ethyl 7-methylbenzofuran-2-carboxylate | 53715-90-5

• 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 7-methylbenzofuran-2-carboxylate
• 英文别名: ethyl 7-methyl-1-benzofuran-2-carboxylate
• CAS: 53715-90-5
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: TXCDILNMVQWLIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  ethyl 7-methylbenzofuran-2-carboxylate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 0.75h， 生成 7-methylbenzofuran-2-carboxylic acid
  参考文献：
  名称：

  .alpha.-Adrenoceptor reagents. 2. Effects of modification of the 1,4-benzodioxan ring system on .alpha.-adrenoreceptor activity

  摘要：

  Modification of the 1,4-benzodioxan ring present in RX 781094 has not previously been considered. This paper describes a number of analogues of this ring system, including compounds in which one of the oxygen atoms has been replaced by a methylene group and also those in which the ring size has been changed to give, for example, furan and thiophene derivatives. The dihydrobenzofuranylimidazoline compound 7 is the only analogue possessing presynaptic antagonist potency potency and selectivity comparable to that of 1. In view of this result, a number of derivatives was prepared to determine the structure-activity relationships within this series. Many derivatives, as well as the parent compound 7, were found to possess presynaptic alpha 2-adrenoreceptor antagonist and postsynaptic alpha 1-adrenoreceptor partial agonist properties. Two of the selective presynaptic antagonists, 13 and 14 possess greater potency and selectivity than that possessed by 1. The 5-chloro derivative 25 is twice as potent as after oral administration but only about half as potent when given intravenously.

  DOI：

  10.1021/jm00371a003
• 作为产物：
  描述：

  邻甲酚 在 caesium carbonate 、 三乙胺 、 magnesium chloride 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 72.25h， 生成 ethyl 7-methylbenzofuran-2-carboxylate
  参考文献：
  名称：

  通过催化不对称亨利反应 有效合成手性苯并呋喃基β-氨基醇†

  摘要：

  手性β氨基醇配体小号被发现有效地用于铜（II）催化苯并呋喃-2- carbaldehydes与硝基甲烷，而导致的（形成的不对称Henry反应小号）富集的苯并呋喃基β硝基醇与对映选择性令人满意（高达98％ee）。使用该催化方案，可以在短时间内方便地制备生物活性（S）-苯并呋喃基β-氨基醇。

  DOI：

  10.1039/c6ob02569b

文献信息

• Falcipain Inhibitors: Optimization Studies of the 2-Pyrimidinecarbonitrile Lead Series
  作者：Jose M. Coterón、David Catterick、Julia Castro、María J. Chaparro、Beatriz Díaz、Esther Fernández、Santiago Ferrer、Francisco J. Gamo、Mariola Gordo、Jiri Gut、Laura de las Heras、Jennifer Legac、Maria Marco、Juan Miguel、Vicente Muñoz、Esther Porras、Juan C. de la Rosa、Jose R. Ruiz、Elena Sandoval、Pilar Ventosa、Philip J. Rosenthal、Jose M. Fiandor

  DOI：10.1021/jm100556b

  日期：2010.8.26

  were studied as potential falcipain inhibitors and therefore potential antiparasitic lead compounds, with the 5-substituted-2-cyanopyrimidine chemical class emerging as the most potent and promising lead series. Through a sequential lead optimization process considering the different positions present in the initial scaffold, nanomolar and subnanomolar inhibitors at falcipains 2 and 3 were identified

  Falcipain-2和falcipain-3是疟原虫恶性疟原虫的木瓜蛋白酶家族半胱氨酸蛋白酶负责宿主血红蛋白水解以提供用于寄生虫蛋白质合成的氨基酸。研究了不同的杂芳基腈衍生物作为潜在的falcipain抑制剂，因此潜在的抗寄生虫铅化合物，其中5-取代的2-氰基嘧啶化学类别成为最有效和有前途的铅系列。考虑到初始支架中存在的不同位置，通过顺序的前导优化过程，鉴定出了在恶性激素2和3处的纳摩尔和亚纳摩尔抑制剂，并具有在微摩尔范围内对抗培养的寄生虫的活性。在铅分子中引入质子化胺后，对培养的寄生虫的活性显着提高了1000倍，而其他SAR趋势没有明显改变。
• An efficient synthesis of benzofuran derivatives under conventional/non-conventional method
  作者：Suryakant B. Sapkal、Kiran F. Shelke、Bapurao B. Shingate、Murlidhar S. Shingare

  DOI：10.1016/j.cclet.2010.06.038

  日期：2010.12

  Abstract 1-Methyl-3-ethyl imidazolium bromide [meim]Br/basic alumina (Al 2 O 3 ) has been found to promote the cyclocondensation of chloroacetone/chloroethyl acetate with salicylaldehydes under conventional as well as microwave irradiation to yield benzofuran derivatives.

  摘要发现1-甲基-3-乙基溴化咪唑鎓[meim] Br /碱性氧化铝（Al 2 O 3）在常规和微波辐射下可促进氯丙酮/氯乙酸乙酯与水杨醛的环缩合反应，生成苯并呋喃衍生物。
• Tandem Synthesis of 2-Carboxybenzofurans <i>via</i> Sequential Cu-Catalyzed C–O Coupling and Mo(CO)₆-Mediated Carbonylation Reactions
  作者：Qinliang Mo、Nan Sun、Liqun Jin、Baoxiang Hu、Zhenlu Shen、Xinquan Hu

  DOI：10.1021/acs.joc.0c01620

  日期：2020.9.4

  A modular tandem synthesis of 2-carboxybenzofurans from 2-gem-dibromovinylphenols has been established based on a sequence of Cu-catalyzed intramolecular C–O coupling and Mo(CO)6-mediated intermolecular carbonylation reactions. This protocol allowed one-step access to a broad variety of functionalized benzofuran-2-carboxylic acids, esters, and amides in good to excellent yields under Pd- and CO gas-free

  由2- 2-羧基苯并呋喃的模块化串联合成宝石-dibromovinylphenols已经基于Cu催化的分子内CO耦合和Mo（CO）的序列被建立6个介导的分子间羰基化反应。该方案允许在无Pd和CO气体条件下以良好至极佳的收率一步一步获得各种官能化的苯并呋喃-2-羧酸，酯和酰胺。
• Aminoalkyl benzofuran derivatives, their production and compositions containing them
  申请人：Merck & Co., Inc.

  公开号：EP0029311B1

  公开（公告）日：1985-01-23
• TRI-ARYL ACID DERIVATIVES AS PPAR RECEPTOR LIGANDS
  申请人：Aventis Pharma Deutschland GmbH

  公开号：EP1177176A1

  公开（公告）日：2002-02-06