(Z)-1-benzylidene-3-methoxy-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: (Z)-1-benzylidene-3-methoxy-1,3-dihydroisobenzofuran
• 英文别名: 3-methoxy-1-(phenylmethylene)-3-hydroisobenzofuran；(3Z)-3-benzylidene-1-methoxy-1H-2-benzofuran
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: UDSJBEWWLRLXMI-PTNGSMBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-碘苄醇 在 四(三苯基膦)钯 copper(l) iodide 、 potassium carbonate 、 正丁胺 、 pyridinium chlorochromate 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 (Z)-1-benzylidene-3-methoxy-1,3-dihydroisobenzofuran
  参考文献：
  名称：

  钯催化的 2-炔基苯甲醛与芳基碘在甲醇中的酯化-氢芳基化反应

  摘要：

  在 Pd(PPh 3 ) 4 和 K 2 CO 3 存在下，2-炔基苯甲醛与芳基碘在甲醇回流下反应 24 小时，得到脱氢加成产物，即 2-(2,2-二取代-乙烯基)苯甲酸甲酯收益率适中；与环化产物一起，3-甲氧基-1-单取代-亚甲基-3-氢异苯并呋喃的产率为 3-18%。

  DOI：

  10.1055/s-2004-829056

文献信息

• Selective Base-Promoted Synthesis of Dihydroisobenzofurans by Domino Addition/Annulation Reactions of ortho-Alkynylbenzaldehydes
  作者：Giorgio Abbiati、Monica Dell’Acqua、Diego Facoetti、Elisabetta Rossi

  DOI：10.1055/s-0029-1218766

  日期：2010.7

  nucleophilic addition/annulation reaction of ortho-alkynylbenzaldehydes in the presence of methanol. The reactions of aryl-, trimethylsilyl- and diethoxymethyl-substituted alkynylbenzaldehydes occurred with complete regio­selectivity in good to excellent yields under microwave irradiation. The reactions of alkyl-substituted alkynylbenzaldehydes took place with good yields and high regioselectivity only when

  二氢异苯并呋喃核的合成是通过在甲醇存在下，由邻炔基苯甲醛进行碱促进的串联亲核加成/环化反应实现的。在微波辐射下，芳基，三甲基甲硅烷基和二乙氧基甲基取代的炔基苯甲醛的反应具有完全的区域选择性，产率高至优异。仅当在室温下且在催化量的金（III）盐存在下进行时，烷基取代的炔基苯甲醛的反应才以高收率和高区域选择性进行。讨论了可能的反应机理。暂时合理地说明了炔基末端的取代基对环化模式的影响。 炔烃-杂环-多米诺反应-微波促进的合成-金
• Silver versus Gold Catalysis in Tandem Reactions of Carbonyl Functions onto Alkynes: A Versatile Access to Furoquinoline and Pyranoquinoline Cores
  作者：Thomas Godet、Carine Vaxelaire、Carine Michel、Anne Milet、Philippe Belmont

  DOI：10.1002/chem.200700202

  日期：2007.6.25

  An efficient and versatile tandem process of acetalization and cycloisomerization reactions has been developed for the reactions of 1-alkynyl-2-carbonylquinoline substrates. The reaction occurs thanks to Au(I) and Ag(I) catalysis. Silver(I) catalysis has been extensively studied (11 different silver species) on a broad range of quinoline derivatives (variation of alkyne substituent, of carbonyl function

  对于1-炔基-2-羰基喹啉底物的反应，已经开发出一种高效且通用的串联缩醛化和环异构化反应的方法。该反应由于Au（I）和Ag（I）催化而发生。已经对广泛的喹啉衍生物（炔烃取代基，羰基官能团和亲核试剂的变化）进行了广泛的研究（11种不同的银种类），研究了银（I）催化作用，从而产生了各种呋喃喹啉和吡喃喹啉部分。对推测的机理以及DFT-B3 LYP / 6-31G **计算给出了见解，以解决所观察到的6-内和5-外区域选择性。
• 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
• Palladium-Catalyzed Esterification-Hydroarylation Reactions of 2-Alkynylbenzaldehydes with Aryl Iodides in Methanol
  作者：Ming-Jung Wu、Li-Lan Wei、Li-Mei Wei、Wen-Bin Pan

  DOI：10.1055/s-2004-829056

  日期：——

  The reaction of 2-alkynylbenzaldehydes with aryl iodides in the presence of Pd(PPh 3 ) 4 and K 2 CO 3 in refluxing methanol for 24 hours gave the dehydrogenation-addition products, methyl 2-(2,2-disubstituted-vinyl)benzoates in modest yields; together with the cyclization products, 3-methoxy-1-monosubstituted-methylene-3-hydroisobenzofurans in 3-18% yields.

  在 Pd(PPh 3 ) 4 和 K 2 CO 3 存在下，2-炔基苯甲醛与芳基碘在甲醇回流下反应 24 小时，得到脱氢加成产物，即 2-(2,2-二取代-乙烯基)苯甲酸甲酯收益率适中；与环化产物一起，3-甲氧基-1-单取代-亚甲基-3-氢异苯并呋喃的产率为 3-18%。