(Z)-1-benzylidene-5-fluoro-3-methoxy-1,3-dihydroisobenzofuran | 1273420-50-0

• 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-5-fluoro-3-methoxy-1,3-dihydroisobenzofuran
• 英文别名: (3Z)-3-benzylidene-6-fluoro-1-methoxy-1H-2-benzofuran
• CAS: 1273420-50-0
• 化学式: C₁₆H₁₃FO₂
• 分子量: 256.276
• InChiKey: RVRWWZDZRKCCCC-DHDCSXOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 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：
  3

反应信息

• 作为产物：
  描述：

  甲醇 、 2-溴-5-氟苯甲醛 、 苯乙炔 在 bis({5-chloro-2-[(4-chlorophenyl)(hydroxyimino)methyl]phenyl})cyclodipalladachl-orane-1,3,4-tris(ylium)-2-uide 、 potassium hydroxide 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 反应 0.25h， 以72%的产率得到(Z)-1-benzylidene-5-fluoro-3-methoxy-1,3-dihydroisobenzofuran
  参考文献：
  名称：

  Dihydroisobenzofurans的合成通过钯催化顺序炔基/微波辐射下2-溴苄基和2-氯苄基醇的环

  摘要：

  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

  DOI：

  10.1002/adsc.201400457

文献信息

• From domino to multicomponent: synthesis of dihydroisobenzofurans
  作者：Monica Dell’Acqua、Diego Facoetti、Giorgio Abbiati、Elisabetta Rossi

  DOI：10.1016/j.tet.2010.12.056

  日期：2011.2

  A variety of substituted dihydroisobenzofurans can be easily synthesized in high yields by a one-pot three-component approach starting from o-bromoarylaldehydes, methanol, and terminal alkynes. The reaction occurs through an unprecedented cooperative palladium/base promoted coupling/addition/cyclization sequence. (C) 2010 Elsevier Ltd. All rights reserved.
• 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