(4aS,8aR)-4a,5,8,8a-tetrahydro-2-bromo-7-(triisopropylsilyl)oxy-8a-methylnaphthalene-1,4-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aS,8aR)-4a,5,8,8a-tetrahydro-2-bromo-7-(triisopropylsilyl)oxy-8a-methylnaphthalene-1,4-dione
• 英文别名: (4aS,8aR)-2-bromo-8a-methyl-7-tri(propan-2-yl)silyloxy-5,8-dihydro-4aH-naphthalene-1,4-dione
• 化学式: C₂₀H₃₁BrO₃Si
• 分子量: 427.454
• InChiKey: BEBWFJVXNBXHSG-OXQOHEQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.91
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴-6-甲基-p-苯醌 、 2-(triisopropylsiloxy)-1,3-butadiene 在 oxazaborolidinium⁽¹⁺⁾*Tf₂N^(1-) 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (4aR,8aS)-4a,5,8,8a-tetrahydro-2-bromo-7-(triisopropylsilyl)oxy-8a-methylnaphthalene-1,4-dione 、 (4aS,8aR)-4a,5,8,8a-tetrahydro-2-bromo-7-(triisopropylsilyl)oxy-8a-methylnaphthalene-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.