trans-(2-hydroxycyclohexyl)quinoline | 3297-66-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: trans-(2-hydroxycyclohexyl)quinoline
• 英文别名: (+/-)-trans-2-quinolin-2-ylcyclohexanol；(±)-trans-2-(quinolin-2-yl)cyclohexanol；(1R,2S)-2-quinolin-2-ylcyclohexan-1-ol
• CAS: 3297-66-3
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: NWPDRICMNYXUBU-SWLSCSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  trans-(2-hydroxycyclohexyl)quinoline 在 (S)-(+)-扁桃酸 、 三乙胺 、 4,5-二氯咪唑 作用下， 以 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 [(1S,2R)-trans-2-(quinolin-2-yl)cyclohexan-1-oxy]diphenyl phosphine
  参考文献：
  名称：

  Improved Synthesis of Cyclohexane-Backbone Iridium-Complexes of Quinoline-Phosphine and Their Applications in Asymmetric Hydrogenation

  摘要：

  The iridium-complexes 3 and 4 with cyclohexane-backbone derived from quinoline were easily synthesized. The key step is cis/trans stereoselective reduction of 2-(quinolin-2-yl)cyclohexanone 5 to trans-2-(quinolin-2-yl)cyclohexanol 6 using Al(Oi-Pr)(3)/i-PrOH and the following diastereomeric optical resolution of racemic 6 using 0.50 equiv (S)-mandelic acid in EtOAc. These complexes were used in the asymmetric hydrogenation of (E)-1,2-diphenylpropene with up to 13% ee/48% cony. using 3 and 35% ee/9% cony. using 4. For the hydrogenation of (2H-chromen-3-yl)methanol, up to 80% ee/95% yield and 72% ee/96% yield were achieved. The same configuration of the products by using 3 and 4 suggested that the absolute configuration was controlled by the configuration of the stereogenic quinolinyl-bearing carbon of the complexes.

  DOI：

  10.3987/com-20-14284
• 作为产物：
  描述：

  2-(quinolin-2-yl)cyclohexanone 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 3.5h， 生成 trans-(2-hydroxycyclohexyl)quinoline
  参考文献：
  名称：

  1 H NMR通过其非对映异构体测定1-或2-芳基取代的醇和胺的绝对构型：通过萃取分离吡啶醇的非对映异构体衍生物的新型分离技术。

  摘要：

  实现了确定反式-2-芳基环己醇，1-芳基醇和胺的绝对构型的简便方法。该方法利用了1H NMR光谱观察到的由芳族屏蔽效应引起的C18-CH3质子显着的高场位移。它基于对衍生自3β-乙酰氧基-5-乙烯酸的两种非对映异构体中环境差异的区分。此外，观察到，基于其碱性的差异，通过萃取简单地分离了吡啶醇的相应的非对映异构衍生物。

  DOI：

  10.1002/1521-3765(20021216)8:24<5551::aid-chem5551>3.0.co;2-v

文献信息

• Synthesis of Chiral P,N-ligands derived from Quinoline and their Application in Asymmetric Allylic Alkylations
  作者：Yan-Hong Shen、Hui-Chao Lv、Liang Zhao

  DOI：10.3184/174751911x13082269792294

  日期：2011.6

  Chiral P,N-ligands derived from quinoline and with a trans and cis cyclohexane backbone were easily synthesised in four steps from quinoline N-oxide. The enantiopure trans isomer was obtained by the way of chiral resolution of the mixture of trans- and cis-2-(quinolin-2-yl)cyclohexanol with dibenzoyltartaric acid and then subjected to a Mitsunobu reaction and deprotection to give the corresponding

  从喹啉衍生的具有反式和顺式环己烷主链的手性 P,N-配体可以通过四步从喹啉 N-氧化物轻松合成。反式和顺式-2-(喹啉-2-基)环己醇与二苯甲酰酒石酸的混合物经手性拆分，经光延反应脱保护得到相应的顺式异构体，得到对映体纯反式异构体。光学纯的反式和顺式异构体与氯二苯膦或 PAr2NEt2 反应得到反式和顺式 P,N-配体，它们分别用于不对称烯丙基烷基化，ee 和 ee 分别高达 78% 和 84%。
• 1H NMR Determination of Absolute Configuration of 1- or 2-Aryl-Substituted Alcohols and Amines by Means of Their Diastereomers: Novel Separation Technique of Diastereomeric Derivatives of Pyridyl Alcohols by Extraction
  作者：Masato Matsugi、Kinuyo Itoh、Masatomo Nojima、Yuri Hagimoto、Yasuyuki Kita

  DOI：10.1002/1521-3765(20021216)8:24<5551::aid-chem5551>3.0.co;2-v

  日期：2002.12.16

  A convenient method to determine the absolute configuration of trans-2-aryl cyclohexanols, 1-aryl alcohols and amines was achieved. This method takes advantage of the 1H NMR spectroscopic observations of the remarkable high-field shift of C18-CH3 protons caused by the aromatic shielding effect. It is based on a discrimination of the difference of the environments in two diastereomers derived from 3

  实现了确定反式-2-芳基环己醇，1-芳基醇和胺的绝对构型的简便方法。该方法利用了1H NMR光谱观察到的由芳族屏蔽效应引起的C18-CH3质子显着的高场位移。它基于对衍生自3β-乙酰氧基-5-乙烯酸的两种非对映异构体中环境差异的区分。此外，观察到，基于其碱性的差异，通过萃取简单地分离了吡啶醇的相应的非对映异构衍生物。
• Effective Nonenzymatic Kinetic Resolution of (±)-<i>trans</i>-2-Arylcyclohexanols Using 3β-Acetoxyetienic Acid, DCC, and DMAP
  作者：Masato Matsugi、Yuri Hagimoto、Masatomo Nojima、Yasuyuki Kita

  DOI：10.1021/op0200928

  日期：2003.7.1

  (1R,2S)-trans-2-Arylcyclohexanols of high enantiomerically purity were obtained by the simple stirring of the corresponding (+/-)-arylcyclohexanols with 3beta-acetoxyetienic acid, DCC, and DMAP at room temperature.

  通过将相应的(±)-芳基环己醇与3β-乙酰氧基酯酸、DCC（二环己基碳二亚胺）和DMAP（N,N-二甲基氨基吡啶）在室温下简单搅拌，成功获得了高对映体纯度的(1R,2S)-反式-2-芳基环己醇。
• Arnoldi, Claudio; Citterio, Attilio; Minisci, Francesco, Journal of the Chemical Society. Perkin transactions II, 1983, p. 531 - 542
  作者：Arnoldi, Claudio、Citterio, Attilio、Minisci, Francesco

  DOI：——

  日期：——
• Improved Synthesis of Cyclohexane-Backbone Iridium-Complexes of Quinoline-Phosphine and Their Applications in Asymmetric Hydrogenation
  作者：Qibin Liu

  DOI：10.3987/com-20-14284

  日期：——

  The iridium-complexes 3 and 4 with cyclohexane-backbone derived from quinoline were easily synthesized. The key step is cis/trans stereoselective reduction of 2-(quinolin-2-yl)cyclohexanone 5 to trans-2-(quinolin-2-yl)cyclohexanol 6 using Al(Oi-Pr)(3)/i-PrOH and the following diastereomeric optical resolution of racemic 6 using 0.50 equiv (S)-mandelic acid in EtOAc. These complexes were used in the asymmetric hydrogenation of (E)-1,2-diphenylpropene with up to 13% ee/48% cony. using 3 and 35% ee/9% cony. using 4. For the hydrogenation of (2H-chromen-3-yl)methanol, up to 80% ee/95% yield and 72% ee/96% yield were achieved. The same configuration of the products by using 3 and 4 suggested that the absolute configuration was controlled by the configuration of the stereogenic quinolinyl-bearing carbon of the complexes.