(R)-2-ethyl-2-hydroxy-1-tetralone | 124867-62-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (R)-2-ethyl-2-hydroxy-1-tetralone
• 英文别名: (2R)-2-ethyl-2-hydroxy-3,4-dihydronaphthalen-1-one
• CAS: 124867-62-5
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: RJODYSFGGBOLHJ-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-hydroxy-1-tetralone dimethyl ketal 在 盐酸 、 重铬酸吡啶 、 molecular sieve 、 乙酸酐 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.17h， 生成 (R)-2-ethyl-2-hydroxy-1-tetralone
  参考文献：
  名称：

  Fujioka, Hiromichi; Kondo, Hiroshi; Annoura, Hirokazu, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 6, p. 1488 - 1492

  摘要：

  DOI：

文献信息

• Monodeazacinchona Alkaloid Derivatives: Synthesis and Preliminary Applications as Phase-Transfer Catalysts
  作者：Eckehard Volker Dehmlow、Stephanie Düttmann、Beate Neumann、Hans-Georg Stammler

  DOI：10.1002/1099-0690(200207)2002:13<2087::aid-ejoc2087>3.0.co;2-z

  日期：2002.7

  alkaloids (5−8) lacking the quinoline nitrogen atom have been prepared. Quaternization afforded the phase-transfer catalysts 10a, 10b, 11a, and 12d. Other optically active catalyst salts were prepared from the cinchona alkaloids themselves (compounds 13, 14, 15). The performances of these PT catalysts and of some others were compared in three test reactions. The deazacinchona derivatives exhibited selectivities

  已经制备了四种缺乏喹啉氮原子的金鸡纳生物碱 (5-8) 类似物。季铵化得到相转移催化剂10a、10b、11a和12d。其他光学活性催化剂盐是由金鸡纳生物碱本身（化合物 13、14、15）制备的。在三个测试反应中比较了这些 PT 催化剂和其他一些催化剂的性能。去氮杂金鸡纳衍生物表现出与天然产物衍生化合物相似或有时甚至更好的选择性。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
• New methods and reagents in organic synthesis. 75. asymmetric synthesis of α-hydroxy ketones using chiral phase transfer catalysts
  作者：Moriyasu Masui、Akira Ando、Takayuki Shioiri

  DOI：10.1016/0040-4039(88)85224-9

  日期：——

  Optically active α-hydroxy ketones are obtained by oxidation of achiral ketones with molecular oxygen in two phase system using chiral phase transfer catalysts.

  光学活性α-羟基酮是通过使用手性相转移催化剂在两相体系中用分子氧将非手性酮氧化而获得的。
• Enantioselective PTC: Varying the cinchona alkaloid motive
  作者：Eckehard Volker Dehmlow、Stefan Wagner、Achim Müller

  DOI：10.1016/s0040-4020(99)00210-0

  日期：1999.5

  Enantiopure phase transfer catalysts 3a-j, 4a-j, 5, 8a-j, 9a,b, 10a,b were prepared which represent changes in the fundamental structure of the alkaloids. These were tested in three enantioselective model reactions. It turned out that both the quinoline group carrying side arm and the quinuclidine core are important features of PT catalysts for highly enantioselective reactions. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Asymmetric Intramolecular Crossed-Benzoin Reactions by N-Heterocyclic Carbene Catalysis
  作者：Dieter Enders、Oliver Niemeier、Tim Balensiefer

  DOI：10.1002/anie.200503885

  日期：2006.2.20
• Enantioselective oxidation of aromatic ketones by molecular oxygen, catalyzed by chiral monoaza-crown ethers
  作者：Erik F.J. de Vries、Lisette Ploeg、Marcello Colao、Johannes Brussee、Arne van der Gen

  DOI：10.1016/0957-4166(95)00138-f

  日期：1995.5

  Chiral monoaza-15-crown-5 ethers 3a-c and monoaza-18-crown-6 ethers 3d-f have been synthesized from optically active diethanolamines in moderate to good yields. One of these crown ethers, i.e. 3a, proved to be both an efficient and a selective phase transfer catalyst in the asymmetric oxidation of aromatic ketones:by molecular oxygen. Yields of the oxidation reaction were high and enantiomeric ! excesses of up to 72% could be obtained. To account for the remarkable differences in asymmetric induction between the crown ethers tested, a model for the:structure of the transition stare was proposed.