[(2S)-3-hydroxy-2-quinolin-4-ylpropyl] acetate | 213478-42-3

• 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: [(2S)-3-hydroxy-2-quinolin-4-ylpropyl] acetate
• CAS: 213478-42-3
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: DLLZJFSAHPRQBO-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(2S)-3-hydroxy-2-quinolin-4-ylpropyl] acetate 在 咪唑 、 氢氧化钾 、 四丁基碘化铵 作用下， 以 吡啶 、 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-4-[(tert-butyldimethylsilyl)oxy]-3-(quinolin-4-yl)butanenitrile
  参考文献：
  名称：

  Asymmetric synthesis of a new simplified dynemicin analogue equipped with a handle

  摘要：

  The new simplified dynemicin analogue 16 was prepared enantio- and diastereoselectively in 17 steps starting from monoacetate (S) 7. It is equipped with a side arm containing a protected primary alcoholic function ('handle'), which can be used for conjugation with DNA-complexing agents or for devising new types of trigger. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.029
• 作为产物：
  描述：

  4-甲基喹啉 在 Aspergillus niger lipase 、 4 A molecular sieve 作用下， 以 水 为溶剂， 反应 45.5h， 生成 [(2S)-3-hydroxy-2-quinolin-4-ylpropyl] acetate
  参考文献：
  名称：

  Lipase catalyzed asymmetrization of quinolyl substituted 1,3-propanediols

  摘要：

  2-(2-Quinolyl)- and 2-(4-quinolyl)-1,3-propanediols 3 and 4 were prepared and asymmetrized by enantioselective acetylation in organic solvent catalyzed by lipases. While monoacetate 5 was best obtained using Celite-supported pig pancreatic lipase (PPL) (97.3% e.e.) as the (R)-enantiomer, both enantiomers of 6 have been obtained using different enzymes: (R)-6 using lipase f'rom Aspergillus niger (84.0% e.e.) and (S)-6 using lipase from Candida antarctica (97.5% e.e.). The absolute: configuration of both monoacetates 5 and 6 has been determined by anomalous X-ray dispersion methodology on the corresponding p-bromobenzoates 11 and 12. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00247-x

文献信息

• Enzymatically Asymmetrised Chiral Building Blocks for the Synthesis of Complex Natural Product Analogues: The Synthesis of Dynemicin Analogues from 2-(Quinolin-4-yl)propane-1,3-diol
  作者：Renata Riva、Luca Banfi、Andrea Basso、Valentina Gandolfo、Giuseppe Guanti

  DOI：10.1002/ejoc.200901478

  日期：2010.5

  Full details of our synthetic approaches directed towards the enantioselective synthesis of new dynemicin analogues each containing a side-arm (a “handle”) incorporating a protected alcohol are reported.

  报告了我们的合成方法的全部细节，这些方法针对新动力霉素类似物的对映选择性合成，每个类似物都包含一个侧臂（“手柄”），并结合了受保护的醇。
• O-Protecting groups as long-range stereocontrolling elements in the addition of acetylides to 4-substituted quinolines
  作者：Giuseppe Guanti、Sara Perrozzi、Renata Riva

  DOI：10.1016/s0957-4166(02)00711-5

  日期：2002.12

  Addition of magnesium acetylides in the presence of chloroformate esters to racemic differently O-protected 2-(4-quinolyl)propanols and to enantiopure 2-(4-quinolyl)-1,3-dialkoxypropanes, prepared by a chemoenzymatic route, gives almost exclusive regioselective attack at C-2, with stereoselectivities from moderate to good, depending mainly on the bulkiness of the O-protecting group present. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Asymmetric synthesis of a new simplified dynemicin analogue equipped with a handle
  作者：Luca Banfi、Andrea Basso、Valentina Gandolfo、Giuseppe Guanti、Renata Riva

  DOI：10.1016/j.tetlet.2004.04.029

  日期：2004.5

  The new simplified dynemicin analogue 16 was prepared enantio- and diastereoselectively in 17 steps starting from monoacetate (S) 7. It is equipped with a side arm containing a protected primary alcoholic function ('handle'), which can be used for conjugation with DNA-complexing agents or for devising new types of trigger. (C) 2004 Elsevier Ltd. All rights reserved.
• Lipase catalyzed asymmetrization of quinolyl substituted 1,3-propanediols
  作者：Luca Banfi、Giuseppe Guanti、Angelo Mugnoli、Renata Riva

  DOI：10.1016/s0957-4166(98)00247-x

  日期：1998.7

  2-(2-Quinolyl)- and 2-(4-quinolyl)-1,3-propanediols 3 and 4 were prepared and asymmetrized by enantioselective acetylation in organic solvent catalyzed by lipases. While monoacetate 5 was best obtained using Celite-supported pig pancreatic lipase (PPL) (97.3% e.e.) as the (R)-enantiomer, both enantiomers of 6 have been obtained using different enzymes: (R)-6 using lipase f'rom Aspergillus niger (84.0% e.e.) and (S)-6 using lipase from Candida antarctica (97.5% e.e.). The absolute: configuration of both monoacetates 5 and 6 has been determined by anomalous X-ray dispersion methodology on the corresponding p-bromobenzoates 11 and 12. (C) 1998 Elsevier Science Ltd. All rights reserved.