(R)-4-Benzyl-3-oct-1-ynyl-oxazolidin-2-one | 503590-32-7

• 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)-4-Benzyl-3-oct-1-ynyl-oxazolidin-2-one
• 英文别名: (4R)-4-Benzyl-3-(oct-1-YN-1-YL)-1,3-oxazolidin-2-one；(4R)-4-benzyl-3-oct-1-ynyl-1,3-oxazolidin-2-one
• CAS: 503590-32-7
• 化学式: C₁₈H₂₃NO₂
• 分子量: 285.386
• InChiKey: AQFYHILVNCIVEC-QGZVFWFLSA-N

物化性质

• 沸点：
  389.7±25.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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)-4-Benzyl-3-oct-1-ynyl-oxazolidin-2-one 在 sodium periodate 、 ruthenium(IV) oxide hydrate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 4.0h， 以85%的产率得到(R)-1-(4-benzyl-2-oxooxazolidin-3-yl)octane-1,2-dione
  参考文献：
  名称：

  Synthesis of α-Keto-Imides via Oxidation of Ynamides

  摘要：

  A de novo preparation of alpha-keto-imides via ynamide oxidation is described. With a number of alkyne oxidation conditions screened, a highly efficient RuO2-NaIO4 mediated oxidation and a DMDO oxidation have been identified to tolerate a wide range of ynamide types. In addition to accessing a wide variety of a-keto-imides, the RuO2-NaIO4 protocol provides a novel entry to the vicinal tricarboryl motif via oxidation of push-pull ynamides, and imido acylsilanes from silyl-substituted ynamides. Chemoselective oxidation of ynamides containing olefins can be achieved by using DMDO, while the RuO2-NaIO4 protocol is not effective. These studies provide further support for the synthetic utility of ynamides.

  DOI：

  10.1021/jo8015067
• 作为产物：
  描述：

  1-bromo-1-octyne 、 (R)-4-苄基-2-噁唑烷酮 在 potassium phosphate 、 1,10-菲罗啉 、 copper(ll) sulfate pentahydrate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 (R)-4-Benzyl-3-oct-1-ynyl-oxazolidin-2-one
  参考文献：
  名称：

  Sc（OTf）3催化的亚胺和酮加成反应制备叔型β-羟基羧酰胺。

  摘要：

  通过Sc（OTf）3催化的酰胺和取代酮的加成，已经开发出一种有效的途径来获得官能化的叔型β-羟基羧酰胺。发现水是重要的反应底物，在该过程中不需要溶剂。广泛的取代的乙酰胺和酮以优异的化学选择性很好地适用于该反应。此外，制备了几种具有优异的区域选择性和出色的非对映选择性的手性β-羟基羧酰胺3j-3r。

  DOI：

  10.1021/acs.joc.9b02854

文献信息

• Brønsted Acid-Catalyzed Highly Stereoselective Arene-Ynamide Cyclizations. A Novel Keteniminium Pictet−Spengler Cyclization in Total Syntheses of (±)-Desbromoarborescidines A and C
  作者：Yanshi Zhang、Richard P. Hsung、Xuejun Zhang、Jian Huang、Brian W. Slafer、Allison Davis

  DOI：10.1021/ol0473391

  日期：2005.3.1

  [reaction: see text] A Bronsted acid-catalyzed highly stereoselective arene-ynamide cyclization is described. These reactions constitute a keteniminium variant of Pictet-Spengler cyclizations, leading to efficient synthesis of nitrogen heterocycles and related alkaloids. Total syntheses of desbromoarborescidines A and C are illustrated here as first applications of this methodology.

  [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。
• 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.