(4aR,8aS)-4a,5,8,8a-tetrahydro-6-(triisopropylsilyl)oxynaphthalene-1,4-dione | 691390-89-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aR,8aS)-4a,5,8,8a-tetrahydro-6-(triisopropylsilyl)oxynaphthalene-1,4-dione
• 英文别名: (4aR,8aS)-6-tri(propan-2-yl)silyloxy-4a,5,8,8a-tetrahydronaphthalene-1,4-dione
• CAS: 691390-89-3
• 化学式: C₁₉H₃₀O₃Si
• 分子量: 334.531
• InChiKey: UAZIHTQBFDEYAH-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4aR,8aS)-4a,5,8,8a-tetrahydro-6-(triisopropylsilyl)oxynaphthalene-1,4-dione 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以68%的产率得到(1R,4S,4aR,8aS)-1,4,4a,5,8,8a-hexahydro-6-(triisopropylsilyl)oxynaphthalene-1,4-diol
  参考文献：
  名称：

  Enantioselective and Structure-Selective Diels−Alder Reactions of Unsymmetrical Quinones Catalyzed by a Chiral Oxazaborolidinium Cation. Predictive Selection Rules

  摘要：

  The chiral oxazaborolidinium cation 1 promotes Diels-Alder reactions between 2-triisopropylsilyloxy-1,3-butadiene and a number of unsymmetrical 1,4-benzoquinones in a highly enantioselective and structurally selective manner. The basis for the enantioselectivity is explained rationally in terms of a preferred type of transition-state assembly. Selection rules have been developed that allow the prediction of the principal reaction product of Diels-Alder reaction between unsymmetrical diene and quinone components.

  DOI：

  10.1021/ja049323b
• 作为产物：
  描述：

  2-(triisopropylsiloxy)-1,3-butadiene 、 对苯醌 在 oxazaborolidinium⁽¹⁺⁾*Tf₂N^(1-) 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (4aS,8aR)-4a,5,8,8a-tetrahydro-6-(triisopropylsilyl)oxynaphthalene-1,4-dione 、 (4aR,8aS)-4a,5,8,8a-tetrahydro-6-(triisopropylsilyl)oxynaphthalene-1,4-dione
  参考文献：
  名称：

  Enantioselective and Structure-Selective Diels−Alder Reactions of Unsymmetrical Quinones Catalyzed by a Chiral Oxazaborolidinium Cation. Predictive Selection Rules

  摘要：

  The chiral oxazaborolidinium cation 1 promotes Diels-Alder reactions between 2-triisopropylsilyloxy-1,3-butadiene and a number of unsymmetrical 1,4-benzoquinones in a highly enantioselective and structurally selective manner. The basis for the enantioselectivity is explained rationally in terms of a preferred type of transition-state assembly. Selection rules have been developed that allow the prediction of the principal reaction product of Diels-Alder reaction between unsymmetrical diene and quinone components.

  DOI：

  10.1021/ja049323b

文献信息

• Enantioselective and Structure-Selective Diels−Alder Reactions of Unsymmetrical Quinones Catalyzed by a Chiral Oxazaborolidinium Cation. Predictive Selection Rules
  作者：Do Hyun Ryu、Gang Zhou、E. J. Corey

  DOI：10.1021/ja049323b

  日期：2004.4.1

  The chiral oxazaborolidinium cation 1 promotes Diels-Alder reactions between 2-triisopropylsilyloxy-1,3-butadiene and a number of unsymmetrical 1,4-benzoquinones in a highly enantioselective and structurally selective manner. The basis for the enantioselectivity is explained rationally in terms of a preferred type of transition-state assembly. Selection rules have been developed that allow the prediction of the principal reaction product of Diels-Alder reaction between unsymmetrical diene and quinone components.