2-(1H-2-Benzopyran-3-yl)benzaldehyde | 166757-13-7

• 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: 2-(1H-2-Benzopyran-3-yl)benzaldehyde
• 英文别名: 2-(1H-isochromen-3-yl)benzaldehyde
• CAS: 166757-13-7
• 化学式: C₁₆H₁₂O₂
• 分子量: 236.27
• InChiKey: ANALZYSTYGFNCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1H-2-Benzopyran-3-yl)benzaldehyde 在 盐酸 作用下， 生成
  参考文献：
  名称：

  Intramolecular Addition to an Unactivated Carbon-Carbon Triple Bond via an Apparent 6-Endo Digonal Pathway

  摘要：

  DOI：

  10.1016/00404-0399(50)0891f-
• 作为产物：
  描述：

  2,2'-(ethyne-1,2-diyl)dibenzaldehyde 在 二氢吡啶 作用下， 以 甲苯 为溶剂， 以25%的产率得到2-(1H-2-Benzopyran-3-yl)benzaldehyde
  参考文献：
  名称：

  黄金催化的1 H-异色酮的反应发展和机理研究

  摘要：

  邻位金催化的多米诺环化/亲核反应已经研究了-羰基炔基芳基。因此，已选择2-（吡啶-2-基乙炔基）苯甲醛来分离可能参与反应机理的关键中间体。利用汉茨sch酯（HEH）作为亲核试剂，不可能分离出相应的金-烯基物种。然而，当甲醇用作溶剂（和亲核试剂）时，预期的螯合金-乙烯基络合物被分离出来，并通过X射线分析明确鉴定。当乙醇反应混合物中存在HEH时，同位素研究表明，金-乙烯基络合物的Au-C键的裂解是通过原金属化途径进行的，而不是通过合理的金属-氢化物还原消除机理进行的。最后，为了扩大先前报道的环化/还原反应的范围，

  DOI：

  10.1021/acscatal.6b02636

文献信息

• An Unusual Example of a 6-Endo-Dig Addition to an Unactivated Carbon-Carbon Triple Bond
  作者：Albert Padwa、Keith E. Krumpe、M. David Weingarten

  DOI：10.1021/jo00122a047

  日期：1995.9

  Methyl 2-[2-[2-(1-hydroxy-1-ethyl)phenyl]ethynyl]benzoate was prepared as an intermediate for subsequent conversion to an a-diazo ketone. Under the basic conditions used to hydrolyze the methyl ester, the neighboring hydroxyl functionality underwent reaction with the unactivated acetylenic group, producing a benzopyranyl-substituted alpha-diazoacetophenone. Treatment of this diazocarbonyl compound with a catalytic quantity of rhodium(II) mandelate afforded a novel dibenzo[a,e]cyclononenone derivative. The reaction proceeds via an initially formed oxonium ylide which rearranges further by means of a 1,2-alkyl shift. A prime factor in determining the direction of internal cyclization to the triple bond is the presence of the carbomethoxy group in the ortho position of the beta-phenyl ring. Thus, in contrast with related systems which exhibit a clear preference for 5-exo-dig cyclization at the acetylenic center, the 6-endo-dig addition is the preferred pathway for the o-formyl- and o-carbomethoxy-substituted alkynyl alcohols. Careful monitoring of the reaction actually showed that the reaction proceeds by initial formation of the 5-exo-dig product followed by a novel rearrangement to the 6-endo product.
• Gold-Catalyzed Access to 1<i>H</i>-Isochromenes: Reaction Development and Mechanistic Insight
  作者：Eder Tomás-Mendivil、Clément F. Heinrich、Jean-Claude Ortuno、Jérôme Starck、Véronique Michelet

  DOI：10.1021/acscatal.6b02636

  日期：2017.1.6

  take part in the reaction mechanism. Employing Hantzsch ester (HEH) as nucleophile, it has been impossible to isolate the corresponding gold–alkenyl specie; however, when methanol was used as solvent (and nucleophile), the expected chelate gold–vinyl complex was isolated and unambiguously characterized by X-ray analysis. When HEH is present in the alcoholic reaction mixture, isotopic studies show that

  邻位金催化的多米诺环化/亲核反应已经研究了-羰基炔基芳基。因此，已选择2-（吡啶-2-基乙炔基）苯甲醛来分离可能参与反应机理的关键中间体。利用汉茨sch酯（HEH）作为亲核试剂，不可能分离出相应的金-烯基物种。然而，当甲醇用作溶剂（和亲核试剂）时，预期的螯合金-乙烯基络合物被分离出来，并通过X射线分析明确鉴定。当乙醇反应混合物中存在HEH时，同位素研究表明，金-乙烯基络合物的Au-C键的裂解是通过原金属化途径进行的，而不是通过合理的金属-氢化物还原消除机理进行的。最后，为了扩大先前报道的环化/还原反应的范围，
• Intramolecular Addition to an Unactivated Carbon-Carbon Triple Bond via an Apparent 6-Endo Digonal Pathway
  作者：M Weingarten

  DOI：10.1016/00404-0399(50)0891f-

  日期：1995.7.3