4-羟基-3-氧代丁基-1-膦酸 | 51827-90-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-羟基-3-氧代丁基-1-膦酸
• 中文别名: (R)-3-氨基-4-(2,4,5-三氟苯基)丁酸
• 英文名称: 4-hydroxy-3-oxobutylphosphonic acid
• 英文别名: 4-Hydroxy-3-oxobutyl-1-phosphonic acid；(4-hydroxy-3-oxobutyl)phosphonic acid
• CAS: 51827-90-8
• 化学式: C₄H₉O₅P
• 分子量: 168.086
• InChiKey: OWWMLFPVVKPREV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  L(-)-甘油醛 、 4-羟基-3-氧代丁基-1-膦酸 在 sodium hydroxide 、 fructose 1,6-bisphosphate aldolase 作用下， 反应 48.0h， 以87%的产率得到2-deoxy-L-arabino-hept-3-ulose 1-phosphonate disodium salt
  参考文献：
  名称：

  实用合成的4-羟基-3-氧代丁基膦酸及其作为DHAP醛缩酶的生物立体异构底物的评价

  摘要：

  基于廉价的4-乙氧基-1-羟基丁烷-2-酮，使用Arbusow反应（总收率59％）开发出了一种有效的四步合成标题化合物4-羟基-3-氧代丁基膦酸酯（2）的方法。测试了几种具有不同立体特异性的二羟基丙酮依赖性醛缩酶对这种膦酰基甲基底物模拟物作为醛醇供体的接受性。发现属于I型（席夫碱形成）和II型（Zn2 +催化）机理类别的单个酶催化2向简单醛的立体选择性加成，从而以高收率提供糖1磷酸酯的生物立体异构体。关于最新的蛋白质X射线数据，讨论了特定酶缺乏接受性的问题。

  DOI：

  10.1016/s0008-6215(97)10026-x
• 作为产物：
  描述：

  3-氧代-4-羟基丁基-1-膦酸二乙酯 在 三甲基溴硅烷 、 水 作用下， 以91%的产率得到4-羟基-3-氧代丁基-1-膦酸
  参考文献：
  名称：

  An improved synthesis of phosphonomethyl analogues of glyceraldehyde- 3-phosphate and dihydroxy-acetone phosphate

  摘要：

  Compounds 1 and 2, phosphonate analogues of dihydroxy-acetone phosphate (DHAP) and glyceraldehyde-3-phosphate (GAP) respectively, are easily and quantitatively obtained from diethyl-4,4-diethoxy-3-hydroxybutyl-1-phosphonate 3. Depending upon the acidic conditions utilised for the deprotection of the phosphonate and carbonyl groups, the aldol/ketol rearrangement allows the synthesis of either compound.

  DOI：

  10.1016/0040-4039(95)01678-b

文献信息

• Monofluorophosphonates as phosphate mimics in bioorganic chemistry: a comparative study of CH2-, CHF- and CF2-phosphonate analogues of sn-glycerol-3-phosphate as substrates for sn-glycerol-3-phosphate dehydrogenase
  作者：Jens Nieschalk、David O'Hagan

  DOI：10.1039/c39950000719

  日期：——

  The synthesis of the cyclohexylammonium salts of 3-(S),4-dihydroxy-1(R,S)-fluorobutylphosphonic acid 3 and 1,1-difluoro-3-(S),4-dihydroxybutylphosphonic acid 4 is reported; 3 is a better substrate for NADH linked sn-glycerol-3-phosphate dehydrogenase than the difluoromethylenephosphonate 4; a comparative study of the CH2-, CHF and CF2- phosphonate analogues of sn-glycerol-3-phosphate is reported.

  报告了 3-(S),4-二羟基-1(R,S)-氟丁基膦酸 3 和 1,1-二氟-3-(S),4-二羟基丁基膦酸 4 的环己胺盐的合成；与二氟甲基膦酸 4 相比，3 是 NADH 链接的炔甘油-3-磷酸脱氢酶的更好底物；报告了对炔甘油-3-磷酸的 CH2-、CHF 和 CF2-膦酸类似物的比较研究。
• Chemical-enzymatic synthesis of azasugar phosphonic acids as glycosyl phosphate surrogates
  作者：Matthias Schuster、Wei-Fang He、Siegfried Blechert

  DOI：10.1016/s0040-4039(01)00137-x

  日期：2001.3

  Starting from achiral materials two stereoisomeric phosphonylated dihydroxypyrrolidines containing four stereogenic centers were synthesized enantioselectively employing a combination of enzymatic and transition-metal-mediated methods. Both compounds contain features of the transition state of the enzyme-catalyzed fucosyl transfer reaction and represent building blocks of potential inhibitors against this class of enzymes. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Isosteres of natural phosphates. 2. Synthesis of the monosodium salt of 4-hydroxy-3-oxobutyl-l-phosphonic acid an isostere of dihydroxyacetone phosphate
  作者：Stephen L. Goldstein、Diza Braksmayer、Burton E. Tropp、Robert Engel

  DOI：10.1021/jm00249a026

  日期：1974.3
• Practical synthesis of 4-hydroxy-3-oxobutylphosphonic acid and its evaluation as a bio-isosteric substrate of DHAP aldolase
  作者：Hans-Lothar Arth、Wolf-Dieter Fessner

  DOI：10.1016/s0008-6215(97)10026-x

  日期：1997.12

  inexpensive 4-ethoxy-1-hydroxybutane-2-one using an Arbusow reaction (59% overall yield). Several dihydroxyacetone-dependent aldolases having different stereospecificities were tested for their acceptance of this phosphonomethyl substrate mimic as the aldol donor. Individual enzymes belonging to both type I (Schiff base formation) and type II (Zn2+ catalysis) mechanistic classes were found to catalyze

  基于廉价的4-乙氧基-1-羟基丁烷-2-酮，使用Arbusow反应（总收率59％）开发出了一种有效的四步合成标题化合物4-羟基-3-氧代丁基膦酸酯（2）的方法。测试了几种具有不同立体特异性的二羟基丙酮依赖性醛缩酶对这种膦酰基甲基底物模拟物作为醛醇供体的接受性。发现属于I型（席夫碱形成）和II型（Zn2 +催化）机理类别的单个酶催化2向简单醛的立体选择性加成，从而以高收率提供糖1磷酸酯的生物立体异构体。关于最新的蛋白质X射线数据，讨论了特定酶缺乏接受性的问题。
• An improved synthesis of phosphonomethyl analogues of glyceraldehyde- 3-phosphate and dihydroxy-acetone phosphate
  作者：P. Page、C. Blonski、J. Périé

  DOI：10.1016/0040-4039(95)01678-b

  日期：1995.10

  Compounds 1 and 2, phosphonate analogues of dihydroxy-acetone phosphate (DHAP) and glyceraldehyde-3-phosphate (GAP) respectively, are easily and quantitatively obtained from diethyl-4,4-diethoxy-3-hydroxybutyl-1-phosphonate 3. Depending upon the acidic conditions utilised for the deprotection of the phosphonate and carbonyl groups, the aldol/ketol rearrangement allows the synthesis of either compound.