(1S,1'R)-1-[2,2,2-trifluoro-1-(1-naphth-1-ylethylamino)ethyl]naphth-2-ol | 402617-59-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1S,1'R)-1-[2,2,2-trifluoro-1-(1-naphth-1-ylethylamino)ethyl]naphth-2-ol
• 英文别名: 1-[(1S)-2,2,2-trifluoro-1-[[(1R)-1-naphthalen-1-ylethyl]amino]ethyl]naphthalen-2-ol
• CAS: 402617-59-8
• 化学式: C₂₄H₂₀F₃NO
• 分子量: 395.424
• InChiKey: KTDMFQUXQHPPOG-CMJOXMDJSA-N

物化性质

• 沸点：
  509.3±50.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,1'R)-1-[2,2,2-trifluoro-1-(1-naphth-1-ylethylamino)ethyl]naphth-2-ol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以72%的产率得到(S)-1-(1-amino-2,2,2-trifluoroethyl)naphthalen-2-ol
  参考文献：
  名称：

  Diastereoselective Friedel–Crafts reaction of α-trifluoromethyl imines derived from chiral amines

  摘要：

  The Friedel-Crafts reactions of chiral N-(2,2,2-trifluoroethylidene)-1-arylethylamines 1a and 1b with various electron-rich aromatic compounds were examined. The reactions proceeded readily at room temperature in the presence of BF3.Et2O. Substituted products 2-12 were obtained in low to very high stereo selectivities (up to 100% d.e.). The absolute configuration of compound 12 was determined by X-ray analysis. Moreover, the chiral auxiliary from compounds 3 and 12 was selectively removed by palladium-catalyzed hydrogenolysis. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00402-5
• 作为产物：
  描述：

  (R)-1-(1-萘基)乙胺 在 4 A molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 50.0h， 生成 (1S,1'R)-1-[2,2,2-trifluoro-1-(1-naphth-1-ylethylamino)ethyl]naphth-2-ol
  参考文献：
  名称：

  Diastereoselective Friedel–Crafts reaction of α-trifluoromethyl imines derived from chiral amines

  摘要：

  The Friedel-Crafts reactions of chiral N-(2,2,2-trifluoroethylidene)-1-arylethylamines 1a and 1b with various electron-rich aromatic compounds were examined. The reactions proceeded readily at room temperature in the presence of BF3.Et2O. Substituted products 2-12 were obtained in low to very high stereo selectivities (up to 100% d.e.). The absolute configuration of compound 12 was determined by X-ray analysis. Moreover, the chiral auxiliary from compounds 3 and 12 was selectively removed by palladium-catalyzed hydrogenolysis. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00402-5

文献信息

• Diastereoselective Friedel–Crafts reaction of α-trifluoromethyl imines derived from chiral amines
  作者：Yuefa Gong、Katsuya Kato

  DOI：10.1016/s0957-4166(01)00402-5

  日期：2001.8

  The Friedel-Crafts reactions of chiral N-(2,2,2-trifluoroethylidene)-1-arylethylamines 1a and 1b with various electron-rich aromatic compounds were examined. The reactions proceeded readily at room temperature in the presence of BF3.Et2O. Substituted products 2-12 were obtained in low to very high stereo selectivities (up to 100% d.e.). The absolute configuration of compound 12 was determined by X-ray analysis. Moreover, the chiral auxiliary from compounds 3 and 12 was selectively removed by palladium-catalyzed hydrogenolysis. (C) 2001 Elsevier Science Ltd. All rights reserved.