4-(diethoxyphosphoryl)butanoic acid chloride | 75939-46-7

• 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: 4-(diethoxyphosphoryl)butanoic acid chloride
• 英文别名: 4-Diethoxyphosphorylbutanoyl chloride
• CAS: 75939-46-7
• 化学式: C₈H₁₆ClO₄P
• 分子量: 242.639
• InChiKey: QZTMQDRKTRBMRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(diethoxyphosphoryl)butanoic acid chloride 在 正丁基锂 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.5h， 生成 (4R,5R)-trans-N-[4'-(diethoxyphosphoryl)-2'(R)-azidobutanoyl]hexahydro-benzoxazolidin-2-one
  参考文献：
  名称：

  Enantioselective synthesis of (S)-2-amino-3-phosphonopropionic acid, (S)-AP-3, and (R)-2-amino-4-phosphonobutanoic acid, (R)-AP-4, via diastereoselective azidation of (4R,5R)-trans-N-[(diethoxyphosphoryl)propionyl]- and (4R,5R)-trans-N-[(diethoxyphosphoryl)butanoyl]hexahydrobenzoxazolidin-2-one

  摘要：

  N-Acylation of readily available, enantiopure oxazolidinone (4R,5R)-1b with (diethoxyphosphoryl)propionyl chloride and (diethoxyphosphoryl)butanoyl chloride affords de title substrates (4R,5R)-2 and (4R,5R)-7, respectively, which are azidated with high diastereoselectivity by means of the reaction between their sodium enolates (4R,5R)-2-Na and (4R,5R)-7-Na with trisyl azide. Removal of the chiral auxiliary from azidated products (4R,5R,2'S)-3 and (4R,5R,2'R)-8 followed by hydrogenation and hydrolysis of the resulting carboxylic acids (S)-4 and (R)-9 gave the pharmacologically relevant aminophosphonic acids (S)-AP-3 and (R)-AP-4 in good yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.018
• 作为产物：
  描述：

  4-(二乙基膦)丁酸 在 草酰氯 作用下， 以 乙醚 为溶剂， 生成 4-(diethoxyphosphoryl)butanoic acid chloride
  参考文献：
  名称：

  Selective inhibition of Trypanosoma brucei GAPDH by 1,3-bisphospho-d-glyceric acid (1,3-diPG) analogues

  摘要：

  Various phosphono-phosphates and diphosphonates were synthesized as 1,3-diphosphoglycerate (1,3-diPG) analogues by using a beta -ketophosphonate, an alpha -fluoro,beta -ketophosphonate or a beta -ketophosphoramidate to mimic the unstable carboxyphosphate part of the natural substrate. The inhibitory effect of these analogues on glyceraldehyde-3-phosphate dehydrogenases (GAPDH) from Trypanosoma brucei (Tb) and rabbit muscle were measured with respect to both substrates, glyceraldehyde-3-phosphate (GAP) and 1,3-diPG. Interestingly, all 1,5-diphosphono,2-oxopentanes without substitution at the C-3 position selectively inhibit the Tb GAPDH with respect to 1,3-diPG and are without effect on Rm GAPDH. All 1-phospho,3-oxo,4-phosphonobutanes show themselves to be non-selective inhibitors either with regard to substrates or organisms, but they will be of a great interest as 1,3-diPG stable models for structural studies of co-crystals with GAPDHs. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00295-9

文献信息

• A Visible Light Driven Nickel Carbonylation Catalyst: The Synthesis of Acid Chlorides from Alkyl Halides
  作者：Kristian El Chami、Yi Liu、Mohammed A. Belahouane、Yiyang Ma、Pierre‐Louis Lagueux‐Tremblay、Bruce A. Arndtsen

  DOI：10.1002/anie.202213297

  日期：2023.3

  A visible light driven nickel carbonylation catalyst has been develop. This offers a method for carbonylative coupling reactions with an earth abundant metal at ambient temperature for the conversion of alkyl halides into synthetically versatile acid chlorides. The acid chlorides can then be transformed into an array of challenging ester, thioester and amide products.

  已经开发出可见光驱动的镍羰基化催化剂。这提供了一种在环境温度下与地球上丰富的金属进行羰基化偶联反应的方法，用于将卤代烷转化为合成用途广泛的酰氯。然后可以将酰氯转化为一系列具有挑战性的酯、硫酯和酰胺产品。
• [EN] PHOSPHONATE ANALOGS FOR TREATING METABOLIC DISEASES<br/>[FR] ANALOGUES DE PHOSPHONATES CONVENANT AU TRAITEMENT D'AFFECTIONS DU METABOLISME
  申请人：GILEAD SCIENCES INC

  公开号：WO2004096237A2

  公开（公告）日：2004-11-11

  The invention is related to phosphorus substituted compounds with activity for treating metabolic diseases and/or disorders, e.g., diabetes and hypercholesterolemia, compositions containing such compounds, and therapeutic methods that include the administration of such compounds, as well as to processes and intermediates useful for preparing such compounds.
• Selective inhibition of Trypanosoma brucei GAPDH by 1,3-bisphospho-d-glyceric acid (1,3-diPG) analogues
  作者：Sylvain Ladame、Michel Bardet、Jacques Périé、Michèle Willson

  DOI：10.1016/s0968-0896(00)00295-9

  日期：2001.3

  Various phosphono-phosphates and diphosphonates were synthesized as 1,3-diphosphoglycerate (1,3-diPG) analogues by using a beta -ketophosphonate, an alpha -fluoro,beta -ketophosphonate or a beta -ketophosphoramidate to mimic the unstable carboxyphosphate part of the natural substrate. The inhibitory effect of these analogues on glyceraldehyde-3-phosphate dehydrogenases (GAPDH) from Trypanosoma brucei (Tb) and rabbit muscle were measured with respect to both substrates, glyceraldehyde-3-phosphate (GAP) and 1,3-diPG. Interestingly, all 1,5-diphosphono,2-oxopentanes without substitution at the C-3 position selectively inhibit the Tb GAPDH with respect to 1,3-diPG and are without effect on Rm GAPDH. All 1-phospho,3-oxo,4-phosphonobutanes show themselves to be non-selective inhibitors either with regard to substrates or organisms, but they will be of a great interest as 1,3-diPG stable models for structural studies of co-crystals with GAPDHs. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Enantioselective synthesis of (S)-2-amino-3-phosphonopropionic acid, (S)-AP-3, and (R)-2-amino-4-phosphonobutanoic acid, (R)-AP-4, via diastereoselective azidation of (4R,5R)-trans-N-[(diethoxyphosphoryl)propionyl]- and (4R,5R)-trans-N-[(diethoxyphosphoryl)butanoyl]hexahydrobenzoxazolidin-2-one
  作者：Gloria Reyes-Rangel、Virginia Marañón、C. Gabriela Avila-Ortiz、Cecilia Anaya de Parrodi、Leticia Quintero、Eusebio Juaristi

  DOI：10.1016/j.tet.2006.06.018

  日期：2006.8

  N-Acylation of readily available, enantiopure oxazolidinone (4R,5R)-1b with (diethoxyphosphoryl)propionyl chloride and (diethoxyphosphoryl)butanoyl chloride affords de title substrates (4R,5R)-2 and (4R,5R)-7, respectively, which are azidated with high diastereoselectivity by means of the reaction between their sodium enolates (4R,5R)-2-Na and (4R,5R)-7-Na with trisyl azide. Removal of the chiral auxiliary from azidated products (4R,5R,2'S)-3 and (4R,5R,2'R)-8 followed by hydrogenation and hydrolysis of the resulting carboxylic acids (S)-4 and (R)-9 gave the pharmacologically relevant aminophosphonic acids (S)-AP-3 and (R)-AP-4 in good yield. (c) 2006 Elsevier Ltd. All rights reserved.