(1R)-1,2,3,5-tetra-O-benzyl-1-C-(2-phenylquinolin-4-yl)-D-arabinitol | 1206526-23-9

• 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: (1R)-1,2,3,5-tetra-O-benzyl-1-C-(2-phenylquinolin-4-yl)-D-arabinitol
• 英文别名: (2R,3R,4R,5R)-1,3,4,5-tetrakis(phenylmethoxy)-5-(2-phenylquinolin-4-yl)pentan-2-ol
• CAS: 1206526-23-9
• 化学式: C₄₈H₄₅NO₅
• 分子量: 715.889
• InChiKey: BSUQPTDLRGYCCC-MABAWHDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  54
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  70
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R)-1,2,3,5-tetra-O-benzyl-1-C-(2-phenylquinolin-4-yl)-D-arabinitol 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 60.0 ℃ 、275.8 kPa 条件下， 生成
  参考文献：
  名称：

  Povarov reactions of exo-glycals: preparation of C-linked, quinoline analogues

  摘要：

  A one-pot approach based upon the Povarov reaction has been efficiently employed with a number of exo-glycals and para-substituted benzanilines to synthesize novel open-ring, carbohydrate-derived quinolines. The mechanism of this reaction was studied and an explanation for the observed stereo-selectivity is proposed. Treatment of the compounds with the Lewis acid, boron trichloride, successfully removes the benzyl ether protecting groups in good yields. Several of the prepared compounds have been screened in the National Cancer Institute's (NCI's) 60 cell line model. Moderate activity was observed for several leukemia cell lines. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.077
• 作为产物：
  描述：

  N-苄叉苯胺 、 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol 在 scandium tris(trifluoromethanesulfonate) 、 manganese(IV) oxide 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以65%的产率得到(1R)-1,2,3,5-tetra-O-benzyl-1-C-(2-phenylquinolin-4-yl)-D-arabinitol
  参考文献：
  名称：

  Facile one-pot method for the synthesis of novel glycosylidene-based quinolines

  摘要：

  A one-pot approach to the synthesis of novel glycosylidene-based quinolines is described. The reaction involves a Lewis acid catalyzed Povarov addition followed by oxidation of the resulting spiroanellated tetrahydroquinoline intermediates to yield the open-ring glycosylidene-derived quinoline. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.10.129

文献信息

• Povarov reactions of exo-glycals: preparation of C-linked, quinoline analogues
  作者：Peter H. Dobbelaar、Cecilia H. Marzabadi

  DOI：10.1016/j.tet.2011.09.077

  日期：2011.12

  A one-pot approach based upon the Povarov reaction has been efficiently employed with a number of exo-glycals and para-substituted benzanilines to synthesize novel open-ring, carbohydrate-derived quinolines. The mechanism of this reaction was studied and an explanation for the observed stereo-selectivity is proposed. Treatment of the compounds with the Lewis acid, boron trichloride, successfully removes the benzyl ether protecting groups in good yields. Several of the prepared compounds have been screened in the National Cancer Institute's (NCI's) 60 cell line model. Moderate activity was observed for several leukemia cell lines. (C) 2011 Elsevier Ltd. All rights reserved.
• Facile one-pot method for the synthesis of novel glycosylidene-based quinolines
  作者：Peter H. Dobbelaar、Cecilia H. Marzabadi

  DOI：10.1016/j.tetlet.2009.10.129

  日期：2010.1

  A one-pot approach to the synthesis of novel glycosylidene-based quinolines is described. The reaction involves a Lewis acid catalyzed Povarov addition followed by oxidation of the resulting spiroanellated tetrahydroquinoline intermediates to yield the open-ring glycosylidene-derived quinoline. (C) 2009 Elsevier Ltd. All rights reserved.