(4R)-4-benzhydryl-3-hex-1-ynyl-1,3-oxazolidin-2-one | 425605-06-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4R)-4-benzhydryl-3-hex-1-ynyl-1,3-oxazolidin-2-one
• CAS: 425605-06-7
• 化学式: C₂₂H₂₃NO₂
• 分子量: 333.43
• InChiKey: DANYOXGSPDZFPY-FQEVSTJZSA-N

物化性质

• 沸点：
  449.0±38.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R)-4-benzhydryl-3-hex-1-ynyl-1,3-oxazolidin-2-one 在 水 、 magnesium iodide 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到(R)-4-Benzhydryl-3-((E)-1-iodo-hex-1-enyl)-oxazolidin-2-one
  参考文献：
  名称：

  Highly Stereoselective Synthesis of Novel α-Haloenamides via a Mild and Efficient Hydrohalogenation of Ynamides

  摘要：

  A highly stereoselective preparation of novel chiral (E)-alpha-haloenamides under mild conditions utilizing magnesium halide salts is described. This unexpected mild and efficient hydrohalogenation reaction highlights another synthetic utility of ynamides.

  DOI：

  10.1021/ol0300266

文献信息

• The First Stereoselective Ficini−Claisen Rearrangement Using Chiral Ynamides
  作者：Jason A. Mulder、Richard P. Hsung、Michael O. Frederick、Michael R. Tracey、Craig A. Zificsak

  DOI：10.1021/ol020037j

  日期：2002.4.1

  [GRAPHICS]The first asymmetric Ficini-Claisen rearrangement using chiral ynamides is described. At relatively low temperatures, the Ficini-Claisen rearrangement can be efficiently promoted by p-nitrobenzenesulfonic acid leading to high diastereoselectivity for a range of different allylic alcohols and chiral ynamides.
• Synthesis of chiral allenes from ynamides through a highly stereoselective Saucy–Marbet rearrangement
  作者：Kimberly C.M. Kurtz、Michael O. Frederick、Robert H. Lambeth、Jason A. Mulder、Michael R. Tracey、Richard P. Hsung

  DOI：10.1016/j.tet.2005.11.087

  日期：2006.4

  A highly stereoselective Saucy-Marbet rearrangement using chiral ynamides and propargyl alcohols is described here. This rearrangement can be catalyzed by para-nitrobenzenesulfonic acid and leads to high diastereoselectivities for a range of different chiral propargyl alcohols and ynamides in a stereochemically intriguing matched, mismatched or indifferent manner. The stereoselective Saucy-Marbet rearrangement of ynamides provides an excellent entry to highly substituted chiral homo allenyl alcohols. (c) 2006 Elsevier Ltd. All rights reserved.
• Highly Stereoselective Saucy−Marbet Rearrangement Using Chiral Ynamides. Synthesis of Highly Substituted Chiral Homoallenyl Alcohols
  作者：Michael O. Frederick、Richard P. Hsung、Robert H. Lambeth、Jason A. Mulder、Michael R. Tracey

  DOI：10.1021/ol030061c

  日期：2003.7.1

  [GRAPHICS]A highly stereoselective Saucy-Marbet rearrangement using chiral ynamides and propargyl alcohols is described here. This rearrangement can be catalyzed by para-nitrobenzenesulfonic acid leading to high diastereoselectivities for a range of different chiral propargyl alcohols and ynamides in a stereochemically intriguing matched, mismatched, or indifferent manner. This provides an excellent entry to highly substituted chiral homoallenyl alcohols.
• Highly Stereoselective Synthesis of Novel α-Haloenamides via a Mild and Efficient Hydrohalogenation of Ynamides
  作者：Jason A. Mulder、Kimberly C. M. Kurtz、Richard P. Hsung、Heather Coverdale、Michael O. Frederick、Lichun Shen、Craig A. Zificsak

  DOI：10.1021/ol0300266

  日期：2003.5.1

  A highly stereoselective preparation of novel chiral (E)-alpha-haloenamides under mild conditions utilizing magnesium halide salts is described. This unexpected mild and efficient hydrohalogenation reaction highlights another synthetic utility of ynamides.