diethyl (1,1-diethoxyethyl)phosphonate | 17056-15-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl (1,1-diethoxyethyl)phosphonate
• 英文别名: (1,1-diethoxy-ethyl)-phosphonic acid diethyl ester；1-(1,1-Diethoxyethyl-ethoxyphosphoryl)oxyethane；1-diethoxyphosphoryl-1,1-diethoxyethane
• CAS: 17056-15-4
• 化学式: C₁₀H₂₃O₅P
• 分子量: 254.263
• InChiKey: YBJBSDKZYJCMTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (1,1-diethoxyethyl)phosphonate 在 正丁基锂 、 偶氮二甲酸二异丙酯 、 三氟化硼乙醚 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成
  参考文献：
  名称：

  摘要：

  Chimeric DNA molecules containing four different linking groups, the natural phosphate, 5'-methylenephosphonate. bis(methylene)phosphinate, and bis(methylene) sulfone (see Fig.1), were directly compared for their ability to form duplexes with complementary DNA and DNA chimeras. From melting temperatures for analogous complementary sequences, general conclusions about the impact of geometric distortion of the internucleotide linkage around the two P-O-C bridges were drawn, as were conclusions about the impact on duplex stability that arises from the removal of the negative charge in the linking group. Each structural perturbation diminished the melting temperature, by ca. -2.5degrees per modification for the 5'-methylenephosphonate, -3.5degrees per modification for the bis(methylene)phosphinate, and -4.5degrees per modification for the bis(methylene) sulfone linker. These results have implications for DNA chemistry including the design of 'antisense' candidates and the proposal of alternative genetic materials in the search for non-terrean life.

  DOI：

  10.1002/1522-2675(200209)85:9<2777::aid-hlca2777>3.0.co;2-1
• 作为产物：
  描述：

  1,1-二乙氧基乙烯 、 亚磷酸二乙酯 生成 diethyl (1,1-diethoxyethyl)phosphonate
  参考文献：
  名称：

  KeteneO,N-,S,N-和N,N-乙缩醛与亚磷酸二乙酯制备烯胺膦酸酯的新方法

  摘要：

  1-二甲氨基-1-甲氧基-1-烯烃（乙烯酮O,N-缩醛）、1-二甲氨基-1-乙硫基-1-烯烃（乙烯酮S,N-缩醛）和1,1-双（二甲氨基）乙烯（乙烯酮 N,N-乙缩醛）与亚磷酸二乙酯反应，得到相应的 (E)-二乙基 1-二甲氨基-1-烯基膦酸酯。尽管乙烯酮二乙基缩醛（乙烯酮 O,O-乙缩醛）与亚磷酸二乙酯反应得到 1,1-二乙氧基-1-乙基膦酸二乙酯，但 1,1-双（乙硫基）-1-烯烃（乙烯酮 S,S-缩醛）没有与亚磷酸二乙酯反应。

  DOI：

  10.1246/bcsj.48.2103

文献信息

• Moskva,V.V. et al., Journal of general chemistry of the USSR, 1967, vol. 37, p. 1540 - 1543
  作者：Moskva,V.V. et al.

  DOI：——

  日期：——
• Moskva,V.V. et al., Journal of general chemistry of the USSR, 1969, vol. 39, p. 2391 - 2393
  作者：Moskva,V.V. et al.

  DOI：——

  日期：——
• Synthesis of the Nanomolar Photoaffinity GABAB Receptor Ligand CGP 71872 Reveals Diversity in the Tissue Distribution of GABAB Receptor Forms
  作者：Michel Belley、Richard Sullivan、Austin Reeves、Jilly Evans、Gary O'Neill、Gordon Y.K. Ng

  DOI：10.1016/s0968-0896(99)00214-x

  日期：1999.12

  A radioiodinated probe, [I-125]-CGP 71872, containing an azido group that can be photoactivated, was synthesized and used to characterize GABA(B) receptors. Photoaffinity labeling experiments using crude membranes prepared from rat brain revealed two predominant ligand binding species at similar to 130 and similar to 100 kDa believed to represent the long (GABA(B)R1a) and short (GABA(B)R1b) forms of the receptor. Indeed, these ligand binding proteins were immunoprecipitated using a GABA(B) receptor-specific antibody confirming the receptor specificity of the photoaffinity probe. Most convincingly, [I-125]-CGP 71872 binding was competitively inhibited in a dose-dependent manner by cold CGP 71872, GABA, saclofen, (-)-baclofen, (+)-baclofen and (L)-glutamic acid with a rank order and stereospecificity characteristic of the GABA(B) receptor. Photoaffinity labeling experiments revealed that the recombinant GABA(B)R2 receptor does not bind; [I-125]-CGP 71872, providing surprising and direct evidence that CGP 71872 is a GABA(B)R1 selective antagonist. Photoaffinity labeling experiments using rat tissues showed that both GABA(B)R1a and GABA(B)R1b are co-expressed in the brain, spinal cord, stomach and testis, but only the short GABA(B)R1b receptor form was detected in kidney and liver whereas the long GABA(B)R1a form was selectively expressed in the adrenal gland, pituitary, spleen and prostate. We report herein the synthesis and biochemical characterization of the nanomolar affinity [I-125]-CGP 71872 and CGP 71872 GABA(B)R1 ligands, and differential tissue expression of the long GABA(B)R1a and short GABA(B)R1b receptor forms in rat and dog. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Moskva,V.V. et al., Journal of general chemistry of the USSR, 1968, vol. 38, p. 202
  作者：Moskva,V.V. et al.

  DOI：——

  日期：——
• Synthesis of Dialkyl 1-Alkoxyvinylphosphonates
  作者：P. GOLBORN

  DOI：10.1055/s-1973-22261

  日期：——