(R)-5,6,7,8-tetrahydroisoquinolin-5-ol | 1085526-35-7

• 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: (R)-5,6,7,8-tetrahydroisoquinolin-5-ol
• 英文别名: (5R)-5,6,7,8-Tetrahydroisoquinolin-5-ol
• CAS: 1085526-35-7
• 化学式: C₉H₁₁NO
• 分子量: 149.192
• InChiKey: FZUMQCKAVKSWLQ-SECBINFHSA-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

• 作为反应物：
  描述：

  (R)-5,6,7,8-tetrahydroisoquinolin-5-ol 、 碘甲烷 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  吗啡生物碱 ACNO 片段的实用不对称合成

  摘要：

  使用 Ru 催化的不对称转移氢化、Pd 催化的环化和 Pt 催化的氢化作为关键步骤，以优异的总产率和光学纯度实现了吗啡生物碱的 ACNO 骨架的不对称全合成。

  DOI：

  10.1055/s-2008-1078021
• 作为产物：
  描述：

  7,8-二氢-6H-异喹啉-5-酮 在 甲酸 、 (S,S)-N-(对甲苯磺酰)-1,2-二苯乙烷二胺(对异丙基苯)氯化钌(II) 、 三乙胺 作用下， 以100%的产率得到(R)-5,6,7,8-tetrahydroisoquinolin-5-ol
  参考文献：
  名称：

  吗啡生物碱 ACNO 片段的实用不对称合成

  摘要：

  使用 Ru 催化的不对称转移氢化、Pd 催化的环化和 Pt 催化的氢化作为关键步骤，以优异的总产率和光学纯度实现了吗啡生物碱的 ACNO 骨架的不对称全合成。

  DOI：

  10.1055/s-2008-1078021

文献信息

• Amine-Tunable Ruthenium Catalysts for Asymmetric Reduction of Ketones
  作者：Sonia Rodríguez、Bo Qu、Keith R. Fandrick、Frederic Buono、Nizar Haddad、Yibo Xu、Melissa A. Herbage、Xingzhong Zeng、Shengli Ma、Nelu Grinberg、Heewon Lee、Zhengxu S. Han、Nathan K. Yee、Chris H. Senanayake

  DOI：10.1002/adsc.201300727

  日期：2014.2.10

  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
• 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.
• A Practical Asymmetric Synthesis of the ACNO Fragment of Morphine Alkaloids
  作者：Ling-Wei Hsin、Li-Te Chang、Huei-Ling Liou

  DOI：10.1055/s-2008-1078021

  日期：——

  Asymmetric total synthesis of the ACNO skeleton of morphine alkaloids has been achieved in excellent overall yields and optical purities using the Ru-catalyzed asymmetric transfer hydrogenation, Pd-catalyzed cyclization, and Pt-catalyzed hydrogenation as key steps.

  使用 Ru 催化的不对称转移氢化、Pd 催化的环化和 Pt 催化的氢化作为关键步骤，以优异的总产率和光学纯度实现了吗啡生物碱的 ACNO 骨架的不对称全合成。