(4S,5R)-1-(2-Methoxy-naphthalen-1-ylethynyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one | 683246-72-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (4S,5R)-1-(2-Methoxy-naphthalen-1-ylethynyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one
• CAS: 683246-72-2
• 化学式: C₂₄H₂₂N₂O₂
• 分子量: 370.451
• InChiKey: ZIBUCMBTMWZKEN-SBUREZEXSA-N

物化性质

• 沸点：
  539.2±60.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  32.78
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4S,5R)-1-(2-Methoxy-naphthalen-1-ylethynyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one 在 Wilkinson's catalyst silver(I) salt 作用下， 以 二氯甲烷 为溶剂， 以24%的产率得到(4S,5R)-1-benzo[e][1]benzofuran-2-yl-3,4-dimethyl-5-phenylimidazolidin-2-one
  参考文献：
  名称：

  A Rhodium(I)-Catalyzed Demethylation−Cyclization of o-Anisole-Substituted Ynamides in the Synthesis of Chiral 2-Amido Benzofurans

  摘要：

  A Rh(I)-catalyzed demethylation-cyclization sequence for a direct transformation of o-anisole-substituted ynamides to benzofurans is described here. The Ag salt functions synergistically with Rh(I) for the key demethylation step.

  DOI：

  10.1021/ol0707362
• 作为产物：
  描述：

  1-(2',2'-dibromovinyl)-2-methoxynaphthalene 在 氢氧化钾 、 potassium phosphate 、 1,10-菲罗啉 、 copper (II) sulfite 、 苄基三乙基氯化铵 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 6.0h， 生成 (4S,5R)-1-(2-Methoxy-naphthalen-1-ylethynyl)-3,4-dimethyl-5-phenyl-imidazolidin-2-one
  参考文献：
  名称：

  Copper Sulfate-Pentahydrate-1,10-Phenanthroline Catalyzed Amidations of Alkynyl Bromides. Synthesis of Heteroaromatic Amine Substituted Ynamides

  摘要：

  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.

  DOI：

  10.1021/ol049827e

文献信息

• Copper(II)-Catalyzed Amidations of Alkynyl Bromides as a General Synthesis of Ynamides and <i>Z</i>-Enamides. An Intramolecular Amidation for the Synthesis of Macrocyclic Ynamides
  作者：Xuejun Zhang、Yanshi Zhang、Jian Huang、Richard P. Hsung、Kimberly C. M. Kurtz、Jossian Oppenheimer、Matthew E. Petersen、Irina K. Sagamanova、Lichun Shen、Michael R. Tracey

  DOI：10.1021/jo060230h

  日期：2006.5.1

  method for the coupling of a wide range of amides with alkynyl bromides is described here. This novel amidation reaction involves a catalytic protocol using copper(II) sulfate-pentahydrate and 1,10-phenanthroline to direct the sp-C−N bond formation, leading to a structurally diverse array of ynamides including macrocyclic ynamides via an intramolecular amidation. Given the surging interest in ynamide chemistry

  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。
• Rhodium(I)-Catalyzed [2 + 2 + 2] Cycloadditions of Ynamides in the Synthesis of Amide-Substituted Chiral Biaryls
  作者：Michael R. Tracey、Jossian Oppenheimer、Richard P. Hsung

  DOI：10.1021/jo061683p

  日期：2006.10.1

  Rhodium(I)-catalyzed [2 + 2 + 2] cycloadditions of sterically encumbered aryl-substituted ynamides with various diynes are described here. These cycloadditions provide the synthesis of an array of new chiral amide-substituted biaryls that can be useful in future chiral ligand designs.

  在此描述了铑（I）催化的，空间位阻的芳基取代的乙酰胺与各种二炔的[2 + 2 + 2]环加成反应。这些环加成提供了新的手性酰胺取代的联芳基阵列的合成，这些阵列可用于未来的手性配体设计中。