N1-(2,6-diisopropyltetrahydro-2H-4-pyranyl)acetamide | 1068140-36-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: N1-(2,6-diisopropyltetrahydro-2H-4-pyranyl)acetamide
• 英文别名: N-(2,6-diisopropyltetrahydro-2H-4-pyranyl)acetamide
• CAS: 1068140-36-2
• 化学式: C₁₃H₂₅NO₂
• 分子量: 227.347
• InChiKey: XTNGXCDDQNJXEN-XYYAHUGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  异丁醛 、 乙腈 、 烯丙基三甲基硅烷 在 bismuth(lll) trifluoromethanesulfonate 作用下， 反应 0.5h， 以95%的产率得到N1-(2,6-diisopropyltetrahydro-2H-4-pyranyl)acetamide
  参考文献：
  名称：

  A Sakurai–Prins–Ritter reaction sequence for the diastereoselective synthesis of 4-amidotetrahydropyrans catalyzed by bismuth triflate

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2008.07.079

文献信息

• 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.