(4-phenylbutyl)phosphonous dichloride | 484689-18-1

• 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: (4-phenylbutyl)phosphonous dichloride
• 英文别名: Dichloro(4-phenylbutyl)phosphane
• CAS: 484689-18-1
• 化学式: C₁₀H₁₃Cl₂P
• 分子量: 235.093
• InChiKey: COOITNYPKNBEIE-UHFFFAOYSA-N

物化性质

• 沸点：
  315.0±21.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (4-phenylbutyl)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-(4-phenylbutyl)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：

  4-苯基-1-丁基溴 在 magnesium 、 cadmium(II) chloride 、 三氯化磷 作用下， 以 乙醚 为溶剂， 反应 7.5h， 以64%的产率得到(4-phenylbutyl)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

• Process for preparing phosphonyloxyacyl amino acids and derivates thereof
  申请人：E.R. Squibb & Sons, Inc.

  公开号：EP0237264A2

  公开（公告）日：1987-09-16

  A process is provided for preparing phosphonyloxyacylamino acids and derivatives thereof having the structure wherein which includes the steps of treating a phosphonic acid dichloride of the structure with an a-hydroxy acid of the structure in the presence of base such as triethylamine at reduced temperatures to form the cyclic mixed anhydride of the structure (which is a new intermediate) and reacting the cyclic mixed anhydride with an amino acid or ester of the structure HX in the presence of base such as triethylamine produces the ACE inhibitor compound In an alternative process, the cyclic anhydride is quenched with water to form the diacid which is treated with a condensing agent such as dicyclohexyl carbodiimide (DCC), 1,1-carbonytdiimidazole (CDI) or thionyl chloride followed by quenching with the amino acid HX produces the above ACE inhibitor compound. In another variation of the process of the invention, the above cyclic anhydride is treated with an alcohol of the structure R30H to form the phosphonic acid diester which may be coupled with the amino acid or ester HX to form the ACE inhibitor

  提供了一种制备磷酰氧基乙酰胺及其衍生物的工艺，其结构如下 其中 其中包括以下步骤 将结构如下的膦酸二氯化物与结构如下的 a-羟基酸一起处理 结构的 a-羟基酸 在碱如三乙胺存在下，在降低的温度下形成结构式的环状混合酸酐 (这是一种新的中间体），然后将环状混合酸酐与结构式的氨基酸或酯反应 HX 在三乙胺等碱存在下反应生成 ACE 抑制剂化合物 在另一种工艺中，环状酸酐用水淬灭后形成二酸 再用缩合剂如二环己基碳二亚胺（DCC）、1,1-碳二咪唑（CDI）或亚硫酰氯处理，然后用氨基酸淬灭 HX 产生上述 ACE 抑制剂化合物。 在本发明工艺的另一种变化中，上述环状酸酐用结构如下的醇处理 R30H 形成膦酸二酯 可与氨基酸或酯类偶联 HX 形成 ACE 抑制剂
• US4885380A
  申请人：——

  公开号：US4885380A

  公开（公告）日：1989-12-05
• US4900860A
  申请人：——

  公开号：US4900860A

  公开（公告）日：1990-02-13
• Synthesis and Properties of Nonpolar DNA (Arylalkyl)phosphonates
  作者：Stefan Amberg、Joachim W. Engels

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

  日期：2002.8

  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).