(R,R)-di[1-(9-anthryl)-2,2,2-trifluoroethyl]fumarate | 929108-81-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (R,R)-di[1-(9-anthryl)-2,2,2-trifluoroethyl]fumarate
• 英文别名: bis[(1R)-1-anthracen-9-yl-2,2,2-trifluoroethyl] (E)-but-2-enedioate
• CAS: 929108-81-6
• 化学式: C₃₆H₂₂F₆O₄
• 分子量: 632.559
• InChiKey: UMDVXEXVTHKYLK-PTKCYFMJSA-N

物化性质

• 沸点：
  700.5±60.0 °C(Predicted)
• 密度：
  1.395±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  46
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (R,R)-di[1-(9-anthryl)-2,2,2-trifluoroethyl]fumarate 在 lithium aluminium tetrahydride 、 二氯乙基铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (R)-(-)-1-(9-蒽基)-2,2,2-三氟乙醇
  参考文献：
  名称：

  Di-2,2,2-trifluoro-1-(9-anthryl)ethyl fumarate, an easy starting point for the enantioselective preparation of trans-cyclohexene-4,5-dicarboxylate derivatives by Diels–Alder reaction

  摘要：

  Di-2,2,2-trifluoro-1-(9-anthryl)ethyl fumarate has been synthesized from fumaric acid and enantiopure Pirkle alcohol. The Diels-Alder reaction with different dienes employing different reaction conditions was assayed, with high diastereomeric excesses obtained. The structure and geometry of the cycloadducts was analyzed by NMR, molecular mechanics and X-ray diffraction. Hydrolysis made it possible to obtain the enantioenriched trans-cyclohexene-4,5-dicarboxylate derivatives and allow us to recover chiral auxiliary. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.047
• 作为产物：
  描述：

  bis[(1R)-1-anthracen-9-yl-2,2,2-trifluoroethyl] (1R,2S,3S,4S)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate 在 4-二甲氨基吡啶 、 氢氧化钾 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 (R,R)-di[1-(9-anthryl)-2,2,2-trifluoroethyl]fumarate
  参考文献：
  名称：

  Di-2,2,2-trifluoro-1-(9-anthryl)ethyl fumarate, an easy starting point for the enantioselective preparation of trans-cyclohexene-4,5-dicarboxylate derivatives by Diels–Alder reaction

  摘要：

  Di-2,2,2-trifluoro-1-(9-anthryl)ethyl fumarate has been synthesized from fumaric acid and enantiopure Pirkle alcohol. The Diels-Alder reaction with different dienes employing different reaction conditions was assayed, with high diastereomeric excesses obtained. The structure and geometry of the cycloadducts was analyzed by NMR, molecular mechanics and X-ray diffraction. Hydrolysis made it possible to obtain the enantioenriched trans-cyclohexene-4,5-dicarboxylate derivatives and allow us to recover chiral auxiliary. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.11.047