N-(2,6-diphenyltetrahydro-2H-4-pyranyl)-acetamide | 38132-31-9

• 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: N-(2,6-diphenyltetrahydro-2H-4-pyranyl)-acetamide
• 英文别名: N1-(2,6-diphenyltetrahydro-2H-4-pyranyl)acetamide；N-(2,6-diphenyltetrahydro-2H-4-pyranyl)acetamide；N-[2,6-diphenyltetrahydropyran-4-yl]-acetamide；N-(2,6-diphenyltetrahydropyran-4-yl)acetamide；4-acetamido-2,6-diphenyltetrahydropyran；cis-2,6-diphenyl-4-acetylamino-oxane
• CAS: 38132-31-9
• 化学式: C₁₉H₂₁NO₂
• 分子量: 295.381
• InChiKey: GMMGIJDSULCMGY-LDLYASANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  cis-2,6-diphenyltetrahydro-4H-pyran-4-one 在 lithium aluminium tetrahydride 、 盐酸羟胺 、 sodium acetate 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 为溶剂， 反应 14.5h， 生成 N-(2,6-diphenyltetrahydro-2H-4-pyranyl)-acetamide
  参考文献：
  名称：

  Preparation and stereochemistry of some substituted 2,6-diphenyl-4-aminotetrahydropyrans

  摘要：

  DOI：

  10.1021/jo01310a018

文献信息

• CeCl3·7H2O/AcCl-catalyzed Prins–Ritter reaction sequence: a novel synthesis of 4-amido tetrahydropyran derivatives
  作者：J.S. Yadav、B.V. Subba Reddy、G.G.K.S. Narayana Kumar、G. Madhusudhan Reddy

  DOI：10.1016/j.tetlet.2007.05.056

  日期：2007.7

  compounds and nitriles undergo a smooth tandem Prins–Ritter type cyclization in the presence of CeCl3·7H2O/AcCl at ambient temperature to produce 4-amido tetrahydropyrans in high yields with all cis-selectivity. Spirocyclic 4-amido tetrahydropyrans are obtained in the case of cyclic ketones.

  在环境温度下，在CeCl 3 ·7H 2 O / AcCl存在下，均烯丙醇，羰基化合物和腈类进行顺式串联的Prins-Ritter型环化反应，以高收率和所有顺式选择性生成4-氨基四氢吡喃。在环状酮的情况下获得螺环的4-酰胺基四氢吡喃。
• Cerium(IV) sulfate catalyzed one-pot three-component diastereo selective synthesis of 4-amidotetrahydropyrans
  作者：Nagarajan Panneer Selvam、Paramasivan T. Perumal

  DOI：10.1139/v09-050

  日期：2009.6

  A convenient and diastereoselective one-pot synthesis of cis-4-amidotetrahydropyrans is described. This simple protocol involves Prins cyclization of homoallylic alcohol and aldehydes, followed by Ritter reaction of acetonitrile leading to the formation of cis-4-acetamidopyrans in good yields.

  本文介绍了一种方便且非对映选择性的顺式-4-脒基四氢吡喃的单锅合成方法。这个简单的方案涉及均烯丙基醇和醛的普林斯环化反应，然后是乙腈的里特反应，最终以良好的收率生成顺式-4-乙酰胺基四氢呋喃。
• 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.
• Three-component, one-pot diastereoselective synthesis of 4-amidotetrahydropyrans via the Prins–Ritter reaction sequence
  作者：J.S. Yadav、B.V. Subba Reddy、S. Aravind、G.G.K.S. Narayana Kumar、C. Madhavi、A.C. Kunwar

  DOI：10.1016/j.tet.2008.01.038

  日期：2008.3

  Three-component coupling of carbonyl compounds, homoallylic alcohols, and nitrites has been achieved using 20 mol % of phosphomolybdic acid (PMA) at ambient temperature via the Prins-Ritter sequence to furnish 4-amidotetrahydropyrans in high yields with all cis selectivity. Spirocyclic-4-amidotetrahydropyrans are obtained using cyclic ketones. (C) 2008 Elsevier Ltd. All rights reserved.
• Srinivasan; Perumal; Raja, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol. 50, # 8, p. 1083 - 1091
  作者：Srinivasan、Perumal、Raja

  DOI：——

  日期：——