(5-phenylpentyl)phosphonous dichloride | 484689-19-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5-phenylpentyl)phosphonous dichloride
• 英文别名: dichloro(5-phenylpentyl)phosphane
• CAS: 484689-19-2
• 化学式: C₁₁H₁₅Cl₂P
• 分子量: 249.12
• InChiKey: HPWIYYMAQYYBRE-UHFFFAOYSA-N

物化性质

• 沸点：
  330.5±21.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  14.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  (5-phenylpentyl)phosphonous dichloride 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-N⁴-isobutyrylcytidine 3'-[N,N-diisopropyl-P-(5-phenylpentyl)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：

  (5-溴正戊基)苯 在 magnesium 、 cadmium(II) chloride 、 三氯化磷 作用下， 以 乙醚 为溶剂， 反应 8.5h， 以39%的产率得到(5-phenylpentyl)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

文献信息

• PHENYLALKYL BACKBONE MODIFIED OLIGODEOXYNUCLEOTIDES, THEIR SYNTHESIS AND THE INFLUENCE OF THE ALKYL CHAIN LENGTH
  作者：Stefan Amberg、Joachim W. Engels

  DOI：10.1081/ncn-100002535

  日期：2001.3.31

  Phenylalkyl modified phosphoramidites (alkyl chain length n = 1, 2, 3, 5; Fig. 1) were synthesised and incorporated into a DNA hexamer (5'-d(GCCp-GCG); p = place of modification). The obtained diastereomeres were separated by RP-HPLC. After hybridisation with the complementary DNA strand T-m-value and thermodynamic data were measured. The stability of duplexes depends on the linker length and the absolute configuration of the backbone modified oligodeoxynucleotides (Rp, Sp).