(1R,3S)-2-(benzyloxycarbonyl)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid | 1240163-16-9

• 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)-2-(benzyloxycarbonyl)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
• CAS: 1240163-16-9
• 化学式: C₂₆H₂₅NO₆
• 分子量: 447.488
• InChiKey: ZUIRHIUKQJGIRC-XUZZJYLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  85.3
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1R,3S)-2-(benzyloxycarbonyl)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 在 吡啶 、 二碳酸二叔丁酯 、 碳酸氢铵 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以75%的产率得到benzyl (1R,3S)-3-carbamoyl-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate
  参考文献：
  名称：

  Pawar, Sunayna S.; Chakka, Sai Kumar; Andersson, Pher G., South African Journal of Chemistry, 2012, vol. 65, p. 23 - 29

  摘要：

  DOI：
• 作为产物：
  描述：

  (1R,3S)-2-benzyl 3-methyl 6,7-dimethoxy-1-phenyl-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylate 在 lithium hydroxide monohydrate 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 72.0h， 以96%的产率得到(1R,3S)-2-(benzyloxycarbonyl)-6,7-dimethoxy-1-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of tetrahydroisoquinoline (TIQ)–oxazoline ligands and their application in enantioselective Henry reactions

  摘要：

  A novel family of eleven new tetrahydroisoquinoline (TIQ)-oxazoline intermediates and five corresponding copper(II) catalysts has been developed and applied to the catalytic asymmetric Henry reaction of various aldehydes with nitromethane to provide beta-hydroxy nitroalkanes in high conversion (>99%) This paper describes the synthesis of the TIQ compounds from L-dihydroxyphenylalanine (L-DOPA) as the starting material The chiral ligands were complexed in situ with various transition metals such as Cu, Sc, Co, Zn, Ni and Mn and tested as a chiral catalyst for the Henry reaction The reaction was optimized in terms of the metal, counter ion, solvent, temperature and over a range of substrates The corresponding catalyst with copper(II) acetate and 2-propanol as the solvent provides the best enantioselectivities (up to 77% ee) of the corresponding nitroalcohol for 4-chlorobenzaldehyde (C) 2010 Elsevier Ltd All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.053

文献信息

• Microwave-Assisted Synthesis of Guanidine Organocatalysts Bearing a Tetrahydroisoquinoline Framework and Their Evaluation in Michael Addition Reactions
  作者：Tricia Naicker、Per I. Arvidsson、Hendrik G. Kruger、Glenn E. M. Maguire、Thavendran Govender

  DOI：10.1002/ejoc.201200303

  日期：2012.6

  simple and practical syntheses of chiral guanidine organocatalysts and their evaluation in the asymmetric Michael addition reaction of malonates and beta-keto esters with nitro-olefins is reported. These organocatalysts are the first of their kind based on a tetrahydroisoquinoline framework. In addition, a microwave-assisted procedure for introducing the guanidine unit onto amino amide derivatives is reported

  报道了手性胍有机催化剂的简单实用合成及其在丙二酸酯和β-酮酯与硝基烯烃的不对称迈克尔加成反应中的评价。这些有机催化剂是同类中第一个基于四氢异喹啉骨架的催化剂。此外，还报道了将胍单元引入氨基酰胺衍生物的微波辅助程序。获得的手性产物具有定量化学效率（高达 99% 的产率）和出色的对映选择性（高达 97% ee）。
• 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.