4-acetamido-2,6-di(p-tolyl)-tetrahydro-pyran | 1007233-13-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 4-acetamido-2,6-di(p-tolyl)-tetrahydro-pyran
• CAS: 1007233-13-7
• 化学式: C₂₁H₂₅NO₂
• 分子量: 323.435
• InChiKey: UHYCURGPTYIANG-MZADTFQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  对甲基苯甲醛 、 乙腈 、 烯丙基三甲基硅烷 在 三氟化硼乙醚 作用下， 反应 36.0h， 以60%的产率得到4-acetamido-2,6-di(p-tolyl)-tetrahydro-pyran
  参考文献：
  名称：

  Stereoselective One-Pot, Three-Component Synthesis of 4-Amidotetrahydropyran

  摘要：

  [GRAPHICS]The reaction of aldehyde with allylsilane in acetonitrile mediated by boron trifluoride etherate generated 4-aminotetrahydropyrans in good yields. The product is highly stereoselective.

  DOI：

  10.1021/jo7023366

文献信息

• A Sakurai–Prins–Ritter reaction sequence for the diastereoselective synthesis of 4-amidotetrahydropyrans catalyzed by bismuth triflate
  作者：Gowravaram Sabitha、M. Bhikshapathi、Sambit Nayak、J.S. Yadav、R. Ravi、A.C. Kunwar

  DOI：10.1016/j.tetlet.2008.07.079

  日期：2008.9

  The synthesis of 4-amidotetrahydropyrans has been achieved by a single-step Sakurai-Prins-Ritter reaction sequence in a domino fashion by the reaction of an aldehyde and allyltrimethylsilane in acetonitrile using Bi(OTf)(3) as catalyst. The present synthesis is highly efficient and diastereoselective. (C) 2008 Elsevier Ltd. All rights reserved.
• Molecular Iodine–Catalyzed, One-Pot, Diastereoselective Synthesis of 4-Amido Tetrahydropyrans
  作者：Gowravaram Sabitha、M. Bhikshapathi、Sambit Nayak、J. S. Yadav

  DOI：10.1080/00397910903422534

  日期：2010.12.21

  A simple and efficient one-pot synthesis of symmetrical 4-amido tetrahydropyrans via the Sakurai-Prins-Ritter reaction sequence using molecular iodine as catalyst from an aldehyde and allyltrimethylsilane in acetonitrile is described. This new method has the advantage of good to excellent yields (60-98%) and short reaction times (20-150min) at ambient temperature with high diastereoselectivity.