[(1R,3S)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin-3-yl]methanol | 1219687-56-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: [(1R,3S)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin-3-yl]methanol
• CAS: 1219687-56-5
• 化学式: C₁₈H₂₁NO₃
• 分子量: 299.37
• InChiKey: SDQWUDWHTCMZTJ-KBXCAEBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 [(1R,3S)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin-3-yl]methanol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.25h， 生成
  参考文献：
  名称：

  Anticancer activity of ruthenium(II) arene complexes bearing 1,2,3,4-tetrahydroisoquinoline amino alcohol ligands

  摘要：

  Ruthenium complexes offer potential reduced toxicity compared to current platinum anticancer drugs. 1,2,3,4-tetrahydrisoquinoline amino alcohol ligands were synthesised, characterised and coordinated to an organometallic Ru(II) centre. These complexes were evaluated for activity against the cancer cell lines MCF-7, A549 and MDA-MB-231 as well as for toxicity in the normal cell line MDBK. They were observed to be moderately active against only the MCF-7 cells with the best IC50 value of 34 mu M for the cis-diastereomeric complex C4. They also displayed excellent selectivity by being relatively inactive against the normal MDBK cell line with SI values ranging from 2.3 to 7.4. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.048
• 作为产物：
  描述：

  trans-1-phenyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以70%的产率得到[(1R,3S)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin-3-yl]methanol
  参考文献：
  名称：

  用于不对称转移氢化反应的 C1-取代四氢异喹啉衍生物的合成与筛选

  摘要：

  四氢异喹啉 (TIQ) 衍生物表现出良好的生物活性。然而，TIQ 化合物在不对称催化中的应用是有限的。本文介绍了一系列用于不对称转移氢化 (ATH) 反应的 TIQ 衍生物。合成了手性 TIQ 氨基醇配体并筛选了芳香酮的 ATH 反应。通过实验和计算研究了 C-1 位置上的顺式和反式苯基取代对配体骨架的影响。结果表明，在室温下用 Ru 复合物获得的 TIQ 支架上的反式取向产生更高的周转率，选择性为 94% ee。顺式异构体导致没有选择性的高周转率。反式异构体在较低温度下产生 99% ee。此外，

  DOI：

  10.1002/ejoc.200901159
• 作为试剂：
  描述：

  对硝基苯乙酮 在 [RhCl2(p-cymene)]2 、 [(1R,3S)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinolin-3-yl]methanol 、 potassium tert-butylate 、 异丙醇 作用下， 反应 1.0h， 生成 (S)-1-[4-nitrophenyl]ethanol 、 (1R)-1-(4-nitrophenyl)ethanol
  参考文献：
  名称：

  用于不对称转移氢化反应的 C1-取代四氢异喹啉衍生物的合成与筛选

  摘要：

  四氢异喹啉 (TIQ) 衍生物表现出良好的生物活性。然而，TIQ 化合物在不对称催化中的应用是有限的。本文介绍了一系列用于不对称转移氢化 (ATH) 反应的 TIQ 衍生物。合成了手性 TIQ 氨基醇配体并筛选了芳香酮的 ATH 反应。通过实验和计算研究了 C-1 位置上的顺式和反式苯基取代对配体骨架的影响。结果表明，在室温下用 Ru 复合物获得的 TIQ 支架上的反式取向产生更高的周转率，选择性为 94% ee。顺式异构体导致没有选择性的高周转率。反式异构体在较低温度下产生 99% ee。此外，

  DOI：

  10.1002/ejoc.200901159

文献信息

• An organogel formed from a cyclic β-aminoalcohol
  作者：Chuanqing Kang、Zheng Bian、Yabing He、Fushe Han、Xuepeng Qiu、Lianxun Gao

  DOI：10.1039/c1cc13179f

  日期：——

  A new organogelator with unique structural feature of a cyclic β-aminoalcohol is presented as the first example of gelation by aminoalcohol through hydrogen-bonding between hydroxy and amine.

  作为氨基甲醇通过羟基和胺之间的氢键作用凝胶化的第一个实例，介绍了一种具有独特结构特征的新型环δ-氨基甲醇有机凝胶剂。
• Synthesis of tetrahydroisoquinoline-diamine ligands and their application in asymmetric transfer hydrogenation
  作者：Byron K. Peters、Sai Kumar Chakka、Tricia Naicker、Glenn E.M. Maguire、Hendrik G. Kruger、Pher G. Andersson、Thavendran Govender

  DOI：10.1016/j.tetasy.2010.04.017

  日期：2010.4

  The use of the tetrahydroisoquinoline scaffold is well documented in biologically active compounds. However, reports of the utilisation of tetrahydroisoquinoline compounds in asymmetric catalysis are limited. The synthesis of novel diamine ligands possessing the tetrahydroisoquinoline (tetrahydroisoquinoline) backbone and evaluation of their activity in the asymmetric transfer hydrogenation of acetophenone are presented. The diamine ligands in conjunction with i-PrOH as the hydrogen source and [RhCl2(Cp*)](2) as the metal precursor proved to be the most effective of the tetrahydroisoquinoline derivatives for this catalytic system. Water was found to have a profound influence on the enantioselectivity of the reaction. Optimisation of the amount water, i-PrOH and catalytic loading content rendered the best result of 70% enantioselectivity for the (S)-1-phenylethanol isomer product. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis and Screening of C¹-Substituted Tetrahydroisoquinoline Derivatives for Asymmetric Transfer Hydrogenation Reactions
  作者：Sai Kumar Chakka、Pher G. Andersson、Glenn E. M. Maguire、Hendrik G. Kruger、Thavendran Govender

  DOI：10.1002/ejoc.200901159

  日期：2010.2

  Tetrahydroisoquinoline (TIQ) derivatives exhibit good biological activity. However, utilization of TIQ compounds in asymmetric catalysis is limited. This paper presents a series of TIQ derivatives in asymmetric transfer hydrogenation (ATH) reactions. Chiral TIQ amino alcohol ligands were synthesized and screened for the ATH reaction of aromatic ketones. The effect of a cis- and trans-phenyl substitution

  四氢异喹啉 (TIQ) 衍生物表现出良好的生物活性。然而，TIQ 化合物在不对称催化中的应用是有限的。本文介绍了一系列用于不对称转移氢化 (ATH) 反应的 TIQ 衍生物。合成了手性 TIQ 氨基醇配体并筛选了芳香酮的 ATH 反应。通过实验和计算研究了 C-1 位置上的顺式和反式苯基取代对配体骨架的影响。结果表明，在室温下用 Ru 复合物获得的 TIQ 支架上的反式取向产生更高的周转率，选择性为 94% ee。顺式异构体导致没有选择性的高周转率。反式异构体在较低温度下产生 99% ee。此外，
• Anticancer activity of ruthenium(II) arene complexes bearing 1,2,3,4-tetrahydroisoquinoline amino alcohol ligands
  作者：Madichaba P. Chelopo、Sachin A. Pawar、Mxolisi K. Sokhela、Thavendran Govender、Hendrik G. Kruger、Glenn E.M. Maguire

  DOI：10.1016/j.ejmech.2013.05.048

  日期：2013.8

  Ruthenium complexes offer potential reduced toxicity compared to current platinum anticancer drugs. 1,2,3,4-tetrahydrisoquinoline amino alcohol ligands were synthesised, characterised and coordinated to an organometallic Ru(II) centre. These complexes were evaluated for activity against the cancer cell lines MCF-7, A549 and MDA-MB-231 as well as for toxicity in the normal cell line MDBK. They were observed to be moderately active against only the MCF-7 cells with the best IC50 value of 34 mu M for the cis-diastereomeric complex C4. They also displayed excellent selectivity by being relatively inactive against the normal MDBK cell line with SI values ranging from 2.3 to 7.4. (C) 2013 Elsevier Masson SAS. All rights reserved.