diethyl (2-hydroxypentyl)phosphonate | 128589-10-6

• 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 (2-hydroxypentyl)phosphonate
• 英文别名: Phosphonic acid, (2-hydroxypentyl)-, diethyl ester；1-diethoxyphosphorylpentan-2-ol
• CAS: 128589-10-6
• 化学式: C₉H₂₁O₄P
• 分子量: 224.237
• InChiKey: DIMAZPVJGJKFMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl (2-hydroxypentyl)phosphonate 在 重铬酸吡啶 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以0.921 g的产率得到diethyl (2-oxo-pentyl)-phosphonate
  参考文献：
  名称：

  Asymmetric synthesis of (3S,4R,7S)-(−)-3-hydroxy-7-methoxy-2,2,4-trimethyl-decanoic acid, a plausible polyketide fragment of halipeptin A

  摘要：

  The first enantioselective synthesis of (3S,4R,7S)-(-)-3-hydroxy-7-methoxy-2,2,4-trimethyl-decanoic acid 4 in 11 steps and 6% overall yield, starting from commercially available methyl 2,2-dimethyl-3-hydroxy propionate 5 is described. The stereochemical flexible synthetic pathway involves a Brown's crotylboration reaction and a Corey-Bakshi-Shibata (CBS) oxazaborolidine-mediated reduction. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00622-0
• 作为产物：
  描述：

  甲基膦酸二乙酯 、 正丁醛 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到diethyl (2-hydroxypentyl)phosphonate
  参考文献：
  名称：

  Preparation and reactivity of β-zinc and copper phosphonates

  摘要：

  DOI：

  10.1016/s0040-4039(00)98798-7

文献信息

• Conformational Analysis of (2-Substituted-alkyl)phosphoryl Compounds. 1. NMR Spectroscopic Studies of Dialkyl (2-Hydroxyalkyl)phosphonates and Their Carboxylic Esters
  作者：Daniel G. Genov、John C. Tebby

  DOI：10.1021/jo950364n

  日期：1996.1.1

  Twelve (2-substituted-alkyl)phosphonates (2, 3) were synthesized and conformational analyses carried out by NMR spectroscopy. The conformational populations in six solvents with different polarities and in the presence of metal ions (Li+, Na+, Zn2+), were studied. Steric effects were studied by variation of the sizes of alkyl groups R(1) and R(2) and intramolecular interactions studied by derivatization of the hydroxy group X. In (2-hydroxyalkyl)phosphonates the most stable conformer ga, in which the phosphoryl group is gauche to the hydroxy group and anti to the alkyl group (R(1)), is favored particularly in less polar solvents such as C6D6 and CDCl3. In polar solvents the population of the less stable conformer ag, in which the phosphoryl group is gauche to the alkyl group (R(1)) and anti to the hydroxy group, is increased. Smaller alkyl groups R(1) (Me, Pr-n) allow more conformational freedom. Conversion of the hydroxy group to its carboxylic ester reduces the population of conformer ga so that, for R(1) = Pr-n, conformers go and ag are approximately equally populated. The presence of metal salts in the acetone-d(6) solutions causes an increase in the population of conformer ga in both (2-hydroxyalkyl)phosphonates and their carboxylic ester derivatives. The chemical shift difference between the diastereotopic alpha-methylene protons has been shown to be proportional to the population of conformer ga.
• Phillips, A. M. M. M.; Mphahlele, M. J.; Modro, A. M., Phosphorus, Sulfur and Silicon and the Related Elements, 1992, vol. 71, p. 165 - 174
  作者：Phillips, A. M. M. M.、Mphahlele, M. J.、Modro, A. M.、Modro, T. A.、Zwierzak, A.

  DOI：——

  日期：——
• Gajda, T.; Nowalinska, M.; Zawadzki, S., Phosphorus, Sulfur and Silicon and the Related Elements, 1995, vol. 105, # 1-4, p. 45 - 50
  作者：Gajda, T.、Nowalinska, M.、Zawadzki, S.、Zwierzak, A.

  DOI：——

  日期：——
• ( S )-Naproxen® and ( S )-Ibuprofen® chlorides—convenient chemical derivatizing agents for the determination of the enantiomeric excess of hydroxy and aminophosphonates by 31 P NMR
  作者：Katarzyna Błażewska、Tadeusz Gajda

  DOI：10.1016/s0957-4166(02)00186-6

  日期：2002.5

  The acid chlorides of (S)-Naproxen(R) and (S)-lbuprofen(R) are shown to be convenient chiral derivatizing agents for determination of the enantiomeric purity of diethyl 1-hydroxy- and 2-hydroxyalkylphosphonates as well as their aminoalkylphosphonate analogues by means of P-31 NMR spectroscopy. Correlation between the phosphorus chemical shift and the absolute configuration of the 1-hydroxyalkylphosphonate is also discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Preparation and reactivity of β-zinc and copper phosphonates
  作者：Carole Retherford、Tso-Sheng Chou、Robert M. Schelkun、Paul Knochel

  DOI：10.1016/s0040-4039(00)98798-7

  日期：1990.1