(R)-4-Benzhydryl-3-prop-2-ynyl-oxazolidin-2-one | 256382-77-1

• 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: (R)-4-Benzhydryl-3-prop-2-ynyl-oxazolidin-2-one
• CAS: 256382-77-1
• 化学式: C₁₉H₁₇NO₂
• 分子量: 291.349
• InChiKey: KTLFHEFMILJLJD-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (R)-4-Benzhydryl-3-prop-2-ynyl-oxazolidin-2-one 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙腈 、 叔丁醇 为溶剂， 反应 48.0h， 生成
  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：

  3-溴丙炔 、 (R)-(+)-4-(二苯基甲基)-2-恶唑烷酮 以 四氢呋喃 为溶剂， 反应 16.0h， 以90%的产率得到(R)-4-Benzhydryl-3-prop-2-ynyl-oxazolidin-2-one
  参考文献：
  名称：

  (4R)-3-Allenyl-4-(diphenylmethyl)oxazolidin-2-one, an unsubstituted allenamide

  摘要：

  The first X-ray structure of an unsubstituted allenamide, C19H17NO2, is reported. The solid-state phase supports the notion that a key minimum conformation of allenamides can be invoked to rationalize the observed stereochemical outcomes in many of our methodological studies employing allenamides. This minimum conformation involves two important factors, i.e. having approximate coplanarity between the planes of the oxazolidinone ring and the internal olefin, and having the allene moiety facing away from the carbamate carbonyl group. The C-N-C=C torsion angle that quantifies this approximate coplanarity between the plane of the oxazolidinone ring and that of the internal olefin, as determined from this crystallographic study, is. 19.1 (2)degrees. A minimized structural calculation, which determined this angle to be -16.1degrees, is in close agreement. Additional structural features include a probable pi-pi interaction between the allene moiety and a benzene ring, and non-classical hydrogen bonding in the form of weak C-H...O interactions that are responsible for the formation of two-dimensional networks.

  DOI：

  10.1107/s0108270104023121

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。