(1S)-1-(3-cyclohexenyl)propanol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S)-1-(3-cyclohexenyl)propanol
• 英文别名: (1S)-1-cyclohex-3-en-1-ylpropan-1-ol
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: AEQGOXXJTSQAAV-GKAPJAKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  diethylzinc 、 3-环己烯甲醛 在 (R)-(-)-2-哌啶-1,1,2-三苯基乙醇 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 3.0h， 生成 (1S)-1-(3-cyclohexenyl)propanol
  参考文献：
  名称：

  一种优良的，易于获得的对映纯配体，用于将二乙基锌催化α-取代的醛对映选择性加成。

  摘要：

  高氯酸锂诱导的（S）-三苯基环氧乙烷（3）与仲胺（哌啶（a），N-甲基哌嗪（b），N-苯基哌嗪（c）和吗啉（d））的开环反应以立体定向方式进行并以完全区域选择性的方式得到（R）-2-（二烷基氨基）-1,1,2-三苯乙醇（4a-d）。这些氨基醇在0℃和室温下以高对映选择性催化诱导二乙基锌加至苯甲醛中。在将Et（2）Zn添加到20个代表性的脂族和芳族醛5a-t族中时，已经研究了在0摄氏度下提供最高对映选择性的配体4a。对于17个成员组成的一组α-取代的底物（5a-m，qt），包括邻，间和对位取代的苯甲醛，萘醛，

  DOI：

  10.1021/jo981336i

文献信息

• A Superior, Readily Available Enantiopure Ligand for the Catalytic Enantioselective Addition of Diethylzinc to α-Substituted Aldehydes
  作者：Lluís Solà、Katamreddy Subba Reddy、Anton Vidal-Ferran、Albert Moyano、Miquel A. Pericàs、Antoni Riera、Angel Alvarez-Larena、Joan-F. Piniella

  DOI：10.1021/jo981336i

  日期：1998.10.1

  2-triphenylethanols (4a-d). These amino alcohols catalytically induce the addition of diethylzinc to benzaldehyde with high enantioselectivity at 0 degrees C and at room temperature. Ligand 4a, which provides the highest enantioselectivity at 0 degrees C, has been studied in the addition of Et(2)Zn to a family of 20 representative aliphatic and aromatic aldehydes 5a-t. For a 17-membered set of alpha-substituted

  高氯酸锂诱导的（S）-三苯基环氧乙烷（3）与仲胺（哌啶（a），N-甲基哌嗪（b），N-苯基哌嗪（c）和吗啉（d））的开环反应以立体定向方式进行并以完全区域选择性的方式得到（R）-2-（二烷基氨基）-1,1,2-三苯乙醇（4a-d）。这些氨基醇在0℃和室温下以高对映选择性催化诱导二乙基锌加至苯甲醛中。在将Et（2）Zn添加到20个代表性的脂族和芳族醛5a-t族中时，已经研究了在0摄氏度下提供最高对映选择性的配体4a。对于17个成员组成的一组α-取代的底物（5a-m，qt），包括邻，间和对位取代的苯甲醛，萘醛，
• High Catalytic Activity of Chiral Amino Alcohol Ligands Anchored to Polystyrene Resins
  作者：Anton Vidal-Ferran、Nick Bampos、Albert Moyano、Miquel A. Pericàs、Antoni Riera、Jeremy K. M. Sanders

  DOI：10.1021/jo980708k

  日期：1998.9.1

  Enantiomerically pure (2S,3S)-2,3-epoxy-3-phenylpropanol (3) has been anchored to Merrifield resins with different degrees of cross-linking and functionalization. The resulting epoxy-functionalized resins 4 have been submitted to completely regioselective (C-3 attack) and stereospecific ring-opening with secondary amines [piperidine (a), N-methylpiperazine (b), and cis-2,6-dimethylpiperidine (c)] in the presence of lithium perchlorate to afford (2R,3R)-3-(dialkylamino)-2-hydroxy-3-phenylpropoxy resin ethers 5a-c. The progress of these two processes has been monitored by C-13 gel-phase NMR spectroscopy. Polymer-supported amino alcohols 5a-c have been evaluated as catalytic ligands in the enantioselective addition of diethylzinc to benzaldehyde, best results being obtained with the cis-2,6-dimethylpiperidine containing ligand 5c. Analogously, (2R,3R)-3-(cis-2,6-dimethylpiperidino)-3-phenyl-1,2-propanediol (11) has been anchored to a 2-chlorotrityl chloride resin (Barlos resin) in dichloromethane in the presence of diisopropylethylamine, and the anchoring process has been also monitored by C-13 gel-phase NMR spectroscopy. The resulting resin 12 has subsequently been used as a chiral ligand in the catalytic addition at 0 degrees C of diethylzinc to a family of fourteen representative aromatic and aliphatic aldehydes 8a-n, to afford the corresponding (S)-1-substituted 1-propanols 10a-n with a mean enantiomeric excess of 92%.