ethyl benzo[b]furan-5-carboxylate | 127527-76-8

• 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 benzo[b]furan-5-carboxylate
• 英文别名: ethyl benzofuran-5-carboxylate；5-ethoxycarbonylbenzofuran；5-carboethoxybenzofuran；ethyl 1-benzofuran-5-carboxylate
• CAS: 127527-76-8
• 化学式: C₁₁H₁₀O₃
• mdl: MFCD00798563
• 分子量: 190.199
• InChiKey: NLIFMAOINVWKNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl benzo[b]furan-5-carboxylate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 生成 1-苯并呋喃-5-甲醇
  参考文献：
  名称：

  使用钯/铜/锂三元系统对偕二氟亚甲基进行去对称化，用于立体发散​​合成氟化氨基酸

  摘要：

  开发了使用钯/铜/锂三元系统的偕二氟亚甲基的去对称化，用于手性氟化氨基酸的立体发散合成。该三元系统以立体发散的方式以良好的产率提供了烯丙基和苄基取代的氟化 α-氨基酸，并具有优异的立体选择性（高达 >99 % ee 和 >20 : 1 dr）

  DOI：

  10.1002/anie.202313838
• 作为产物：
  描述：

  ethyl 4-(2,2-diethoxyethoxy)benzoate 在 tin-exchanged H-b zeolite (Sn-b) 作用下， 反应 4.0h， 以71%的产率得到ethyl benzo[b]furan-5-carboxylate
  参考文献：
  名称：

  通过2-芳氧基乙醛缩醛的分子内环化反应，沸石催化合成2,3-未取代的苯并[ b ]呋喃

  摘要：

  通过2-芳氧基乙醛缩醛的分子内环化，已经建立了一种有效的，对环境无害的非均相催化方法，用于合成2,3-未取代的苯并[ b ]呋喃。通过使用锡交换的H-β沸石（Sn-β）作为催化剂，可以以良好或极好的收率制备各种功能化的2,3-未取代的苯并[ b ]呋喃。Sn-β沸石催化剂还在间位取代的2-芳氧基乙醛缩醛的环化上表现出优异的形状选择性，并且优选形成高达97％的区域选择性的6-取代的异构体。而且，Sn-β沸石可以容易地回收和再利用而没有任何明显的活性损失。

  DOI：

  10.1016/j.tet.2015.05.029

文献信息

• Visible light-induced monofluoromethylenation of heteroarenes with ethyl bromofluoroacetate
  作者：Wei Yu、Xiu-Hua Xu、Feng-Ling Qing

  DOI：10.1039/c6nj00281a

  日期：——

  A mild approach for the direct introduction of an ethoxycarbonylmonofluoromethyl group into heteroarenes via visible light photocatalysis has been developed.

  已经开发了一种通过可见光光催化将乙氧基羰基单氟甲基基团直接引入杂芳烃的温和方法。
• Copper-catalyzed direct alkylation of heteroarenes
  作者：Cédric Theunissen、Jianjun Wang、Gwilherm Evano

  DOI：10.1039/c6sc05622a

  日期：——

  process is reported for the direct alkylation of C–H bonds in heteroarenes, privileged scaffolds in many areas of science. This reaction is based on the copper-catalyzed addition of alkyl radicals generated from activated secondary and tertiary alkyl bromides to a wide range of arenes, including furans, thiophenes, pyrroles, and their benzo-fused derivatives, as well as coumarins and quinolinones.

  据报道，杂芳烃中的 C-H 键直接烷基化是一种有效且广泛适用的方法，杂芳烃是许多科学领域的特殊支架。该反应基于铜催化的由活化的仲烷基溴和叔烷基溴产生的烷基自由基与多种芳烃的加成反应，包括呋喃、噻吩、吡咯及其苯并稠合衍生物，以及香豆素和喹啉酮。
• Development of a General and Selective Nanostructured Cobalt Catalyst for the Hydrogenation of Benzofurans, Indoles and Benzothiophenes
  作者：Bei Zhou、Vishwas G. Chandrashekhar、Zhuang Ma、Carsten Kreyenschulte、Stephan Bartling、Henrik Lund、Matthias Beller、Rajenahally V. Jagadeesh

  DOI：10.1002/anie.202215699

  日期：2023.3

  Pyrolysis of Co-DABCO-citric acid template on silica resulted in stable and reusable Co/Co3O4 core–shell nanostructured catalyst which allows for the selective hydrogenation of benzofurans as well as indoles and benzothiophenes.

  Co-DABCO-柠檬酸模板在二氧化硅上的热解产生稳定且可重复使用的 Co/Co 3 O 4核壳纳米结构催化剂，该催化剂允许苯并呋喃以及吲哚和苯并噻吩的选择性氢化。
• Identification of MK-944a:  A Second Clinical Candidate from the Hydroxylaminepentanamide Isostere Series of HIV Protease Inhibitors
  作者：Bruce D. Dorsey、Colleen McDonough、Stacey L. McDaniel、Rhonda B. Levin、Christina L. Newton、Jacob M. Hoffman、Paul L. Darke、Joan A. Zugay-Murphy、Emilio A. Emini、William A. Schleif、David B. Olsen、Mark W. Stahlhut、Carrie A. Rutkowski、Lawrence C. Kuo、Jiunn H. Lin、I-W. Chen、Stuart R. Michelson、M. Katharine Holloway、Joel R. Huff、Joseph P. Vacca

  DOI：10.1021/jm9903848

  日期：2000.9.1

  Recent results from human clinical trials have established the critical role of HIV protease inhibitors in the treatment of acquired immune-deficiency syndrome (AIDS). However, the emergence of viral resistance, demanding treatment protocols, and adverse side effects have exposed the urgent need for a second generation of HIV protease inhibitors. The continued exploration of our hydroxylaminepentanamide (HAPA) transition-state isostere series of HIV protease inhibitors, which initially resulted in the identification of Crixivan (indinavir sulfate, MK-639, L-735,524), has now yielded MK-944a (L-756,423). This compound is potent, is selective, and competitively inhibits HIV-1 PR with a Ki value of 0.049 nM. It stops the spread of the HIVIIIb-infected MT4 lymphoid cells at 25.0-50.0 nM, even in the presence of alpha(1) acid glycoprotein, human serum albumin, normal human serum, or fetal bovine serum. MK-944a has a longer half-life in several animal models (rats, dogs, and monkeys) than indinavir sulfate and is currently in advanced human clinical trials.
• Reaction of alkyl-3-nitro-and-3-bromo-3-nitroacrylates with 2-(2-nitroethenyl)furan
  作者：V. M. Berestovitskaya、N. A. Anisimova、O. N. Kataeva、G. A. Berkova、A. Jager

  DOI：10.1134/s1070363208050216

  日期：2008.5

  The diene condensation of beta-nitro and beta-bromo-beta-nitroacrylates with 2-(2-nitroethenyl)furan as 1,3-diene leads to a mixture of regioisomeric tetrahydrobenzofurans transforming under the reaction conditions into benzofurancarboxylates due to the easy dehydrohalogenation, denitration, and dehydration. In the case of a gem-bromonitroacrylate reaction takes two routes: diene synthesis and alkylation of the furan ring, the latter process prevailing. The structure of products formed was established by spectral methods. The investigation of geometry of 2-(1-methoxycarbonyl-2-nitroethenyl)-5-(2-nitroethenyl)furan by XRD analysis showed that its vinyl fragments have the coplanar chelate-like structure with the cisoid orientation of the CO2Me and NO2 groups. The ester group deviates from the plane of the the carbon-carbon multiple bond.