tert-butyl (2,6-dimethylphenyl) fumarate | 1378314-79-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: tert-butyl (2,6-dimethylphenyl) fumarate
• 英文别名: 4-O-tert-butyl 1-O-(2,6-dimethylphenyl) (E)-but-2-enedioate
• CAS: 1378314-79-4
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: DDVARLNTYZHGFI-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (2,6-dimethylphenyl) fumarate 、 苯硼酸 在 chlorobis(ethylene)rhodium(I) dimer 、 (S,S)-1,7,7-trimethyl-2,5-diphenylbicyclo[2.2.1]hepta-2,5-diene 、 potassium tert-butylate 作用下， 以 甲醇 、 二氯甲烷 、 异丙醇 为溶剂， 反应 0.75h， 以58%的产率得到(S)-1-tert-butyl 4-(2,6-dimethylphenyl) 2-phenylsuccinate
  参考文献：
  名称：

  Preparation of Chiral 3-Arylpyrrolidines via the Enantioselective 1,4-Addition of Arylboronic Acids to Fumaric Esters Catalyzed by Rh(I)/Chiral Diene Complexes

  摘要：

  A highly efficient rhodium-catalyzed protocol for the preparation of 2-arylsuccinic esters and 3-arylpyrrolidines of high optical purity has been achieved. In the presence of 1 mol % of a chiral diene/Rh(I) catalyst, asymmetric addition of various arylboronic acids to di-fert-butyl fumarate (3c) provides the corresponding adducts in up to 99% yield and 94 -> 99.5% ee. Excellent enantioselectivities were also observed in the regio- and enantioselective conjugate addition of phenylboronic acid (4a) to compound 3e.

  DOI：

  10.1021/ol300980k
• 作为产物：
  描述：

  2,6-二甲基苯酚 、 富马酸叔-丁酯 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以72%的产率得到tert-butyl (2,6-dimethylphenyl) fumarate
  参考文献：
  名称：

  Preparation of Chiral 3-Arylpyrrolidines via the Enantioselective 1,4-Addition of Arylboronic Acids to Fumaric Esters Catalyzed by Rh(I)/Chiral Diene Complexes

  摘要：

  A highly efficient rhodium-catalyzed protocol for the preparation of 2-arylsuccinic esters and 3-arylpyrrolidines of high optical purity has been achieved. In the presence of 1 mol % of a chiral diene/Rh(I) catalyst, asymmetric addition of various arylboronic acids to di-fert-butyl fumarate (3c) provides the corresponding adducts in up to 99% yield and 94 -> 99.5% ee. Excellent enantioselectivities were also observed in the regio- and enantioselective conjugate addition of phenylboronic acid (4a) to compound 3e.

  DOI：

  10.1021/ol300980k

文献信息

• Preparation of Chiral 3-Arylpyrrolidines via the Enantioselective 1,4-Addition of Arylboronic Acids to Fumaric Esters Catalyzed by Rh(I)/Chiral Diene Complexes
  作者：Yu-Chiang, Chung、Damodar Janmanchi、Hsyueh-Liang Wu

  DOI：10.1021/ol300980k

  日期：2012.6.1

  A highly efficient rhodium-catalyzed protocol for the preparation of 2-arylsuccinic esters and 3-arylpyrrolidines of high optical purity has been achieved. In the presence of 1 mol % of a chiral diene/Rh(I) catalyst, asymmetric addition of various arylboronic acids to di-fert-butyl fumarate (3c) provides the corresponding adducts in up to 99% yield and 94 -> 99.5% ee. Excellent enantioselectivities were also observed in the regio- and enantioselective conjugate addition of phenylboronic acid (4a) to compound 3e.