3-benzoyl-2-(p-chlorophenyl)tetrahydrofuran | 848785-33-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-benzoyl-2-(p-chlorophenyl)tetrahydrofuran
• 英文别名: [2-(4-chlorophenyl)-tetrahydrofuran-3-yl]phenylmethanone；[2-(4-Chlorophenyl)oxolan-3-yl]-phenylmethanone
• CAS: 848785-33-1
• 化学式: C₁₇H₁₅ClO₂
• 分子量: 286.758
• InChiKey: OTELXXMXKQNWDD-UHFFFAOYSA-N

物化性质

• 沸点：
  427.6±45.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氯苯甲醛 、 4-氯苯丁酮 在 六甲基磷酰三胺 、 Bu₃SnN(Ph)C(OMe)=NPh 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 3-benzoyl-2-(p-chlorophenyl)tetrahydrofuran
  参考文献：
  名称：

  A Novel Darzens type reaction promoted by tributylstannylcarbamate

  摘要：

  Stannylcarbamate 1 proved to be a selective agent for generating organotin(IV) enolates from alpha-halo ketones. Thus, a Darzens reaction was achieved under mild and neutral conditions. The reaction took place without any side reactions and even with aliphatic alpha-halo ketones bearing enolizable alpha'-hydrogens. Various types of alpha,beta-epoxy ketones and esters were obtained in this one-pot reaction. The stereoselectivity of the reaction was influenced by changing the halogen substituent of the alpha-halo ketones and by additives. Moreover, the present method could be applied to gamma- and delta-halo ketones as enolate precursors, and five- and six-membered cyclic compounds were obtained.

  DOI：

  10.1021/jo00051a043

文献信息

• Lewis acid mediated reactions of cyclopropyl aryl ketones with arylaldehydes, facile preparation of 2-(2-hydroxyethyl)-1,3-diarylpropenones
  作者：Min Shi、Yong-Hua Yang、Bo Xu

  DOI：10.1016/j.tet.2004.12.028

  日期：2005.2

  In the presence of Lewis acid TMSOTf, ring-opening reaction of aryl cyclopropyl ketone with arylaldehyde took place under mild conditions to give 2-(2-hydroxyethyl)-1,3-diarylpropenone in good yield. By protection of hydroxy group with triethylsilyl group (TES), the corresponding ring-opened product 7 was obtained in high yield with good geometrical selectivity.

  在路易斯酸TMSOTf的存在下，芳基环丙基酮与芳基醛的开环反应在温和的条件下发生，以良好的产率得到2-（2-羟乙基）-1,3-二芳基丙烯酮。通过用三乙基甲硅烷基（TES）保护羟基，以高收率和良好的几何选择性获得了相应的开环产物7。
• A Novel Darzens type reaction promoted by tributylstannylcarbamate
  作者：Ikuya Shibata、Hayahide Yamasaki、Akio Baba、Haruo Matsuda

  DOI：10.1021/jo00051a043

  日期：1992.12

  Stannylcarbamate 1 proved to be a selective agent for generating organotin(IV) enolates from alpha-halo ketones. Thus, a Darzens reaction was achieved under mild and neutral conditions. The reaction took place without any side reactions and even with aliphatic alpha-halo ketones bearing enolizable alpha'-hydrogens. Various types of alpha,beta-epoxy ketones and esters were obtained in this one-pot reaction. The stereoselectivity of the reaction was influenced by changing the halogen substituent of the alpha-halo ketones and by additives. Moreover, the present method could be applied to gamma- and delta-halo ketones as enolate precursors, and five- and six-membered cyclic compounds were obtained.