1-(pyrazinylmethylidene)-1,3-dihydroisobenzofuran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 1-(pyrazinylmethylidene)-1,3-dihydroisobenzofuran
• 英文别名: (Z)-2-(3H-isobenzofuran-1ylidenemethyl)-pyrazine；2-[(Z)-3H-2-benzofuran-1-ylidenemethyl]pyrazine
• 化学式: C₁₃H₁₀N₂O
• 分子量: 210.235
• InChiKey: QNAHGIVJBIYHNU-QPEQYQDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-碘苄醇 在 四(三苯基膦)钯 copper(l) iodide 、 sodium 、 正丁胺 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 22.0h， 生成 1-(pyrazinylmethylidene)-1,3-dihydroisobenzofuran
  参考文献：
  名称：

  Substituent effect on anionic cycloaromatization of 2-(2-substituted ethynyl)benzonitriles and related molecules

  摘要：

  Mothanolysis of 2-(2-substituted ethynyl)benzonitriles based on the nature of substituents gave 5-exo product, isoindolones and 6-endo product, isoquinolones, respectively. When a bulky substituent, such as tert-butyl group, was employed in this cyclization reaction, a 5-exo adduct was obtained. Phenyl and thienyl groups which can stabilize the alpha-anion affect the cyclization reaction to produce the 5-exo adducts. Pyridinyl and pyrazinyl groups can also stabilize the a-anion, but the formation of a more stable intermediate by coordination of sodium with nitrogen atom leads to the 6-endo products. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00753-6

文献信息

• Regioselective synthesis of phthalans via Cu(OTf)2-catalyzed 5-exo-dig intramolecular hydroalkoxylation of 2-(ethynyl)benzyl alcohols
  作者：Chandrasekaran Praveen、Chandran Iyyappan、Paramasivan Thirumalai Perumal

  DOI：10.1016/j.tetlet.2010.07.030

  日期：2010.9

  efficient, regioselective Cu(OTf)2-catalyzed 5-exo-dig intramolecular hydroalkoxylation of 2-(ethynyl)benzyl alcohol, which provides a concise access to functionalized phthalan in high yields has been developed. A wide range of substrates possessing terminal, internal, and heteroaromatic alkynes can be efficiently transformed into the targeted phthalans. Substrates with primary, secondary, and tertiary benzyl

  一种高效，区域选择性的Cu（OTF）2催化的5-外型-挖2-（乙炔基）苄醇，它提供一个简明的访问以高收率官能phthalan的分子内hydroalkoxylation已经研制成功。具有末端，内部和杂芳族炔烃的多种底物可以有效地转化为目标邻苯二甲酸酯。具有伯，仲和叔苄醇的底物也进展良好，以高收率生产了相应的邻苯二甲酸酯。不论底物的性质如何，当区域选择性成为一个问题时，环化反应都遵循高度选择性的5- exo - dig区域化学。
• Regioselective synthesis and evaluation of 3-alkylidene-1, 3-dihydroisobenzofurans as potential antidepressant agents
  作者：C PRAVEEN、C IYYAPPAN、K GIRIJA、K SURESH KUMAR、P T PERUMAL

  DOI：10.1007/s12039-011-0150-z

  日期：2012.3

  3-Alkylidene-1,3-dihydroisobenzofurans exhibited moderate antidepressant activity as evaluated by forced swim and tail suspension test methods. Virtual screening was carried out by docking the designed compounds into the serotonin binding sites of arabinase protein to predict the analogue binding mode of the compounds to the SSRIs.

  3-亚烷基-1,3-二氢异苯并呋喃在强迫游泳和尾悬试验方法的评估中表现出中等程度的抗抑郁活性。通过将设计的化合物与阿拉伯蛋白酶的血清素结合位点对接，进行了虚拟筛选，以预测化合物与 SSRIs 的类似结合模式。
• Substituent effect on anionic cycloaromatization of 2-(2-substituted ethynyl)benzonitriles and related molecules
  作者：Wen-Der Lu、Chi-Fong Lin、Chyi-Jia Wang、Shih-Jen Wang、Ming-Jung Wu

  DOI：10.1016/s0040-4020(02)00753-6

  日期：2002.9

  Mothanolysis of 2-(2-substituted ethynyl)benzonitriles based on the nature of substituents gave 5-exo product, isoindolones and 6-endo product, isoquinolones, respectively. When a bulky substituent, such as tert-butyl group, was employed in this cyclization reaction, a 5-exo adduct was obtained. Phenyl and thienyl groups which can stabilize the alpha-anion affect the cyclization reaction to produce the 5-exo adducts. Pyridinyl and pyrazinyl groups can also stabilize the a-anion, but the formation of a more stable intermediate by coordination of sodium with nitrogen atom leads to the 6-endo products. (C) 2002 Elsevier Science Ltd. All rights reserved.