(1S,2R)-2-(1-naphthyl)cyclohexanol | 157604-38-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1S,2R)-2-(1-naphthyl)cyclohexanol
• 英文别名: (1S,2R)-trans-2-(1-naphthyl)-1-cyclohexanol；trans-2-(naphthalen-1-yl)cyclohexan-1-ol；(1S,2R)-2-naphthalen-1-ylcyclohexan-1-ol
• CAS: 157604-38-1
• 化学式: C₁₆H₁₈O
• 分子量: 226.318
• InChiKey: GLPLBZSYNMNCEQ-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  (+/-)-trans-2-(1-naphthyl)cyclohexanol 以49.9%的产率得到(1S,2R)-2-(1-naphthyl)cyclohexanol
  参考文献：
  名称：

  Preparation of enantiomerically pure trans- and cis-2-(1-naphthyl)cyclohexan-1-ols

  摘要：

  Lipase-mediated treatment of racemic trans-2-(1-naphthyl)cyclohexan-1-ol with vinyl acetate allows clear-cut enantiospecific kinetic acetylation to give (+)-(1R,2S)-acetate in excellent chemical and enantiomeric excesses leaving (+)-(1S,2R)-alcohol in an excellent enantiomeric purity and excellent recovery. The enantiomerically pure alcohol obtained is transformed into the diastereomeric alcohol neatly via the Mitsunobu inversion reaction.

  DOI：

  10.1016/0957-4166(95)00206-5

文献信息

• 一种手性反式2-取代环烷醇的合成方法
  申请人：中国科学院大连化学物理研究所

  公开号：CN113354515A

  公开（公告）日：2021-09-07

  一种手性反式2‑取代环烷醇的合成方法。本发明提供了一种钯催化2‑取代环酮的不对称氢化合成手性反式环烷醇的方法，所述方法以金属钯的手性双膦P‑P*配合物为催化剂，配合使用酸添加剂，对2‑取代环酮化合物进行不对称氢化，得到相应的手性反式环烷醇化合物，其对映体过量最多可达到97％，反式选择性高达20:1。本发明操作简便实用易行，收率高，高原子经济性和环境友好型，催化剂商业可得，反应条件温和，具有潜在的实际应用价值。
• Organolithium/Chiral Lewis Base/BF3: a Versatile Combination for the Enantioselective Desymmetrization ofmeso-Epoxides
  作者：Emmanuel Vrancken、Alexandre Alexakis、Pierre Mangeney

  DOI：10.1002/ejoc.200400745

  日期：2005.4

  BF3 can be used in combination with organolithium/strong Lewis base complexes for the enantioselective nucleophilic ring-opening or the carbenoidic rearrangement of various meso-oxiranes with excellent yields and ee values of up to 87 %. Mechanistic aspects of these reactions are considered.

  BF3 可与有机锂/强路易斯碱配合物结合使用，用于对映选择性亲核开环或各种内消旋环氧乙烷的碳烯重排，收率高，ee 值高达 87%。考虑了这些反应的机械方面。
• Enantioselective Nucleophilic Opening of <i>meso</i> Epoxides by Organolithium Reagents
  作者：Alexandre Alexakis、Emmanuel Vrancken、Pierre Mangeney

  DOI：10.1055/s-1998-5741

  日期：1998.10

  Aryl lithium reagents, complexed with (-)-sparteine, react enantioselectively with cyclic meso epoxides, to afford chiral aryl cyclanols. The enantiomeric excess, though moderate (27-87%), is the best in the literature for such a reaction. Activation by BF3 · OEt2 is needed, and is compatible with a diamine such as (-)-sparteine.

  芳基锂试剂与 (-)-sparteine 络合，与环状内消旋环氧化物对映选择性反应，得到手性芳基环醇。对映体过量虽然适中 (27-87%)，但在此类反应的文献中是最好的。需要 BF3·OEt2 活化，并且与二胺如 (-)-sparteine 相容。
• Palladium-catalyzed asymmetric hydrogenation of 2-aryl cyclic ketones for the synthesis of <i>trans</i> cycloalkanols through dynamic kinetic resolution under acidic conditions
  作者：Xiang Li、Zi-Biao Zhao、Mu-Wang Chen、Bo Wu、Han Wang、Chang-Bin Yu、Yong-Gui Zhou

  DOI：10.1039/d0cc00480d

  日期：——

  The first efficient palladium-catalyzed asymmetric hydrogenation of 2-aryl cyclic ketones has been described through dynamic kinetic resolution under acidic conditions, providing a facile access to chiral trans cycloalkanol derivatives with excellent enantioselectivities.

  已经通过在酸性条件下的动态动力学拆分描述了第一个有效的钯催化的2-芳基环酮的不对称加氢反应，提供了容易获得的具有优异对映选择性的手性反式环烷醇衍生物的方法。
• Diastereoselective and Enantioselective Silylation of 2-Arylcyclohexanols
  作者：Li Wang、Ravish K. Akhani、Sheryl L. Wiskur

  DOI：10.1021/acs.orglett.5b00919

  日期：2015.5.15

  The silylation-based kinetic resolution of trans 2-arylcyclohexanols was accomplished by employing a triaryl silyl chloride as the derivatizing reagent with a commercially available isothiourea catalyst. The methodology is selective for the trans diastereomer over the cis, which provides an opportunity to selectively derivatize one stereoisomer out of a mixture of four. By employing this technology, a facile, convenient method to form a highly enantiomerically enriched silylated alcohol was accomplished through a one-pot reduction-silylation sequence that started with a 2-aryl-substituted ketone.