1-isopropoxy-3-propyl-1H-isochromene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1-isopropoxy-3-propyl-1H-isochromene
• 英文别名: 1-propan-2-yloxy-3-propyl-1H-isochromene
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: AFKPBXHHQFCLJY-UHFFFAOYSA-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：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  邻溴苯甲醛 在 trans-bis(triphenylphosphine)palladium dichloride 、 C₃₂H₃₆AgN₄O₄S₂⁽¹⁺⁾*BF₄^(1-) 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 1.17h， 生成 1-isopropoxy-3-propyl-1H-isochromene
  参考文献：
  名称：

  Mild Regiospecific Synthesis of 1-Alkoxy-isochromenes Catalyzed by Well-Defined [Silver(I)(Pyridine-Containing Ligand)] Complexes

  摘要：

  The synthesis of 3-substituted-1-alkoxyisochromenes starting from 2-alkynylbenzaldehydes and different alcohols is reported. The reaction is catalyzed by a silver(1) complex with an original macrocyclic pyridine-containing ligand. The approach is characterized by absolute regioselectivity, mild reaction conditions, good to excellent reaction yields, cleanness of the reaction, and reduced purification steps. The reaction mechanism was investigated by in-depth H-1 NMR experiments and an aimed "trapping" experiment.

  DOI：

  10.1021/jo5002559

文献信息

• Synthesis of Cyclic Alkenyl Ethers via Intramolecular Cyclization of <i>O</i>-Alkynylbenzaldehydes. Importance of Combination between CuI Catalyst and DMF
  作者：Nitin T. Patil、Yoshinori Yamamoto

  DOI：10.1021/jo049416b

  日期：2004.7.1

  remarkably general method for the synthesis of cyclic alkenyl ethers via the Cu(I)-catalyzed intramolecular cyclization of O-alkynylbenzaldehydes has been developed. The survey of metal catalysts and solvents revealed that the combination of copper(I) iodide and DMF was the catalytic system of choice. The reaction most probably proceeds via the nucleophilic addition of alcohols 2 to O-alkynylbenzaldehydes

  已经开发了一种通过Cu（I）催化的O-炔基苯甲醛的分子内环化反应合成环状烯基醚的有效且非常通用的方法。对金属催化剂和溶剂的调查显示，碘化铜（I）和DMF的组合是选择的催化体系。该反应很可能是通过将醇2亲核加成到O-炔基苯甲醛1上来生成相应的半缩醛，随后半缩醛氧对铜配位炔烃的亲核攻击将得到环状产物3。在所有情况下，反应均以区域特异性方式进行，通过6- endo - dig环化反应生成六元内环产物。
• Mild Regiospecific Synthesis of 1-Alkoxy-isochromenes Catalyzed by Well-Defined [Silver(I)(Pyridine-Containing Ligand)] Complexes
  作者：Monica Dell’Acqua、Brunilde Castano、Clara Cecchini、Tommaso Pedrazzini、Valentina Pirovano、Elisabetta Rossi、Alessandro Caselli、Giorgio Abbiati

  DOI：10.1021/jo5002559

  日期：2014.4.18

  The synthesis of 3-substituted-1-alkoxyisochromenes starting from 2-alkynylbenzaldehydes and different alcohols is reported. The reaction is catalyzed by a silver(1) complex with an original macrocyclic pyridine-containing ligand. The approach is characterized by absolute regioselectivity, mild reaction conditions, good to excellent reaction yields, cleanness of the reaction, and reduced purification steps. The reaction mechanism was investigated by in-depth H-1 NMR experiments and an aimed "trapping" experiment.