(Z)-1-butyl-3-iodophenylmethylene-1,3-dihydroisobenzofuran | 1205555-77-6

• 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-butyl-3-iodophenylmethylene-1,3-dihydroisobenzofuran
• 英文别名: (3Z)-1-butyl-3-[iodo(phenyl)methylidene]-1H-2-benzofuran
• CAS: 1205555-77-6
• 化学式: C₁₉H₁₉IO
• 分子量: 390.264
• InChiKey: RJGQWPJPWFLNMN-HNENSFHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(2-(phenylethynyl)phenyl)pentan-1-ol 在 碘 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 15.0h， 生成 1-butyl-4-iodo-3-phenyl-1H-isochromene 、 (Z)-1-butyl-3-iodophenylmethylene-1,3-dihydroisobenzofuran
  参考文献：
  名称：

  A Simple and Mild Synthesis of 1H-Isochromenes and (Z)-1-Alkylidene-1,3-dihydroisobenzofurans by the Iodocyclization of 2-(1-Alkynyl)benzylic Alcohols

  摘要：

  A variety of iodo-substituted isochromenes, dihydroisobenzofurans, and pyranopyridines are readily prepared in good to excellent yields under mild conditions by the iodocyclization of readily available 2-(1-alkynyl)benzylic alcohols or 2-(1-alkynyl)-3-(hydroxymethyl)pyridines. Reactions are carried out in MeCN at 25 degrees C with 3 equiv of I-2 as the iodine source and NaHCO3 (3 equiv) as the base. The regiochemical outcome of the reaction strongly depends on the substitution pattern of the starting material. In particular, the 5-exo-dig cyclization mode, leading to dihydroisobenzofurans, is observed in the case of substrates bearing a tertiary alcoholic group, owing to the gem-dialkyl effect, while the 6-endo-dig cyclization mode, leading to isochromene or pyranopyridines, is the usually preferred pathway in the case of substrates bearing a primary or secondary alcoholic group.

  DOI：

  10.1021/jo902333y