(4R,5S)-4,5-Diphenyl-3-propa-1,2-dienyl-oxazolidin-2-one | 256382-51-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (4R,5S)-4,5-Diphenyl-3-propa-1,2-dienyl-oxazolidin-2-one
• CAS: 256382-51-1
• 化学式: C₁₈H₁₅NO₂
• 分子量: 277.323
• InChiKey: DTSFKVRBELBMEC-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  丁烯酮 、 (4R,5S)-4,5-Diphenyl-3-propa-1,2-dienyl-oxazolidin-2-one 以 乙腈 为溶剂， 反应 89.0h， 生成 (4R,5S)-3-[(2S)-6-methyl-3-methylidene-4H-pyran-2-yl]-4,5-diphenyl-1,3-oxazolidin-2-one 、
  参考文献：
  名称：

  First Stereoselective Inverse Demand [4 + 2] Cycloaddition Reactions of Novel Chiral Allenamides with Heterodienes. Preparation of Highly Functionalized 2-Arylpyranyl Heterocycles

  摘要：

  The first stereoselective inverse demand [4 + 2] cycloaddition reactions of chiral allenamides with heterodienes are described here. These reactions lead to stereoselective synthesis of highly functionalized pyranyl heterocycles. A mechanistic model is also proposed here based on the stereochemical assignment and comparisons of stereoselectivities obtained from various chiral allenamides.

  DOI：

  10.1021/ol990345q
• 作为产物：
  描述：

  (4R,5S)-(+)-顺-4,5-二苯基-2-恶唑烷酮 在 potassium tert-butylate 、 sodium hydride 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 0.5h， 生成 (4R,5S)-4,5-Diphenyl-3-propa-1,2-dienyl-oxazolidin-2-one
  参考文献：
  名称：

  First Stereoselective Inverse Demand [4 + 2] Cycloaddition Reactions of Novel Chiral Allenamides with Heterodienes. Preparation of Highly Functionalized 2-Arylpyranyl Heterocycles

  摘要：

  The first stereoselective inverse demand [4 + 2] cycloaddition reactions of chiral allenamides with heterodienes are described here. These reactions lead to stereoselective synthesis of highly functionalized pyranyl heterocycles. A mechanistic model is also proposed here based on the stereochemical assignment and comparisons of stereoselectivities obtained from various chiral allenamides.

  DOI：

  10.1021/ol990345q

文献信息

• Efficient preparations of novel ynamides and allenamides
  作者：Lin-Li Wei、Jason A. Mulder、Hui Xiong、Craig A. Zificsak、Christopher J. Douglas、Richard P. Hsung

  DOI：10.1016/s0040-4020(00)01014-0

  日期：2001.1

  achiral allenamides, ynamides are prepared from enamides via bromination followed by base-induced elimination of the Z-bromoenamides. These ynamides and allenamides possess improved thermal stability compared to ynamines and allenamines. They can be isolated, purified, and handled with ease, and thus, should be synthetically more useful than traditional ynamines and allenamines.

  在此描述了一系列新型的酰胺和烯丙酰胺的实用合成。尽管炔丙基酰胺的碱诱导的异构化方案导致一系列手性和非手性烯丙酰胺，但是通过溴化由酰胺制备炔基酰胺，然后进行碱诱导的Z-溴烯酰胺的消除。与炔胺和烯丙胺相比，这些炔酰胺和烯丙酰胺具有改进的热稳定性。它们可以轻松分离，纯化和处理，因此在合成上应比传统的ynamines和allenamines更有用。
• First Stereoselective Inverse Demand [4 + 2] Cycloaddition Reactions of Novel Chiral Allenamides with Heterodienes. Preparation of Highly Functionalized 2-Arylpyranyl Heterocycles
  作者：Lin-Li Wei、Richard P. Hsung、Hui Xiong、Jason A. Mulder、Nancy T. Nkansah

  DOI：10.1021/ol990345q

  日期：1999.12.1

  The first stereoselective inverse demand [4 + 2] cycloaddition reactions of chiral allenamides with heterodienes are described here. These reactions lead to stereoselective synthesis of highly functionalized pyranyl heterocycles. A mechanistic model is also proposed here based on the stereochemical assignment and comparisons of stereoselectivities obtained from various chiral allenamides.