(S)-5,6,7,8-tetrahydroisoquinolin-5-ol | 1372452-42-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (S)-5,6,7,8-tetrahydroisoquinolin-5-ol
• 英文别名: (5S)-5,6,7,8-Tetrahydro-5-isoquinolinol；(5S)-5,6,7,8-tetrahydroisoquinolin-5-ol
• CAS: 1372452-42-0
• 化学式: C₉H₁₁NO
• 分子量: 149.192
• InChiKey: FZUMQCKAVKSWLQ-VIFPVBQESA-N

物化性质

• 沸点：
  299.8±25.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  7,8-二氢-6H-异喹啉-5-酮 在 RuCl₂[(2R,2’R,3S,3’S)-MeO-bisdihydrobenzooxaphosphole][(R,R)-dpen] 、 potassium tert-butylate 、 氢气 作用下， 以 异丙醇 、 叔丁醇 为溶剂， 反应 20.0h， 以94%的产率得到
  参考文献：
  名称：

  胺可调谐的钌催化剂，用于酮的不对称还原

  摘要：

  AbstractA series of efficient ruthenium catalysts has been developed for the asymmetric hydrogenation and transfer hydrogenation of ketones with high reactivities and selectivities. The new chiral bisdihydrobenzooxaphosphole (BIBOP)/diamine‐ruthenium complexes catalyzed the enantioselective hydrogenation of substrates such as aryl and heteroaryl cyclic and alkyl ketones with substrate/catalyst (S/C) ratios of up to 100,000. The opposite sense of enantioselectivity can be obtained by proper selection of a diamine with a given chirality of the phosphine. The usefulness of the new system has been demonstrated in the asymmetric hydrogenation of a complex synthetic intermediate towards cholesteryl ester transfer protein (CETP) inhibitors at S/C 20,000 on large‐scale operation.magnified image

  DOI：

  10.1002/adsc.201300727

文献信息

• [EN] NOVEL RUTHENIUM CATALYSTS AND THEIR USE FOR ASYMMETRIC REDUCTION OF KETONES<br/>[FR] NOUVEAUX CATALYSEURS AU RUTHÉNIUM ET LEUR UTILISATION POUR LA RÉDUCTION ASYMÉTRIQUE DE CÉTONES
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2015002769A1

  公开（公告）日：2015-01-08

  Disclosed are novel ruthenium compounds of formula (Ia) and (Ib): wherein R1 and the moiety L ∩ L are defined herein. Also disclosed is a process for using these novel ruthenium compounds as catalysts for asymmetric hydrogenation and transfer hydrogenation of ketones with high reactivities and excellent selectivities.

  揭示了一种新型钌化合物的结构式(Ia)和(Ib)：其中R1和基团L ∩ L在此定义。还揭示了一种使用这些新型钌化合物作为催化剂进行不对称加氢和酮的转移加氢的方法，具有高反应性和优异选择性。
• NOVEL RUTHENIUM CATALYSTS AND THEIR USE FOR ASYMMETRIC REDUCTION OF KETONES
  申请人：HADDAD Nizar

  公开号：US20150005500A1

  公开（公告）日：2015-01-01

  Disclosed are novel ruthenium compounds of formula (Ia) and (Ib): wherein R 1 and the moiety are defined herein. Also disclosed is a process for using these novel ruthenium compounds as catalysts for asymmetric hydrogenation and transfer hydrogenation of ketones with high reactivities and excellent selectivities.

  本发明揭示了一种新型钌化合物的化学式(Ia)和(Ib)：其中R1和该基团在此定义。还揭示了一种使用这些新型钌化合物作为催化剂进行酮类的不对称氢化和转移氢化的方法，具有高反应性和优异选择性。
• Process for preparing phenyl-, pyridinyl- or pyrimidinyl-substituted imidazoles
  申请人：Eisai R&D Management Co., Ltd.

  公开号：EP2261218A2

  公开（公告）日：2010-12-15

  The present invention relates to a process for preparing a compound of formula (6a): which comprises the step of: subjecting a compound of formula (5a): and a compound of formula (4a): to a coupling reaction,

  本发明涉及一种制备式（6a）化合物的工艺： 其中包括以下步骤 将式（5a）化合物 和式 (4a) 的化合物： 进行偶联反应、
• Preparative access to medicinal chemistry related chiral alcohols using carbonyl reductase technology
  作者：Andrew S. Rowan、Thomas S. Moody、Roger M. Howard、Toby J. Underwood、Iain R. Miskelly、Yanan He、Bo Wang

  DOI：10.1016/j.tetasy.2013.09.015

  日期：2013.11

  Libraries of highly enantioenriched secondary alcohols in both enantiomeric forms were synthesised by enzymatic reduction of their parent ketones using selectAZyme (TM) carbonyl reductase (CRED) technology. Commercially available CREDs were able to reduce a range of substrate classes efficiently and with very high enantioselectivity. Matching substrate classes to small subsets of CREDs enabled the fast development of preparative bioreductions and the rapid generation of 100-1500 mg samples of chiral alcohols in typically >95% ee and the majority in >= 99.0% ee. The conditions for small scale synthesis were then scaled up to 0.5 kg to deliver one of the chiral alcohols, (S)-1-(4-bromophenyl)-2-chloroethanol, in 99.8% ee and 91% isolated yield. (C) 2013 Elsevier Ltd. All rights reserved.
• US9029540B2
  申请人：——

  公开号：US9029540B2

  公开（公告）日：2015-05-12