(R)-3-(hex-1-yn-1-yl)-4-phenyloxazolidin-2-one | 503590-24-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (R)-3-(hex-1-yn-1-yl)-4-phenyloxazolidin-2-one
• 英文别名: 2-Oxazolidinone, 3-(1-hexynyl)-4-phenyl-, (4R)-；(4R)-3-hex-1-ynyl-4-phenyl-1,3-oxazolidin-2-one
• CAS: 503590-24-7
• 化学式: C₁₅H₁₇NO₂
• 分子量: 243.305
• InChiKey: UWFQRDWHYKMTKO-AWEZNQCLSA-N

物化性质

• 沸点：
  351.3±45.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  (R)-3-(hex-1-yn-1-yl)-4-phenyloxazolidin-2-one 在 氯化铂 作用下， 以 1,2-二氯乙烷 为溶剂， 以40%的产率得到(R)-5-Pent-(E)-ylidene-5,9b-dihydro-1H-oxazolo[4,3-a]isoindol-3-one
  参考文献：
  名称：

  布朗斯台德酸催化的高度立体选择性芳烃-酰胺环化反应。在（+/-）-去溴阿糖胞苷A和C的总合成中，一种新颖的keteniminium Pictet-Spengler环化反应。

  摘要：

  [反应：见正文]描述了布朗斯台德酸催化的高度立体选择性的芳烃-氨酰胺环化反应。这些反应构成了Pictet-Spengler环化的酮亚胺变体，导致氮杂环和相关生物碱的有效合成。脱溴阿糖胞苷A和C的总合成作为该方法的首次应用在此处说明。

  DOI：

  10.1021/ol0473391
• 作为产物：
  描述：

  (R)-4-苯基-2-唑烷酮 、 1-己炔 在 吡啶 、 氧气 、 sodium carbonate 、 copper dichloride 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以50%的产率得到(R)-3-(hex-1-yn-1-yl)-4-phenyloxazolidin-2-one
  参考文献：
  名称：

  Regioselective TfOH-mediated hydroamidation of ynamides with nitriles

  摘要：

  A new TfOH-mediated reaction of ynamides with nitriles as nucleophiles has been developed. The reaction works efficiently under mild reaction conditions to afford a new class of alpha-acylaminoenamides readily via the intermediacy of keteniminium ion. The reaction displays generality and a broad substrates scope. Additionally, the alpha-acylaminoenamides could be transformed to highly substituted pyridine, 4-aminopyrimidine or isoquinoline cores. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2017.03.060

文献信息

• Copper-Catalyzed Alkynylation of Amides with Potassium Alkynyltrifluoroborates: A Room-Temperature, Base-Free Synthesis of Ynamides
  作者：Kévin Jouvin、François Couty、Gwilherm Evano

  DOI：10.1021/ol101322k

  日期：2010.7.16

  An efficient copper-mediated method for the coupling of potassium alkynyltrifluoroborates with nitrogen nucleophiles is reported. This reaction provides the first base-free and room-temperature synthesis of ynamides and allows for an easy preparation of these useful building blocks.

  报道了一种有效的铜介导的方法，用于将炔基三氟硼酸钾与氮亲核试剂偶联。该反应提供了首个无碱和室温下合成的酰胺，可轻松制备这些有用的结构单元。
• Pauson–Khand cycloaddition reactions of chiral ynamides. Observation of an unusual endo-addition with norbornadiene
  作者：Lichun Shen、Richard P. Hsung

  DOI：10.1016/j.tetlet.2003.10.064

  日期：2003.12

  Pauson–Khand cycloadditions using chiral ynamides are achieved in modest to good yields with excellent regioselectivity and modest stereoselectivity. An unusual endo addition is found when using norbornadiene and substituted ynamides, leading to cycloadducts that were not observed in previous studies using ynamides or ynamines.

  使用手性炔酰胺进行的Pauson-Khand环加成反应，产率适中，具有良好的区域选择性和适度的立体选择性。当使用降冰片二烯和取代的乙酰胺时，发现了一个不寻常的内含物，导致先前使用乙酰胺或乙胺的研究未观察到环加合物。
• A Copper-Catalyzed C−N Bond Formation Involving sp-Hybridized Carbons. A Direct Entry to Chiral Ynamides via N-Alkynylation of Amides
  作者：Michael O. Frederick、Jason A. Mulder、Michael R. Tracey、Richard P. Hsung、Jian Huang、Kimberly C. M. Kurtz、Lichun Shen、Christopher J. Douglas

  DOI：10.1021/ja021304j

  日期：2003.3.1

  A copper-catalyzed new C-N bond formation involving a sp-hybridized carbon is described here leading to a facile entry for syntheses of chiral ynamides. This direct N-alkynylation of amides should have a significant impact on the future development of synthetic methodologies employing 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.