[3-(anthracen-9-yl)propyl]phosphonous dichloride | 484689-22-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: [3-(anthracen-9-yl)propyl]phosphonous dichloride
• 英文别名: 3-anthracen-9-ylpropyl(dichloro)phosphane
• CAS: 484689-22-7
• 化学式: C₁₇H₁₅Cl₂P
• 分子量: 321.186
• InChiKey: YGLJOKLNFXQOQF-UHFFFAOYSA-N

物化性质

• 沸点：
  477.4±24.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.72
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  [3-(anthracen-9-yl)propyl]phosphonous dichloride 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N⁴-isobutyrylcytidine 3'-{N,N-diisopropyl-P-[3-(anthracen-9-yl)propyl]phosphonamidite}
  参考文献：
  名称：

  Synthesis and Properties of Nonpolar DNA (Arylalkyl)phosphonates

  摘要：

  The eight (arylalkyl)-modified phosphoramidites (=(arylalkyl)phosphonamidites) 1-8 (Fig. 2) were synthesized (Schemes 1-3) and incorporated at different positions into 2'-deoxyoligonucleotides. The [P(R)]and [P(S)]-diastereoisomers of the hexanucleotides 32-39 (Table 1) and of the dodecanucleotides 41-45 (Table 2) obtained were separated by means of reversed-phase HPLC. UV, CD, and fluorescence spectroscopy were used to investigate the thermal stability (T-m) and the structural changes of their DNA duplexes with 5'-d(CGCGCG)-3' and 5'-d(ATGATTGACCTG)-3', respectively. The T-m values significantly depend on the place of modification (Table 2). A dangling-end effect is observed when the [3-(anthracen-9-yl)propyl]-modified 8 is attached at the 5'-terminus (see duplex with 45c). In the case of the incorporation of aromatic moieties tethered via a methylene linker to the P-atom (benzyl- and (naphthalen-1-ylmethyl)-modified 1 and 6, resp.), the duplexes with the [P(R)]-oligonucleotides are more stable than those with the [P(S)]-isomers, whereas in the case of longer alkyl chains at the P-atom (see 2-5), the T-m values show the reverse tendency. The observed T-m differences are assigned to changes in base stacking (Figs. 6 and 7).

  DOI：

  10.1002/1522-2675(200208)85:8<2503::aid-hlca2503>3.0.co;2-i
• 作为产物：
  描述：

  ω-(anthracene-9-yl)propanol 在 四溴化碳 、 三辛基膦 、 magnesium 作用下， 以 乙醚 为溶剂， 反应 36.5h， 生成 [3-(anthracen-9-yl)propyl]phosphonous dichloride
  参考文献：
  名称：

  Synthesis and Properties of Nonpolar DNA (Arylalkyl)phosphonates

  摘要：

  The eight (arylalkyl)-modified phosphoramidites (=(arylalkyl)phosphonamidites) 1-8 (Fig. 2) were synthesized (Schemes 1-3) and incorporated at different positions into 2'-deoxyoligonucleotides. The [P(R)]and [P(S)]-diastereoisomers of the hexanucleotides 32-39 (Table 1) and of the dodecanucleotides 41-45 (Table 2) obtained were separated by means of reversed-phase HPLC. UV, CD, and fluorescence spectroscopy were used to investigate the thermal stability (T-m) and the structural changes of their DNA duplexes with 5'-d(CGCGCG)-3' and 5'-d(ATGATTGACCTG)-3', respectively. The T-m values significantly depend on the place of modification (Table 2). A dangling-end effect is observed when the [3-(anthracen-9-yl)propyl]-modified 8 is attached at the 5'-terminus (see duplex with 45c). In the case of the incorporation of aromatic moieties tethered via a methylene linker to the P-atom (benzyl- and (naphthalen-1-ylmethyl)-modified 1 and 6, resp.), the duplexes with the [P(R)]-oligonucleotides are more stable than those with the [P(S)]-isomers, whereas in the case of longer alkyl chains at the P-atom (see 2-5), the T-m values show the reverse tendency. The observed T-m differences are assigned to changes in base stacking (Figs. 6 and 7).

  DOI：

  10.1002/1522-2675(200208)85:8<2503::aid-hlca2503>3.0.co;2-i