(S)-1-(9-anthryl)propan-1-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (S)-1-(9-anthryl)propan-1-ol
• 英文别名: (S)-1-(9-phenanthryl)propan-1-ol；(S)-(-)-1-(9-anthryl)-1-propanol；(S)-1-(9-anthracyl)-1-propanol；(S)-1-(9-anthracy)-1-propanol；1-(9-anthryl)propan-1-ol；(1S)-1-anthracen-9-ylpropan-1-ol
• 化学式: C₁₇H₁₆O
• 分子量: 236.313
• InChiKey: GNDCPGDIHGSTNN-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  三乙基铝 、 9-蒽甲醛 在 titanium(IV) isopropylate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 24.25h， 以85%的产率得到
  参考文献：
  名称：

  Preparation of several BINOL-based polymeric ligands for the enantioselective addition of triethylaluminium to aromatic aldehydes

  摘要：

  The synthesis of several polystyrene-supported BINOL (1,1-binaphthol) ligands via radical polymerization is described. These BINOL-based polymeric ligands were applied to the enantioselective addition of triethylaluminium to aromatic aldehyde in the presence of titanium isopropoxide. The products were obtained with up to 93% enantiomeric excess (ee) in good to excellent yield. The ligands were easily recovered and reused without losing their catalytic activity as well as enantioselectivity. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.12.076

文献信息

• New polymer anchored chiral amino oxazolines as effective catalysts for enantioselective addition of diethylzinc to aldehydes
  作者：Nadim S Shaikh、Vishnu H Deshpande、Ashutosh V Bedekar

  DOI：10.1016/s0040-4039(02)01139-5

  日期：2002.8

  The application of a new type of polymer anchored chiral amino-oxazolinyl ligand as catalyst for the enantioselective addition of diethylzinc to aldehydes is reported. The catalyst is effective at a low ligand concentration and can be reused with minimal loss of activity.

  报道了一种新型的聚合物锚定的手性氨基-恶唑啉基配体作为催化剂将二乙基锌对醛进行对映选择性加成的报道。该催化剂在低配体浓度下是有效的，并且可以在活性损失最小的情况下重复使用。
• A Catalytic and Mechanistic Investigation of Optically Active Helical Poly[3-(9-alkylfluoren-9-yl)propylene oxide]s in the Enantioselective Addition of Ethylmagnesium Bromide to Aldehydes
  作者：Anlin Zhang、Nianfa Yang、Liwen Yang、Dan Peng

  DOI：10.1246/cl.131101

  日期：2014.4.5

  Optically active helical poly[(S)-3-(9-alkylfluoren-9-yl)propylene oxide]s (poly-(S)-AFPOs) without additional stereogenic units were used to induce the enantioselective addition of ethylmagnesium bromide to aldehydes, giving up to 53% ee of the products. It is the helically chiral environment rather than the point chirality that governs the enantioselective inducement of the addition reaction. Poly-(S)-AFPOs could be recovered simply, post-treated conveniently and used repeatedly.

  光学活性的螺旋聚[(S)-3-(9-烷基芴-9-基)丙烯氧化物]（聚-(S)-AFPOs）在没有额外立体中心的情况下用于诱导乙基溴化镁对醛的选择性加成，产物的对映体过量可达53%。在该加成反应的选择性诱导中，主导因素是螺旋手性环境而非点手性。聚-(S)-AFPOs可以简单回收，方便后处理并可重复使用。
• A practical o-hydroxybenzylamines promoted enantioselective addition of dialkylzincs to aldehydes with asymmetric amplification
  作者：Gianni Palmieri

  DOI：10.1016/s0957-4166(00)00290-1

  日期：2000.8

  The addition of dialkylzincs to aldehydes is accelerated considerably by the presence of a catalytic amount of o-hydroxybenzylamine (R,R)-2e to give, after hydrolysis, the corresponding alcohol (S)-9 in good enantiomeric purity. The origins of the enantioselection have been elucidated. A strong positive nonlinear relationship was observed for the reaction enantioselectivity with the use of o-hydroxybenzylamine 2e, which is very accessible through a short stereoselective synthetic route. The enantiomeric purity of the product 9 is much higher than the d.e. of the chiral source 2e, and the rate of the enantioselective catalysis increases considerably with the increase of the d.e. of(R,R)-2e. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Catalytic asymmetric induction Part 2. Chiral tricarbonyl (η6 arene) chromium (0) complexes as enantioselective catalysts
  作者：Graham B. Jones、Steven B. Heaton

  DOI：10.1016/s0957-4166(00)82346-0

  日期：1993.2

  A chiral metallocyclic Lewis acid based catalyst system derived from norephedrine is reported. A key stereodirective element emanates from a tricarbonyl chromium (0) group complexed to the aryl ring. The catalysts mediate the addition of dialkyl zinc species to a variety of aldehydes with high enantioselectivity.
• 1,1′-Binaphthylazepine-based ligands for asymmetric catalysis. Part 2: New aminoalcohols as chiral ligands in the enantioselective addition of ZnEt2 to aromatic aldehydes
  作者：Stefano Superchi、Tommaso Mecca、Egidio Giorgio、Carlo Rosini

  DOI：10.1016/s0957-4166(01)00200-2

  日期：2001.5

  The new enantiopure 1,2-aminoalcohols 1b-1h having 1,1 ' -binaphthylazepine skeleton have been tested as catalytic precursors in the enantioselective addition of ZnEt2 to benzaldehyde. The best results were seen with ligand 1d, which owes its chirality only to the atropisomerism of the binaphthyl nucleus and does not have any stereogenic carbon atom. In the presence of 1d benzaldehyde was quickly and cleanly transformed to (S)-1-phenylpropanol in 99% yield and 87% e.e. The same ligand was also used in the asymmetric ZnEt2 addition to other aryl aldehydes giving rise to (S)-1-arylpropanols in almost quantitative yields and e.e.s up to 90%. (C) 2001 Elsevier Science Ltd. All rights reserved.