Ethyl Benzofuro<3,2-b>pyrrole-2-carboxylate | 63285-32-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: Ethyl Benzofuro<3,2-b>pyrrole-2-carboxylate
• 英文别名: 2-Carbethoxy-benzofuro<3,2-b>pyrrol；1H-benzo[4,5]furo[3,2-b]pyrrole-2-carboxylic acid ethyl ester；Ethyl benzofuro[3,2-b]pyrrole-2-carboxylate；ethyl 1H-[1]benzofuro[3,2-b]pyrrole-2-carboxylate
• CAS: 63285-32-5
• 化学式: C₁₃H₁₁NO₃
• mdl: MFCD08531109
• 分子量: 229.235
• InChiKey: YWWQJOHGNNWROG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  55.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl Benzofuro<3,2-b>pyrrole-2-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以89%的产率得到苯并呋喃[3,2-b]吡咯-2-羧酸
  参考文献：
  名称：

  Synthesis and reactions of substituted benzofuro[3,2-b]pyrrole derivatives

  摘要：

  本文介绍了乙基苯并呋[3,2-b]吡咯-2-羧酸酯的制备、水解、N-烷基化和还原。同时描述了新的杂环系统苯并呋[3,2-b]吡咯和2H-二氢苯并呋[2',3':4,5]吡咯[1,2-d]-1,2,4-三嗪-1-酮的合成方法。通过红外、紫外、1H NMR、13C NMR和电子轰击质谱等手段确认了14种新物质的结构。

  DOI：

  10.1135/cccc19823288
• 作为产物：
  描述：

  2,3-苯并呋喃 在 sodium ethanolate 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 42.33h， 生成 Ethyl Benzofuro<3,2-b>pyrrole-2-carboxylate
  参考文献：
  名称：

  Synthesis and reactions of substituted benzofuro[3,2-b]pyrrole derivatives

  摘要：

  本文介绍了乙基苯并呋[3,2-b]吡咯-2-羧酸酯的制备、水解、N-烷基化和还原。同时描述了新的杂环系统苯并呋[3,2-b]吡咯和2H-二氢苯并呋[2',3':4,5]吡咯[1,2-d]-1,2,4-三嗪-1-酮的合成方法。通过红外、紫外、1H NMR、13C NMR和电子轰击质谱等手段确认了14种新物质的结构。

  DOI：

  10.1135/cccc19823288

文献信息

• Rigidified Compounds for Modulating Heparanase Activity
  申请人：Gelder M. Van Joel

  公开号：US20080039456A1

  公开（公告）日：2008-02-14

  Disclosed are novel rigidified compounds having a rhodanine-like residue and at least one aryl or heteroaryl residue linked to the rhodanine-like residue, whereby a core structure of these compounds, as defined in the specification, is characterized as having one or zero free-to-rotate bonds. Also disclosed are pharmaceutical compositions containing these rigidified compounds and uses thereof for modulating the activity of heparanase and hence in the treatment of heparanase-associated diseases and disorders, and uses thereof for modulating the activity of heparin-binding proteins and hence in the treatment of heparin-binding proteins-associated diseases and disorders as well as in the treatment of medical conditions that are at least partially treatable by rhodanine or a rhodanine analog.

  揭示了一种新颖的刚性化合物，其具有类似罗丹啉的残基和至少一个连接到类似罗丹啉残基的芳基或杂芳基残基，其中这些化合物的核心结构，如规范中定义的那样，其特征是具有一个或零个可自由旋转的键。还披露了含有这些刚性化合物的药物组合物以及用于调节肝素酶活性的用途，从而治疗与肝素酶相关的疾病和紊乱，并用于调节肝素结合蛋白的活性以及治疗与肝素结合蛋白相关的疾病和紊乱，以及治疗至少部分可通过罗丹啉或罗丹啉类似物治疗的医疗状况的用途。
• Synthesis of N-Phenylsulfonyl Protected Furo[3,2-b]pyrroles
  作者：Vladimír Bobošík、Alžbeta Krutošíková

  DOI：10.1135/cccc19940499

  日期：——

  Protection of nitrogen atom of heterocyclic molecules, such as indole and pyrrole types, enables various reactions of these systems. N-Phenylsulfonyl derivatives, which have been widely used for this purpose, were prepared in the indole series by the reaction of N-sodium and N-lithium salts with benzenesulfonyl chloride. This method requires waterfree and oxygenfree conditions. On the other hand, the phase transfer catalysis conditions used in this work obviates these disadvantages. We therefore selected the latter method for the preparation of variously substituted 4-phenylsulfonylfuro[3,2-b]pyrroles (I - VII) and 1-phenylsulfonylbenzo[b]furo[3,2-b]pyrroles (VIII - IX).

  保护杂环分子中的氮原子，如吲哚和吡咯类，可以使这些系统发生各种反应。已广泛用于此目的的N-苯磺酰衍生物，通过N-钠和N-锂盐与苯磺酰氯反应制备吲哚系列中。该方法需要无水和无氧条件。另一方面，本研究中使用的相转移催化条件消除了这些缺点。因此，我们选择了后一种方法来制备不同取代的4-苯磺酰基呋喃[3,2-b]吡咯（I-VII）和1-苯磺酰基苯并[ b]呋喃[3,2-b]吡咯（VIII-IX）。
• COMPELLED AZEPINE RING FORMATION IN THERMAL RING EXPANSION OF 2<i>H</i>-AZIRINE
  作者：Kazuaki Isomura、Hiroshi Taguchi、Tatsuyoshi Tanaka、Hiroshi Taniguchi

  DOI：10.1246/cl.1977.401

  日期：1977.4.5

  Thermolyses of three β-(benzofuran-2-yl)vinyl azides, 1a, 1b, and 1c, in which the benzofuran ring bears a hydrogen, a methyl, and a phenyl group at the 3-position, gave a benzofuropyrrole 2, a benzofuropyridine 3, and a benzofurobenzazepine 4, respectively. Photolyses of these azides gave the corresponding 2H-azirines, 7a, 7b and 7c, which on heating afforded the same heterocyclic compounds as the

  三个 β-（苯并呋喃-2-基）乙烯基叠氮化物 1a、1b 和 1c（其中苯并呋喃环在 3 位带有一个氢、一个甲基和一个苯基）的热解得到苯并呋喃吡咯 2，a分别是苯并呋喃吡啶 3 和苯并呋喃苯并氮杂 4。这些叠氮化物的光解得到相应的 2H-氮杂环化合物 7a、7b 和 7c，加热后得到与乙烯基叠氮化物热解产物相同的杂环化合物。
• Condensed O-, N-heterocycles by the transformation of azidoacrylates
  作者：Alzbeta Krutosikova、Miloslava Dandarova、Jana Chylova、Daniel Vegh

  DOI：10.1007/bf00812330

  日期：——

  A number of furo[3,2-c]pyridines (4 a-4 d) and benzo[b]derivative (4e), as well as pyrrolo[2',3'-4,5]furo[3,2-c]pyridine (8) were prepared by reaction of the corresponding iminophosphoranes, available from ethyl azidoheteroacrylates and triphenylphosphine, with phenyl isocyanate. The appropriate azidoheteroacrylates were used for the preparation of some substituted furo[3,2-b:4,5-b]dipyrroles (6). The reactions of the prepared compounds are described.
• KRUTOSIKOVA, A.;KOVAC, J.;DANDAROVA, M.;BOBALOVA, M., COLLECT. CZECH. CHEM. COMMUN., 1982, 47, N 12, 3288-3296
  作者：KRUTOSIKOVA, A.、KOVAC, J.、DANDAROVA, M.、BOBALOVA, M.

  DOI：——

  日期：——