2-cyanoethoxy(N,N-diethylamino)chlorophosphine | 110914-51-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-cyanoethoxy(N,N-diethylamino)chlorophosphine
• 英文别名: 2-cyanoethyl N,N-diethylchlorophosphoramidite；chloro-β-cyanoethyl-N,N-diisopropylamino-phosphoramidite；2-cyanoethyl N,N-diethylphosphorochloroamidite；N,N-diethyl-2-O-cyanoethyl phosphorochloridite；(2-cyanoethoxy)-(N,N-diethylamino)chlorophosphoramidite；3-[Chloro(diethylamino)phosphanyl]oxypropanenitrile
• CAS: 110914-51-7
• 化学式: C₇H₁₄ClN₂OP
• 分子量: 208.628
• InChiKey: SALAARIOGQHTFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-cyanoethoxy(N,N-diethylamino)chlorophosphine 、 N4-苯甲酰基-5′-O-(4,4′-二甲氧基三苯基)-2′-脱氧胞苷 在 N,N-二异丙基乙胺 作用下， 反应 0.5h， 以91%的产率得到N-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine-3'-O-[O-(2-cyanoethyl)-N,N-diethylphosphoramidite]
  参考文献：
  名称：

  Overcoming hydrolytic sensitivity and low solubility of phosphitylation reagents by combining ionic liquids with mechanochemistry

  摘要：

  离子液体与球磨相结合，用于一系列氯代磷酰胺试剂，对核苷和 2-脱氧核苷进行磷酸化。离子液体介导的过程具有更高的稳定性，加上球磨产生的高效传质，即使使用小的二烷基氨基和更常用的二异丙基氨基保护，也能获得极高的产量。

  DOI：

  10.1039/c1cc11025j
• 作为产物：
  描述：

  二乙胺 、 3-羟基丙腈 在 N,N-二异丙基乙胺 、 三氯化磷 作用下， 反应 1.17h， 生成 2-cyanoethoxy(N,N-diethylamino)chlorophosphine
  参考文献：
  名称：

  Overcoming hydrolytic sensitivity and low solubility of phosphitylation reagents by combining ionic liquids with mechanochemistry

  摘要：

  离子液体与球磨相结合，用于一系列氯代磷酰胺试剂，对核苷和 2-脱氧核苷进行磷酸化。离子液体介导的过程具有更高的稳定性，加上球磨产生的高效传质，即使使用小的二烷基氨基和更常用的二异丙基氨基保护，也能获得极高的产量。

  DOI：

  10.1039/c1cc11025j

文献信息

• Synthesis and characterization of mannosylated oligoribonucleotides
  作者：Yuyan Zhao、Kha Tram、Hongbin Yan

  DOI：10.1016/j.carres.2009.08.033

  日期：2009.11

  Oligoribonucleotide (RNA)-carbohydrate conjugates bearing mono- and divalent mannosides were readily obtained using 3,4-diethoxy-3-cyclobutene-1,2-dione as the linking agent in the presence of trace amount of triethylamine. The glycoconjugates were purified by HPLC and characterized by electrospray mass spectroscopy.

  在痕量三乙胺的存在下，使用3,4-二乙氧基-3-环丁烯-1,2-二酮作为连接剂，可以轻松获得带有一价和二价甘露糖苷的寡核糖核苷酸（RNA）-碳水化合物共轭物。糖缀合物通过HPLC纯化，并通过电喷雾质谱法表征。
• Selective synthesis of chlorophosphoramidites using ionic liquids
  作者：Eric J. Amigues、Christopher Hardacre、Gillian Keane、Marie E. Migaud、Sarah E. Norman、William R. Pitner

  DOI：10.1039/b905000k

  日期：——

  sensitivity and impurity issues hampering existing traditional synthetic routes have been eased. Not only can stock chemicals be used without purification, but the reactions may be conducted at room temperature and at high concentrations. Furthermore, reaction times are reduced and rapid addition of reagents is possible whilst retaining tight control over product selectivity. Beyond their role as reaction

  一系列的氯代亚磷酰胺已经被制备出来。 离子液体 并与分子合成的材料进行比较 溶剂。通过使用离子液体作为反应介质，湿气敏感性和杂质问题困扰了现有的传统合成路线，现已得到缓解。不仅可以不使用库存化学品纯化，但是反应可以在室温和高浓度下进行。此外，减少了反应时间，并且可以在保持对产物选择性的严格控制的同时快速添加试剂。除了它们作为反应介质的作用之外，离子液体 还为这些对水分高度敏感的氯代亚磷酰胺提供了独特的存储介质。
• Synthesis of diphosphorylated and diphosphonylated Lipid A monosaccharide analogues via phosphite intermediates
  作者：P. Westerduin、G. H. Veeneman、J. H. van Boom

  DOI：10.1002/recl.19871061201

  日期：——

  The synthesis of two Lipid A monosaccharide analogues, 3-O-palmitoyl-2-deoxy-2-palmitamido-α-D-glucopyranose 1,4-diphosphate (1) and the corresponding 1,4-bis(1H-phosphonate) (2), is described. The introduction of the phosphate functions was achieved via phosphitylation of the anomeric and non-anomeric hydroxyl groups with the monofunctional phosphitylating reagents benzyl 2-cyanoethyl N,N-diethylphosphoramidite

  两种脂质A单糖类似物3-O-棕榈酰基-2-脱氧-2-棕榈酰胺基-α-D-吡喃葡萄糖1,4-二磷酸酯（1）和相应的1,4-双（1H-膦酸酯）的合成（描述2）。通过用单官能磷酸化试剂苄基2-氰基乙基N，N-二乙基亚磷酰胺基（9）和水杨基磷酰氯（10）对异头和非异头羟基进行磷酸化来实现磷酸官能团的引入。氧化中间亚磷酸三酯并随后除去所有保护基团，得到目标分子1和2。
• New nucleoside phosphoramidites and coupling protocols for solid-phase RNA synthesis
  作者：Matthew H. Lyttle、Peter B. Wright、Nanda D. Sinha、J. D. Bain、A. Richard Chamberlin

  DOI：10.1021/jo00015a010

  日期：1991.7

  The 5'-O-(4,4'-dimethoxytrityl)-2'-O-(trialkylsilyl)ribonucleoside 3'-O-(2-cyanoethyl N,N-diethylphosphoramidites) 3, 5, 7, and 9, modified monomers for RNA synthesis, were prepared from 2-cyanoethyl N,N-diethylchloro-phosphoramidite (1). In conjunction with newly developed coupling protocols for automated solid-phase synthesis, they afforded synthetic oligoribonucleotides up to 74 base units in length. The performance of the new compounds was compared to the analogous 5'-O-(4,4'-dimethoxytrityl)-2'-O-(trialkylsilyl)ribonucleoside 3'-O-(2-cyanoethyl N,N-diisopropylphosphoramidites) 4, 6, 8, and 10. Complete removal of benzoyl groups from N2-benzoylguanosine, which was incorporated into some of the synthetic oligoribonucleotides, was demonstrated. Purification procedures by reverse phase HPLC and PAGE methods are also presented.
• Synthesis of fragments of a streptococcus pneumoniae type-specific capsular polysaccharide
  作者：G.H. Veeneman、L.J.F. Gomes、J.H. van Boom

  DOI：10.1016/s0040-4020(01)89206-1

  日期：1989.1