4-Bromo-benzoic acid (1S,3R,6S,7R,8S)-1-triisopropylsilanyloxy-2-oxa-tricyclo[5.3.1.03,8]undec-4-en-6-yl ester | 691391-08-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-Bromo-benzoic acid (1S,3R,6S,7R,8S)-1-triisopropylsilanyloxy-2-oxa-tricyclo[5.3.1.03,8]undec-4-en-6-yl ester
• 英文别名: 4-Bromo-benzoic acid (1S,3R,6S,7R,8S)-1-triisopropylsilanyloxy-2-oxa-tricyclo[5.3.1.0^3,8]undec-4-en-6-yl ester
• CAS: 691391-08-9
• 化学式: C₂₆H₃₇BrO₄Si
• 分子量: 521.567
• InChiKey: SSKOXZPDHDQNDA-YBTKJZEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.25
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-Bromo-benzoic acid (1S,3R,6S,7R,8S)-1-triisopropylsilanyloxy-2-oxa-tricyclo[5.3.1.03,8]undec-4-en-6-yl ester 在 氢氟酸 作用下， 以 乙腈 为溶剂， 生成 (1R,4S,4aR,8aS)-1,4,4a,5,6,7,8,8a-octahydro-1-hydroxy-6-oxonaphthalen-4-yl-4-bromobenzoate
  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：

  (1R,4S,4aR,8aS)-1,4,4a,5,8,8a-hexahydro-6-(triisopropylsilyl)oxynaphthalene-1,4-diol 在 吡啶 、 4-二甲氨基吡啶 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 4-Bromo-benzoic acid (1S,3R,6S,7R,8S)-1-triisopropylsilanyloxy-2-oxa-tricyclo[5.3.1.03,8]undec-4-en-6-yl ester
  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