(S)-1-O-(pyren-1-ylmethyl)glycerol | 682344-99-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: (S)-1-O-(pyren-1-ylmethyl)glycerol
• 英文别名: (2S)-3-[(Pyren-1-YL)methoxy]propane-1,2-diol；(2S)-3-(pyren-1-ylmethoxy)propane-1,2-diol
• CAS: 682344-99-6
• 化学式: C₂₀H₁₈O₃
• 分子量: 306.361
• InChiKey: WQHGVTJIKDXENN-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-O-(pyren-1-ylmethyl)glycerol 在 二异丙基铵盐四氮唑 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 生成 Diisopropyl-phosphoramidous acid (R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-1-(pyren-1-ylmethoxymethyl)-ethyl ester 2-cyano-ethyl ester
  参考文献：
  名称：

  Intercalating nucleic acids: The inversion of the stereocenter in 1-O-(pyren-1-ylmethyl)glycerol from R to S. Thermal stability towards ssDNA, ssRNA and its own type of oligodeoxynucleotides

  摘要：

  The synthesis and insertions of (S)-1-O-(pyren-1-ylmethyl)glycerol into intercalating nucleic acids is described. Insertions of this S-isomer as a bulge lead to reduced binding affinity towards complementary ssDNA compared to intercalating nucleic acids possessing (R)-1-O-(pyren-1-ylmethyl)glycerol in the same positions. Insertions of both (R) or (S) 1-O-(pyren-1-ylmethyl)glycerols as bulges into two complementary strands decreased the stability of the complex compared to dsDNA possessing the pyrene pseudo-nucleotide in one of the strands. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.124
• 作为产物：
  描述：

  1-芘甲醇 在 氢氧化钾 、 氯化亚砜 作用下， 以 甲苯 为溶剂， 生成 (S)-1-O-(pyren-1-ylmethyl)glycerol
  参考文献：
  名称：

  Intercalating nucleic acids: The inversion of the stereocenter in 1-O-(pyren-1-ylmethyl)glycerol from R to S. Thermal stability towards ssDNA, ssRNA and its own type of oligodeoxynucleotides

  摘要：

  The synthesis and insertions of (S)-1-O-(pyren-1-ylmethyl)glycerol into intercalating nucleic acids is described. Insertions of this S-isomer as a bulge lead to reduced binding affinity towards complementary ssDNA compared to intercalating nucleic acids possessing (R)-1-O-(pyren-1-ylmethyl)glycerol in the same positions. Insertions of both (R) or (S) 1-O-(pyren-1-ylmethyl)glycerols as bulges into two complementary strands decreased the stability of the complex compared to dsDNA possessing the pyrene pseudo-nucleotide in one of the strands. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.124

文献信息

• Intercalating nucleic acids: The inversion of the stereocenter in 1-O-(pyren-1-ylmethyl)glycerol from R to S. Thermal stability towards ssDNA, ssRNA and its own type of oligodeoxynucleotides
  作者：Vyacheslav V Filichev、Khalid M.H Hilmy、Ulf B Christensen、Erik B Pedersen

  DOI：10.1016/j.tetlet.2004.04.124

  日期：2004.6

  The synthesis and insertions of (S)-1-O-(pyren-1-ylmethyl)glycerol into intercalating nucleic acids is described. Insertions of this S-isomer as a bulge lead to reduced binding affinity towards complementary ssDNA compared to intercalating nucleic acids possessing (R)-1-O-(pyren-1-ylmethyl)glycerol in the same positions. Insertions of both (R) or (S) 1-O-(pyren-1-ylmethyl)glycerols as bulges into two complementary strands decreased the stability of the complex compared to dsDNA possessing the pyrene pseudo-nucleotide in one of the strands. (C) 2004 Elsevier Ltd. All rights reserved.