Dihydrobenzo[b]furan-2-carbonitrile | 24889-97-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: Dihydrobenzo[b]furan-2-carbonitrile
• 英文别名: 2-cyano-2,3-dihydrobenzofuran；2,3-Dihydro-2-benzofurancarbonitrile；2,3-dihydro-1-benzofuran-2-carbonitrile
• CAS: 24889-97-2
• 化学式: C₉H₇NO
• 分子量: 145.161
• InChiKey: SHQUPDNGGXRYRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Dihydrobenzo[b]furan-2-carbonitrile 在 三氯化铝 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 6.25h， 生成 2-(5-acetyl-2,3-dihydro-2-benzofuranyl)-2-imidazoline
  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paper describes a number of analogues of this ring system, including compounds in which one of the oxygen atoms has been replaced by a methylene group and also those in which the ring size has been changed to give, for example, furan and thiophene derivatives.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：

  苯并二氢呋喃-2-羧酸 在 吡啶 、 ammonium hydroxide 、 氯化亚砜 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 2.92h， 生成 Dihydrobenzo[b]furan-2-carbonitrile
  参考文献：
  名称：

  I3咪唑啉受体拮抗剂KU14R及相关2,3-二氢苯并[b]呋喃衍生物的制备

  摘要：

  本文介绍了一系列新型咪唑啉胰岛素分泌剂依法罗生类似物（包括 I3 受体拮抗剂 KU14R）的制备和表征。在胰岛素分泌研究中，用选定的官能团取代依法罗生的咪唑啉环会导致其失去活性或产生极弱的 I3 受体拮抗剂活性。研究发现，咪唑类似物 KU14R 在该试验中是一种 I3-拮抗剂，可作为一种有用的生物学工具。

  DOI：

  10.1055/s-2001-16079

文献信息

• Iridium-Catalyzed Hydrogen Transfer: Synthesis of Substituted Benzofurans, Benzothiophenes, and Indoles from Benzyl Alcohols
  作者：Bruno Anxionnat、Domingo Gomez Pardo、Gino Ricci、Kai Rossen、Janine Cossy

  DOI：10.1021/ol401610e

  日期：2013.8.2

  An iridium-catalyzed hydrogen transfer has been developed in the presence of p-benzoquinone, allowing the synthesis of a diversity of substituted benzofurans, benzothiophenes, and indoles from substituted benzylic alcohols.

  在对苯醌的存在下已经开发出铱催化的氢转移，从而可以由取代的苯甲醇合成各种取代的苯并呋喃，苯并噻吩和吲哚。
• .alpha.-Adrenoceptor reagents. 2. Effects of modification of the 1,4-benzodioxan ring system on .alpha.-adrenoreceptor activity
  作者：Christopher B. Chapleo、Peter L. Myers、Richard C. M. Butler、John A. Davis、John C. Doxey、Stanley D. Higgins、Malcolm Myers、Alan G. Roach、Colin F. C. Smith

  DOI：10.1021/jm00371a003

  日期：1984.5

  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.
• Preparation of the I₃ Imidazoline Receptor Antagonist KU14R and Related 2,3-Dihydrobenzo[<b><i>b</i></b>]furan Derivatives
  作者：Christopher Ramsden、J. Clews、Noel Morgan

  DOI：10.1055/s-2001-16079

  日期：——

  The preparation and characterisation of a series of novel analogues of the imidazoline insulin secretagogue efaroxan, including the I3-receptor antagonist KU14R, are described. Replacement of the imidazoline ring of efaroxan by selected functional groups leads either to loss of activity or to very weak I3-agonist activity in insulin secretion studies. The imidazole analogue KU14R was found to be an I3-antagonist in this assay and useful as a biological tool.

  本文介绍了一系列新型咪唑啉胰岛素分泌剂依法罗生类似物（包括 I3 受体拮抗剂 KU14R）的制备和表征。在胰岛素分泌研究中，用选定的官能团取代依法罗生的咪唑啉环会导致其失去活性或产生极弱的 I3 受体拮抗剂活性。研究发现，咪唑类似物 KU14R 在该试验中是一种 I3-拮抗剂，可作为一种有用的生物学工具。

表征谱图