(4aS,9aR)-1,4,4a,9a-tetrahydro-2-(triisopropylsilyl)oxy-9a-methylanthracene-9,10-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (4aS,9aR)-1,4,4a,9a-tetrahydro-2-(triisopropylsilyl)oxy-9a-methylanthracene-9,10-dione
• 英文别名: (4aS,9aR)-9a-methyl-2-tri(propan-2-yl)silyloxy-4,4a-dihydro-1H-anthracene-9,10-dione
• 化学式: C₂₄H₃₄O₃Si
• 分子量: 398.618
• InChiKey: YNGRLZNEBLOQKY-ZJSXRUAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.56
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 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：

  (4aS,9aR)-1,4,4a,9a-tetrahydro-2-(triisopropylsilyl)oxy-9a-methylanthracene-9,10-dione 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (4aS,9R,9aR)-1,4,4a,9a-tetrahydro-9-hydroxy-2-(triisopropylsilyl)oxy-9a-methylanthracen-10(9H)-one
  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：

  甲萘醌 、 2-(triisopropylsiloxy)-1,3-butadiene 在 oxazaborolidinium⁽¹⁺⁾*Tf₂N^(1-) 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 生成 (4aR,9aS)-1,4,4a,9a-tetrahydro-2-(triisopropylsilyl)oxy-9a-methylanthracene-9,10-dione 、 (4aS,9aR)-1,4,4a,9a-tetrahydro-2-(triisopropylsilyl)oxy-9a-methylanthracene-9,10-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.