-dioxo-3,4,5,6-tetrahydro-9H-xanthen-9-yl)-4H-furo[3,2-b]pyrrole-5-carboxylate
  参考文献：
  名称：

  Reactions of Furo[2,3-b]pyrrole and Furo[3,2-b]pyrrole-Type Aldehydes

  摘要：

  描述了甲基2-甲氧基甲基基-6-甲醛基呋喃[2,3-b]吡咯-5-羧酸甲酯（1d）的合成。将甲基2-甲醛基呋喃[2,3-b]吡咯-5-羧酸甲酯1a-1d与马来酸二腈反应，得到甲基2-(2,2-二氰乙烯基)呋喃[2,3-b]吡咯-5-羧酸甲酯3a-3d，用氰乙酸甲酯制备甲基2-[2-氰基-2-(甲氧羰基)乙烯基]呋喃[2,3-b]吡咯-5-羧酸甲酯4a-4d，用2-呋喃乙酮腈制备甲基2-[2-氰基-2-(2-呋喃基)乙烯基]呋喃[2,3-b]吡咯-5-羧酸甲酯5a-5d。化合物1b-1d和甲基叠氮乙酸酯给出了适当的乙烯基叠氮化物6b-6d，用于制备取代的呋喃[2,3-b:4,5-b']二吡咯7b-7d。比较了呋喃[2,3-b]吡咯醛1a-1d和呋喃[3,2-b]吡咯醛2a-2c在它们与5,5-二甲基环己烷-1,3-二酮反应中的反应性。制备的甲基2-[双(4,4-二甲基-2,6-二氧代环己基)甲基]呋喃[2,3-b]吡咯-5-羧酸甲酯8a-8d及其异构体10a-10c环化为取代的辛氢萘9a-9d和11a-11c。使用微波辐射制备了甲基4-苄基-2-[(4,4-二甲基-2,6-二氧代环己-1-基亚甲基)甲基]呋喃[3,2-b]吡咯-5-羧酸甲酯（12）。

  DOI：

  10.1135/cccc19991135

文献信息

• Reactions of Substituted Furo[3,2-b]pyrrole-5-carbohydrazides Under Classical and Microwave Conditions
  作者：Renata Gašparová、Margita Lácová、Alžbeta Krutošíková

  DOI：10.1135/cccc20052101

  日期：——

  Substituted hydrazones 5 and 6 were synthesized by the reaction of the corresponding furo[3,2-b]pyrrole-5-carboxyhydrazides 1 with 6-substituted 4-oxochromene-3-carbaldehydes 2 and methyl 2-formylfuro[3,2-b]pyrrole-5-carboxylates 3 under microwave irradiation as well as by the classical method. The beneficial effect of the microwave irradiation on these reactions was a shortening of the reaction time and an increase in the yields. The reactions of 1 with 4-[(4-oxochromen-3-yl)methylidene]-2-phenyloxazol-5(4H)-one (4) were also studied. Compounds 7 or 8 were obtained, depending on the reaction temperature.

  通过微波辐射，将相应的呋喃[3,2-b]吡咯-5-羧酰肼 1 与6-取代的4-氧基色酮-3-甲醛 2 和甲基-2-甲酰基呋喃[3,2-b]吡咯-5-羧酸酯 3 反应，合成了取代肼酮 5 和 6。这些反应中微波辐射的有益效果是缩短了反应时间并提高了产率。此外，还研究了 1 与4-[(4-氧基色酮-3-基)甲亚甲基]-2-苯氧唑-5(4H)-酮 (4) 的反应。取决于反应温度，得到了化合物 7 或 8。
• Reactions of Substituted Furan-2-carboxaldehydes and Furo[b]pyrrole Type Aldehydes with Benzothiazolium Salts
  作者：Zita Puterová、Alžbeta Krutošíková、Antonín Lyčka、Tatiana Ďurčeková

  DOI：10.3390/90400241

  日期：——

  A series of new push-pull compounds were synthesised by reaction of 5-aryl- furan-2-carboxaldehydes and furo[b]pyrrole type aldehydes with benzothiazolium salts. These new condensation products represent highly conjugated systems that have potential biological activity. The reaction of furo[b]pyrrole type aldehydes with benzothiazolium salts give potential precursors of cyanine dyes.

  通过5-芳基-呋喃-2-甲醛和呋喃[b]吡咯型醛与苯并噻唑鎓盐的反应合成了一系列新的推挽化合物。这些新的缩合产物代表了具有潜在生物活性的高度共轭系统。呋喃[b]吡咯型醛与苯并噻唑鎓盐的反应产生花青染料的潜在前体。
• Reaction of Substituted Furan-2-carboxaldehydes and Furo[b]pyrrole Type Aldehydes with Hippuric Acid
  作者：Zita Puterová、Heinz Sterk、Alžbeta Krutošíková

  DOI：10.3390/90100011

  日期：——

  3-oxazol-5(4H)-ones were prepared by reactions of hippuric acid with substituted furan-2-carboxaldehydes or furo[b]pyrrole type aldehydes. The reactivity of various furan-2-carboxaldehyde derivatives in this reaction is discussed. The effect of microwave irradiation on some condensation reactions was compared with "classical" conditions. The results show that microwave irradiation shortens the reaction

  4-杂亚芳基-2-苯基-1,3-恶唑-5(4H)-酮是通过马尿酸与取代的呋喃-2-甲醛或呋喃[b]吡咯型醛反应制备的。讨论了该反应中各种呋喃-2-甲醛衍生物的反应性。将微波辐射对某些缩合反应的影响与“经典”条件进行了比较。结果表明，微波辐射缩短了反应时间，同时提供了相当的产率。元素分析、UV、IR 和 1D NMR 证明了新合成化合物的结构。2D NMR 光谱测量证实碳-碳双键处的构型对应于产物的纯 E 异构体。
• Dandia, Anshu; Indora, Aayushi; Parewa, Vijay, Indian Journal of Heterocyclic Chemistry, 2018, vol. 28, # 1, p. 103 - 112
  作者：Dandia, Anshu、Indora, Aayushi、Parewa, Vijay、Rathore, Kuldeep S.

  DOI：——

  日期：——
• Reactions of Furo[2,3-b]pyrrole and Furo[3,2-b]pyrrole-Type Aldehydes
  作者：Róbert Sleziak、Slávka Balážiová、Alžbeta Krutošíková

  DOI：10.1135/cccc19991135

  日期：——

  The synthesis of methyl 2-formyl-6-(methoxymethyl)furo[2,3-b]pyrrole-5-carboxylate (1d) is described. The reactions of methyl 2-formylfuro[2,3-b]pyrrole-5-carboxylates 1a-1d with malononitrile afforded methyl 2-(2,2-dicyanovinyl)furo[2,3-b]pyrrole-5-carboxylates 3a-3d, with methyl cyanoacetate methyl 2-[2-cyano-2-(methoxycarbonyl)vinyl]furo[2,3-b]pyrrole-5-carboxylates 4a-4d and with 2-furylacetonitrile methyl 2-[2-cyano-2-(2-furyl)vinyl]furo[2,3-b]pyrrole-5-carboxylates 5a-5d. Compounds 1b-1d and methyl azidoacetate gave the appropriate vinylazides 6b-6d, which were used for preparation of substituted furo[2,3-b:4,5-b']dipyrroles 7b-7d. Reactivity of furo[2,3-b]pyrrole aldehydes 1a-1d and furo[3,2-b]pyrrole aldehydes 2a-2c in their reactions with 5,5-dimethylcyclohexane-1,3-dione is compared. The prepared methyl 2-[bis(4,4-dimethyl-2,6-dioxocyclohexyl)methylfuro[2,3-b]pyrrole-5-carboxylates 8a-8d and their isomers 10a-10c cyclized into substituted octahydroxanthenes 9a-9d and 11a-11c, respectively. Methyl 4-benzyl-2- [(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)methyl]furo[3,2-b]pyrrole-5-carboxylate (12) was prepared using microwave irradiations.

  描述了甲基2-甲氧基甲基基-6-甲醛基呋喃[2,3-b]吡咯-5-羧酸甲酯（1d）的合成。将甲基2-甲醛基呋喃[2,3-b]吡咯-5-羧酸甲酯1a-1d与马来酸二腈反应，得到甲基2-(2,2-二氰乙烯基)呋喃[2,3-b]吡咯-5-羧酸甲酯3a-3d，用氰乙酸甲酯制备甲基2-[2-氰基-2-(甲氧羰基)乙烯基]呋喃[2,3-b]吡咯-5-羧酸甲酯4a-4d，用2-呋喃乙酮腈制备甲基2-[2-氰基-2-(2-呋喃基)乙烯基]呋喃[2,3-b]吡咯-5-羧酸甲酯5a-5d。化合物1b-1d和甲基叠氮乙酸酯给出了适当的乙烯基叠氮化物6b-6d，用于制备取代的呋喃[2,3-b:4,5-b']二吡咯7b-7d。比较了呋喃[2,3-b]吡咯醛1a-1d和呋喃[3,2-b]吡咯醛2a-2c在它们与5,5-二甲基环己烷-1,3-二酮反应中的反应性。制备的甲基2-[双(4,4-二甲基-2,6-二氧代环己基)甲基]呋喃[2,3-b]吡咯-5-羧酸甲酯8a-8d及其异构体10a-10c环化为取代的辛氢萘9a-9d和11a-11c。使用微波辐射制备了甲基4-苄基-2-[(4,4-二甲基-2,6-二氧代环己-1-基亚甲基)甲基]呋喃[3,2-b]吡咯-5-羧酸甲酯（12）。