2-iodo-3,3-dimethyl-2,3-dihydro-1H-benzo[f]chromene | 1617544-65-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 2-iodo-3,3-dimethyl-2,3-dihydro-1H-benzo[f]chromene
• CAS: 1617544-65-6
• 化学式: C₁₅H₁₅IO
• 分子量: 338.188
• InChiKey: VSVFVVRBQVKFPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  异戊烯醇 、 2-萘酚 在 碘 作用下， 以 氯仿 为溶剂， 反应 1.3h， 以31%的产率得到2-iodo-3,3-dimethyl-2,3-dihydro-1H-benzo[f]chromene
  参考文献：
  名称：

  Molecular iodine catalyst promoted synthesis of chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling

  摘要：

  Molecular iodine as an inexpensive catalyst is described in the construction of 2-substituted or 2,2-disubstituted chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling. For the synthesis of chromans, phenols and allylic alcohols were refluxed in chloroform in presence of 20 mol % I-2 while [3+3] cyclocoupling of phenols and cinnamic acids proceeded to give 4-aryl-3,4-dihydrobenzopyran-2-ones using 30 mol % I-2. Later reaction occurs via a tandem hydroarylation-esterification process at 120-130 degrees C under solvent free conditions. Chromans were obtained in 20-92% yields and substituted 4-aryl-3,4-dihydrobenzopyran-2-ones were obtained in 5-85% yields. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.093