(3aS,8aR)-3p(phenylethynyl)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d]oxazol-2-one | 425605-15-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (3aS,8aR)-3p(phenylethynyl)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d]oxazol-2-one
• 英文别名: (3aR,8bS)-1-(2-phenylethynyl)-4,8b-dihydro-3aH-indeno[1,2-d][1,3]oxazol-2-one
• CAS: 425605-15-8
• 化学式: C₁₈H₁₃NO₂
• 分子量: 275.307
• InChiKey: USORLUWRLCVAHR-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  (3aS,8aR)-3p(phenylethynyl)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d]oxazol-2-one 在 水 、 magnesium iodide 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到(3aS,8aR)-3-((E)-1-Iodo-2-phenyl-vinyl)-3,3a,8,8a-tetrahydro-indeno[1,2-d]oxazol-2-one
  参考文献：
  名称：

  Highly Stereoselective Synthesis of Novel α-Haloenamides via a Mild and Efficient Hydrohalogenation of Ynamides

  摘要：

  A highly stereoselective preparation of novel chiral (E)-alpha-haloenamides under mild conditions utilizing magnesium halide salts is described. This unexpected mild and efficient hydrohalogenation reaction highlights another synthetic utility of ynamides.

  DOI：

  10.1021/ol0300266
• 作为产物：
  描述：

  (3aS-顺)-(-)-3,3a,8,8a-四氢-2H-茚并[1,2-d]噁唑-2-酮 、 苯基溴乙炔 在 potassium phosphate 、 N,N'-二甲基乙二胺 作用下， 以 甲苯 为溶剂， 以65%的产率得到(3aS,8aR)-3p(phenylethynyl)-3,3a,8,8a-tetrahydro-2H-indeno[1,2-d]oxazol-2-one
  参考文献：
  名称：

  A Copper-Catalyzed C−N Bond Formation Involving sp-Hybridized Carbons. A Direct Entry to Chiral Ynamides via N-Alkynylation of Amides

  摘要：

  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.

  DOI：

  10.1021/ja021304j

文献信息

• Copper-Catalyzed Alkynylation of Amides with Potassium Alkynyltrifluoroborates: A Room-Temperature, Base-Free Synthesis of Ynamides
  作者：Kévin Jouvin、François Couty、Gwilherm Evano

  DOI：10.1021/ol101322k

  日期：2010.7.16

  An efficient copper-mediated method for the coupling of potassium alkynyltrifluoroborates with nitrogen nucleophiles is reported. This reaction provides the first base-free and room-temperature synthesis of ynamides and allows for an easy preparation of these useful building blocks.

  报道了一种有效的铜介导的方法，用于将炔基三氟硼酸钾与氮亲核试剂偶联。该反应提供了首个无碱和室温下合成的酰胺，可轻松制备这些有用的结构单元。
• The First Stereoselective Ficini−Claisen Rearrangement Using Chiral Ynamides
  作者：Jason A. Mulder、Richard P. Hsung、Michael O. Frederick、Michael R. Tracey、Craig A. Zificsak

  DOI：10.1021/ol020037j

  日期：2002.4.1

  [GRAPHICS]The first asymmetric Ficini-Claisen rearrangement using chiral ynamides is described. At relatively low temperatures, the Ficini-Claisen rearrangement can be efficiently promoted by p-nitrobenzenesulfonic acid leading to high diastereoselectivity for a range of different allylic alcohols and chiral 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.
• 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.
• Highly Stereoselective Synthesis of Novel α-Haloenamides via a Mild and Efficient Hydrohalogenation of Ynamides
  作者：Jason A. Mulder、Kimberly C. M. Kurtz、Richard P. Hsung、Heather Coverdale、Michael O. Frederick、Lichun Shen、Craig A. Zificsak

  DOI：10.1021/ol0300266

  日期：2003.5.1

  A highly stereoselective preparation of novel chiral (E)-alpha-haloenamides under mild conditions utilizing magnesium halide salts is described. This unexpected mild and efficient hydrohalogenation reaction highlights another synthetic utility of ynamides.