cis-3-benzoyl-2-phenyltetrahydropyran | 144667-68-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-3-benzoyl-2-phenyltetrahydropyran
• 英文别名: phenyl-[(2R,3S)-2-phenyloxan-3-yl]methanone
• CAS: 144667-68-5；144667-69-6
• 化学式: C₁₈H₁₈O₂
• 分子量: 266.34
• InChiKey: CSFIBEAMBHBXGC-AEFFLSMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  5-iodo-1-phenylpentan-1-one 、 苯甲醛 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 trans-3-benzoyl-2-phenyltetrahydropyran 、 cis-3-benzoyl-2-phenyltetrahydropyran
  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