(4aR,8aS)-2,3,6-trimethyl-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone | 548786-38-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aR,8aS)-2,3,6-trimethyl-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone
• 英文别名: (4aR,8aS)-2,3,6-trimethyl-4a,5,8,8a-tetrahydronaphthalene-1,4-dione
• CAS: 548786-38-5
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: SIVIRSQBJWMAEN-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4aR,8aS)-2,3,6-trimethyl-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone 在 sodium tetrahydroborate 、 cerium(III) chloride 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 甲醇 、 四氢呋喃 为溶剂， 反应 5.0h， 以40%的产率得到(1S,2S,4S,8R,9R)-2-bromo-1,6,7-trimethyl-11-oxa-tricyclo[6,2,1,0^4,9]undec-6-en-5-one
  参考文献：
  名称：

  Triflimide Activation of a Chiral Oxazaborolidine Leads to a More General Catalytic System for Enantioselective Diels−Alder Addition

  摘要：

  The strong acid triflimide ((CF3SO2)2NH) protonates chiral oxazaborolidines to form superactive, stable, chiral Lewis acids which are highly effective catalysts for a wide variety of enantioselective Diels-Alder reactions, documented herein by more than 20 examples.

  DOI：

  10.1021/ja035393r
• 作为产物：
  描述：

  2,3-二甲基-1,4-苯醌 、 天然橡胶 在 triflimide activated chiral oxazaborolidine 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (4aR,8aS)-2,3,6-trimethyl-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone 、 (4aS,8aR)-2,3,6-trimethyl-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone
  参考文献：
  名称：

  Triflimide Activation of a Chiral Oxazaborolidine Leads to a More General Catalytic System for Enantioselective Diels−Alder Addition

  摘要：

  The strong acid triflimide ((CF3SO2)2NH) protonates chiral oxazaborolidines to form superactive, stable, chiral Lewis acids which are highly effective catalysts for a wide variety of enantioselective Diels-Alder reactions, documented herein by more than 20 examples.

  DOI：

  10.1021/ja035393r

文献信息

• Triflimide Activation of a Chiral Oxazaborolidine Leads to a More General Catalytic System for Enantioselective Diels−Alder Addition
  作者：Do Hyun Ryu、E. J. Corey

  DOI：10.1021/ja035393r

  日期：2003.5.1

  The strong acid triflimide ((CF3SO2)2NH) protonates chiral oxazaborolidines to form superactive, stable, chiral Lewis acids which are highly effective catalysts for a wide variety of enantioselective Diels-Alder reactions, documented herein by more than 20 examples.