2,3,4a-trimethyl-1,4,4a,9a-tetrahydro-anthraquinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2,3,4a-trimethyl-1,4,4a,9a-tetrahydro-anthraquinone
• 英文别名: (4aR,9aS)-2,3,9a-trimethyl-4,4a-dihydro-1H-anthracene-9,10-dione
• 化学式: C₁₇H₁₈O₂
• 分子量: 254.329
• InChiKey: PHTYAJGFDHELTH-YOEHRIQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  2,3,4a-trimethyl-1,4,4a,9a-tetrahydro-anthraquinone 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 以92%的产率得到(4aα,9aβ,10β)-1,4,4a,9a,10-pentahydro-10-hydroxy-2,3,4a-trimethylanthracen-9-one
  参考文献：
  名称：

  NaBH 4 / CeCl 3还原环状二烯的区域选择性

  摘要：

  在有和没有氯化铈（III）的情况下，硼氢化钠对环状二烯的还原反应在区域化学偏好上有着明显的不同。在存在CeCl 3的情况下，还原作用似乎受两个现象控制：与没有CeCl 3的反应相同，轴向加成的可及性和路易斯酸络合的可及性。

  DOI：

  10.1016/s0040-4039(97)01498-6
• 作为产物：
  描述：

  甲萘醌 、 2,3-二甲基-1,3-丁二烯 生成 2,3,4a-trimethyl-1,4,4a,9a-tetrahydro-anthraquinone
  参考文献：
  名称：

  Regio- and Stereoselectivity in the Reductions of Cyclic Enedione Systems

  摘要：

  Reductions of cyclic enedione substrates by NaBH4 and by LiAl(O-t-Bu)(3)H very predominantly gave monoreduction products with very high regio- and stereoselectivity. The reductions involved axial delivery of the hydride. The results indicated that electronic factors were dominated by steric considerations in the transition state of the reduction, even though the seemingly more encumbered carbonyl was reduced.

  DOI：

  10.1021/jo962377m

文献信息

• Rate Enhancement of Diels−Alder Reactions in Aqueous Perfluorinated Emulsions
  作者：Kohsuke Nishimoto、Shokaku Kim、Yoshikazu Kitano、Masahiro Tada、Kazuhiro Chiba

  DOI：10.1021/ol0623116

  日期：2006.11.1

  A marked acceleration property for the Diels-Alder reaction was observed in an aqueous micellar system composed of perfluorohexane and lithium perfluorooctanesulfonate. The reaction rate increased with the concentration of the equimolar mixture of PFH and LiFOS, and the rate in 500 mM PFH and 500 mM LiFOS was about 100-fold greater than that in water without the fluorous field. After completion of the reaction, the products were simply extracted from the aqueous reaction mixture using n-hexane.