3-(4-nitrophenylmethyl)isobenzofuran-1(3H)-one | 85164-40-5

• 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: 3-(4-nitrophenylmethyl)isobenzofuran-1(3H)-one
• 英文别名: 3-(4-nitrobenzyl)phthalide；3-(4-nitrobenzyl)isobenzofuran-1(3H)-one；p-Nitro-benzylphthalid；3-<4-Nitro-benzyl>-phthalid；3-(4-nitro-benzyl)-3H-isobenzofuran-1-one；3-[(4-nitrophenyl)methyl]-3H-2-benzofuran-1-one
• CAS: 85164-40-5
• 化学式: C₁₅H₁₁NO₄
• 分子量: 269.257
• InChiKey: SIYFCXOVKAEFCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-硝基苯乙烯 在 2-均三甲苯基-2,5,6,7-四氢吡咯并[2,1-C][1,2,4]三唑-4-鎓氯化物 、 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 甲苯 为溶剂， 反应 7.0h， 生成 3-(4-nitrophenylmethyl)isobenzofuran-1(3H)-one
  参考文献：
  名称：

  NHC-catalyzed oxidative cyclization reaction for the synthesis of 3-substituted phthalides

  摘要：

  一种高效的NHC催化的2-烯基苯甲醛的多米诺氧化/氧杂Michael加成反应已经开发出来，可以提供具有广泛底物范围和广泛功能基团耐受性的带有C3立体异构中心的3-取代邻苯二甲酸酐。

  DOI：

  10.1039/c3ob42546k

文献信息

• Synthesis of 3-Benzylphthalide Derivatives by Using a TDAE Strategy
  作者：Patrice Vanelle、Maroua Ibrahimi、Omar Khoumeri、Raoudha Abderrahim、Thierry Terme

  DOI：10.1055/a-1290-8349

  日期：2021.2

  A one-pot synthesis of new 3-benzylphthalide derivatives was developed by using a strategy based on tetrakis(dimethylamino)ethylene (TDAE). The reactions in the presence of TDAE of substituted benzyl chlorides with methyl 2-formylbenzoate or of substituted methyl-2-formylbenzoates with 4-nitrobenzyl chloride furnished the corresponding isobenzofuran-1(3H)-one products in moderate to good yields.

  使用基于四（二甲氨基）乙烯 (TDAE) 的策略开发了新型 3-苄基苯酞衍生物的一锅法合成。在 TDAE 存在下，取代苄基氯与 2-甲酰基苯甲酸甲酯或取代 2-甲酰基苯甲酸甲酯与 4-硝基苄基氯的反应以中等至良好的产率提供相应的异苯并呋喃-1(3H)-酮产物。
• Expeditious synthesis of 3,4-dihydroisocoumarins and phthalides using the Heck–Matsuda reaction
  作者：Eduardo T. da Penha、José Augusto Forni、André F.P. Biajoli、Carlos Roque D. Correia

  DOI：10.1016/j.tetlet.2011.09.014

  日期：2011.11

  Several 3,4-dihydroisocoumarins and phthalides were synthesized by an effective Heck-Matsuda reaction involving an ortho carboxybenzenediazonium salt with a series of styrenes bearing electron donating and electron withdrawing groups, methylvinyl ketone, and methyl acrylate. The reaction was carried out in an open-flask with 1% mol of palladium acetate in aqueous ethanol at similar to 80 degrees C, giving the correspondent 3-aryl-3,4-dihydroisocoumarins and phthalides with good overall yields. The electronic nature of the group attached to the olefin is a key feature for the regioselectivity of the cyclization step. (C) 2011 Elsevier Ltd. All rights reserved.
• Bellinger, Geoffrey C. A.; Campbell, William E.; Giles, Robin G. F., Journal of the Chemical Society. Perkin transactions I, 1982, # 12, p. 2819 - 2826
  作者：Bellinger, Geoffrey C. A.、Campbell, William E.、Giles, Robin G. F.、Tobias, Julius D.

  DOI：——

  日期：——
• BELLINGER, G. C. A.;CAMPBELL, W. E.;GILES, R. G. F.;TOBIAS, J. D., J. CHEM. SOC. PERKIN TRANS., 1982, N 12, 2819-2825
  作者：BELLINGER, G. C. A.、CAMPBELL, W. E.、GILES, R. G. F.、TOBIAS, J. D.

  DOI：——

  日期：——