(Z)-1-(4-methylbenzylidene)-1,3-dihydroisobenzofuran | 1246831-55-9

• 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: (Z)-1-(4-methylbenzylidene)-1,3-dihydroisobenzofuran
• 英文别名: (z)-1-(4-Methyl-benzylidene)-1,3-dihydro-isobenzofuran；(3Z)-3-[(4-methylphenyl)methylidene]-1H-2-benzofuran
• CAS: 1246831-55-9
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: JWUKFZMHQGSDLS-YBEGLDIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-1-(4-methylbenzylidene)-1,3-dihydroisobenzofuran 、 对二甲氨基苯甲醛 在 18-冠醚-6 、 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以86%的产率得到N,N-dimethyl-4-((Z)-((Z)-3-(4-methylbenzylidene)isobenzofuran-1(3H)-ylidene)methyl)aniline
  参考文献：
  名称：

  A concise synthesis of tunable fluorescent 1,3-dihydroisobenzofuran derivatives as new fluorophores

  摘要：

  A convenient Potassium tert-butoxide catalyzed addition elimination reaction has been achieved using exo-cyclic end l ethers and aryl aldehydes as the starting materials. The transition-metal free reaction proceeded smoothly to afford 1,3-dihydroisobenzofuran derivatives with good to excellent yields. More importantly, the resulting products were discovered as novel fluorophores with good fluorescence properties and remarkable Stokes shifts. Changing the nature of the substituents in 1,3-dihydroisobenzofurans derivatives allowed the maximum emission wavelengths to be tuned between 438 and 597 nm and the Stokes shifts varied between 63 and 166 nm. In particular, derivative C27 containing a piperidyl and a cyano group showed the maximum emission wavelength of 597 nm and a Stokes shift of 166 nm. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2014.10.013
• 作为产物：
  描述：

  2-[ 2 -(4-甲基苯基)乙炔基]苯甲醛 在 sodium tetrahydroborate 、 caesium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.33h， 生成 (Z)-1-(4-methylbenzylidene)-1,3-dihydroisobenzofuran
  参考文献：
  名称：

  Regio- and stereoselective intramolecular hydroalkoxylation of aromatic alkynols: an access to dihydroisobenzofurans under transition-metal-free conditions

  摘要：

  一种高效的无过渡金属合成二氢异苯并呋喃衍生物的方法已被开发，该方法通过介导铯碳酸盐对芳香族炔醇进行分子内氢烷氧化反应。反应以区位选择性进行，专一生成5-exo-dig产物，并且仅观察到新生成双键的Z-异构体。该新方法具有反应条件温和、操作便捷和选择性满意的特点。

  DOI：

  10.1007/s11696-020-01159-5

文献信息

• Solvent-Switched Benzylic Methylene Functionalization: Addition, Ring-Opening, Cyclization, and Unexpected Cleavage of C–O and C–C Bonds
  作者：Deng Yuan Li、Xue Song Shang、Guo Rong Chen、Pei Nian Liu

  DOI：10.1021/ol401470y

  日期：2013.8.2

  been achieved using imines as reagents and potassium tert-butoxide as the catalyst. Depending on the solvent used, the reaction proceeds by two pathways. In THF, an addition/elimination reaction of exo-cyclic enol ethers with imines provides dihydroisobenzofuran derivatives in good yield. In DMSO, an addition/ring-opening/cyclization cascade reaction occurs with unexpected cleavage of C–O and C–C bonds

  使用亚胺作为试剂并使用叔丁醇钾作为催化剂，可以实现环外烯醇醚的分子间苄基亚甲基官能化。根据所使用的溶剂，反应通过两个途径进行。在THF中，的加成/消除反应外切-环烯醇醚与亚胺提供以良好的收率二氢异苯并呋喃衍生物。在DMSO中，加成/开环/环化级联反应会发生意外的C–O和C–C键断裂，从而在环境反应条件下以高收率提供异喹啉-1（2 H）-一产品。
• 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。
• Selective cyclization of alkynols and alkynylamines catalyzed by potassium tert-butoxide
  作者：Deng Yuan Li、Ke Ji Shi、Xiao Feng Mao、Zheng Le Zhao、Xin Yan Wu、Pei Nian Liu

  DOI：10.1016/j.tet.2014.06.078

  日期：2014.9
• Synthesis of Dihydroisobenzofurans<i>via</i>Palladium-Catalyzed Sequential Alkynylation/Annulation of 2-Bromobenzyl and 2-Chlorobenzyl Alcohols under Microwave Irradiation
  作者：Eduardo Buxaderas、Diego A. Alonso、Carmen Nájera

  DOI：10.1002/adsc.201400457

  日期：2014.11.3

  AbstractThe palladium‐catalyzed synthesis of dihydroisobenzofurans has been performed by sequential Sonogashira cross‐coupling/cyclization reactions between terminal alkynes and 2‐(hydroxymethyl)bromo‐ and chlorobenzenes in methanol as solvent at 130 °C under microwave irradiation. A 4,4′‐dichlorobenzophenone oxime‐derived chloro‐bridged palladacycle is an efficient pre‐catalyst to perform this tandem process using 2‐dicyclohexylphosphanyl‐2′,4′,6′‐triisopropylbiphenyl (Xphos) as ancillary ligand and potassium hydroxide as base in the absence of a copper cocatalyst. Under these conditions, functionalized 2‐bromo‐ and 2‐chlorobenzaldehydes are also suitable partners in the domino process affording phthalans in good yields. All the reactions can be performed under air and employing reagent‐grade chemicals under low loading conditions (1 mol% Pd).magnified image