3-[6-(2-Methoxy-6-methylphenyl)-1,3-dihydro-2-benzofuran-5-yl]-4,4-dimethyl-1,3-oxazolidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 3-[6-(2-Methoxy-6-methylphenyl)-1,3-dihydro-2-benzofuran-5-yl]-4,4-dimethyl-1,3-oxazolidin-2-one
• 英文别名: 3-[6-(2-methoxy-6-methylphenyl)-1,3-dihydro-2-benzofuran-5-yl]-4,4-dimethyl-1,3-oxazolidin-2-one
• 化学式: C₂₁H₂₃NO₄
• 分子量: 353.418
• InChiKey: GTTLKBZGERESAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-[2-(2-Methoxy-6-methylphenyl)ethynyl]-4,4-dimethyl-1,3-oxazolidin-2-one 、 丙炔醚 在 bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate (S)-xylyl-BINAP 、 4 A molecular sieve 作用下， 以 1,2-二氯乙烷 为溶剂， 以95%的产率得到3-[6-(2-Methoxy-6-methylphenyl)-1,3-dihydro-2-benzofuran-5-yl]-4,4-dimethyl-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Stereochemical Control of Both C−C and C−N Axial Chirality in the Synthesis of Chiral N,O-Biaryls

  摘要：

  A Rh(l)-catalyzed asymmetric [2 + 2 + 2] cycloaddition of achiral ynamides is described here. This work demonstrates a unique concept of stereochemical control of both the C-C and C-N axial chirality and provides an approach to the synthesis of chiral N,O-biaryls as well as chiral anilides.

  DOI：

  10.1021/ol701692m

文献信息

• Stereochemical Control of Both C−C and C−N Axial Chirality in the Synthesis of Chiral <i>N</i>,<i>O-</i>Biaryls
  作者：Jossian Oppenheimer、Richard P. Hsung、Ruth Figueroa、Whitney L. Johnson

  DOI：10.1021/ol701692m

  日期：2007.9.1

  A Rh(l)-catalyzed asymmetric [2 + 2 + 2] cycloaddition of achiral ynamides is described here. This work demonstrates a unique concept of stereochemical control of both the C-C and C-N axial chirality and provides an approach to the synthesis of chiral N,O-biaryls as well as chiral anilides.
• A rhodium(I)-xylyl-BINAP catalyzed asymmetric ynamide-[2+2+2] cycloaddition in the synthesis of optically enriched N,O-biaryls
  作者：Jossian Oppenheimer、Whitney L. Johnson、Ruth Figueroa、Ryuji Hayashi、Richard P. Hsung

  DOI：10.1016/j.tet.2009.03.078

  日期：2009.6

  A rhodium(I)-xylyl-BINAP catalyzed asymmetric [2+2+2] cycloaddition of achiral conjugated aryl ynamides with various diynes is described here. This asymmetric cycloaddition provides a series of structurally interesting chiral N,O-biaryls with excellent enantioselectivity along with a modest diastereoselectivity, with respect to both C-C and C-N axial chirality. (C) 2009 Elsevier Ltd. All rights reserved.