(R)-4-phenyl-3-(2-triisopropylsilylethynyl)oxazolidin-2-one | 503590-28-1

• 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-phenyl-3-(2-triisopropylsilylethynyl)oxazolidin-2-one
• 英文别名: (4R)-4-phenyl-3-[2-tri(propan-2-yl)silylethynyl]-1,3-oxazolidin-2-one
• CAS: 503590-28-1
• 化学式: C₂₀H₂₉NO₂Si
• 分子量: 343.541
• InChiKey: VDZCKNSJAMCWGC-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.36
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 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-phenyl-3-(2-triisopropylsilylethynyl)oxazolidin-2-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以70%的产率得到(4R)-3-乙炔基-4-苯基-1,3-恶唑烷-2-酮
  参考文献：
  名称：

  Y酰胺的钯催化甲硅烷基氰化：区域和立体选择性获得四取代的3-甲硅烷基-2-氨基丙烯腈

  摘要：

  由于缺乏以受控方式合成它们的方法，四取代的 2-氨基丙烯腈（α-烯氨基腈）是未被充分研究的组成部分。描述了对这些有价值的支架的一般访问以及机械研究和 DFT 计算。这种高度区域和立体选择性的策略依赖于使用 ynamides 的第一个分子间甲硅烷基氰化。

  DOI：

  10.1002/anie.202200204
• 作为产物：
  描述：

  三异丙基硅基乙炔 在 potassium phosphate 、 正丁基锂 、 1,10-菲罗啉 、 copper(II) sulfate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 53.75h， 生成 (R)-4-phenyl-3-(2-triisopropylsilylethynyl)oxazolidin-2-one
  参考文献：
  名称：

  铜（II）催化炔基溴化物作为Ynamides和通用合成酰胺化ž -Enamides。分子内酰胺化反应合成大环酰胺

  摘要：

  在此描述了用于将各种酰胺与炔基溴化物偶联的通用且有效的方法。这种新颖的酰胺化反应涉及使用五水合硫酸铜（II）和1,10-菲咯啉来指导sp-C-N键形成的催化方案，从而通过分子内酰胺化形成结构上多样的酰胺，包括大环酰胺。鉴于对酰胺化学的浓厚兴趣，这种原子经济的酰胺合成方法应引起有机合成界的进一步关注。

  DOI：

  10.1021/jo060230h

文献信息

• Tandem azidination– and hydroazidination–Huisgen [3 + 2] cycloadditions of ynamides. Synthesis of chiral amide-substituted triazoles
  作者：Xuejun Zhang、Richard P. Hsung、Lingfeng You

  DOI：10.1039/b606680a

  日期：——

  Tandem azidination- and hydroazidination-Huisgen [3 + 2] cycloadditions of ynamides are described here. These processes are regioselective and chemoselective, leading to the synthesis of chiral amide-substituted triazoles.

  此处描述了酰胺的串联叠氮化和加氢叠氮化-Huisgen [3 + 2]环加成。这些过程是区域选择性的和化学选择性的，导致手性酰胺取代的三唑的合成。
• Copper Sulfate-Pentahydrate-1,10-Phenanthroline Catalyzed Amidations of Alkynyl Bromides. Synthesis of Heteroaromatic Amine Substituted Ynamides
  作者：Yanshi Zhang、Richard P. Hsung、Michael R. Tracey、Kimberly C. M. Kurtz、Eymi L. Vera

  DOI：10.1021/ol049827e

  日期：2004.4.1

  A practical cross-coupling of amides with alkynyl bromides using catalytic CuSO(4)(.)5H(2)O and 1,10-phenanthroline is described here. This catalytic protocol is more environmentally friendly than the use of CuCN or copper halides and provides a general entry for syntheses of ynamides including various new sulfonyl and heteroaromatic amine substituted ynamides. Given the interest in ynamides, this N-alkynylation of amides should be significant for the future of ynamides in organic synthesis.
• 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 α-Keto-Imides via Oxidation of Ynamides
  作者：Ziyad F. Al-Rashid、Whitney L. Johnson、Richard P. Hsung、Yonggang Wei、Pei-Yuan Yao、Renhei Liu、Kang Zhao

  DOI：10.1021/jo8015067

  日期：2008.11.21

  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.
• Highly Substituted 2-Amido-furans From Rh(II)-Catalyzed Cyclopropenations of Ynamides
  作者：Hongyan Li、Richard P. Hsung

  DOI：10.1021/ol901860b

  日期：2009.10.1

  Rh(II)-catalyzed cyclopropenations of ynamides are described. Although an actual amido-cyclopropene intermediate may not be involved, these reactions provide a facile entry to highly substituted 2-amido-turans, thereby formerly constituting a [3 + 2] cycloaddition. An application of these de novo 2-amido-turans in N-tethered intramolecular [4 + 2] cycloadditions is also illustrated, leading to dihydroindoles and tetrahydroquinolines.