diethyl (1-oxo-3-methylbutyl)phosphonate | 19934-91-9

• 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-oxo-3-methylbutyl)phosphonate
• 英文别名: Isovalerylphosphonsaeurediethylester；Diethylvalerylphosphonat；Phosphonic acid, (3-methyl-1-oxobutyl)-, diethyl ester；1-diethoxyphosphoryl-3-methylbutan-1-one
• CAS: 19934-91-9
• 化学式: C₉H₁₉O₄P
• 分子量: 222.221
• InChiKey: SXXQSRHDNGFMGW-UHFFFAOYSA-N

物化性质

• 沸点：
  122-123 °C(Press: 10 Torr)
• 密度：
  1.0369 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  diethyl (1-oxo-3-methylbutyl)phosphonate 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 α-Hydroxyimino-γ-methyl-butylphosphonsaeurediethylester
  参考文献：
  名称：

  Enantioselective Synthesis of Quaternary α-Aminophosphonates via Conjugate Addition of α-Nitrophosphonates to Enones

  摘要：

  Enantioselective Michael addition of alpha-nitrophosphonates to enones for the synthesis of alpha-aminophosphonates is reported for the first time. The reaction proceeds in good to high yields and moderate to high selectivity in the presence of a new quinine thiourea catalyst. The quaternary nitrophosphonates were conveniently transformed to cyclic quaternary alpha-aminophosphonates via in situ reduction intramolecular cyclization or Baeyer-Villiger oxidation followed by in situ reduction intramolecular cyclization.

  DOI：

  10.1021/ol203132h
• 作为产物：
  描述：

  异戊酰氯 、 亚磷酸三乙酯 生成 diethyl (1-oxo-3-methylbutyl)phosphonate
  参考文献：
  名称：

  [EN] COMPOSITIONS USEFUL IN THERAPY OF AUTOPHAGY-RELATED PATHOLOGIES, AND METHODS OF MAKING AND USING THE SAME
  [FR] COMPOSITIONS UTILES EN THÉRAPIE DE PATHOLOGIES LIÉES À L'AUTOPHAGIE, ET LEURS PROCÉDÉS DE FABRICATION ET D'UTILISATION

  摘要：

  兰硫氨酸酮亚胺磷酸酯（LK-P）、兰硫氨酸酮亚胺酯磷酸酯（LKE-P）、其他兰硫氨酸酮亚胺、兰硫氨酸酮亚胺磷酸酯以及兰硫氨酸酮亚胺酯衍生物的制备和使用方法被描述。

  公开号：

  WO2018156429A1

文献信息

• Preparation of α-ketophosphonates by a [3,3]-sigmatropoic shift of enolphosphonates
  作者：Kamyar Afarinkia、Andrew J. Twist、Hiu-wan Yu

  DOI：10.1016/j.jorganchem.2004.10.016

  日期：2005.5

  α-Ketophosphonates are prepared by a [3,3]-sigmatropic shift of enolphosphonates.

  α-酮膦酸酯是通过烯醇膦酸酯的[3,3]-σ位移而制备的。
• [EN] COMPOSITIONS USEFUL IN THERAPY OF AUTOPHAGY-RELATED PATHOLOGIES, AND METHODS OF MAKING AND USING THE SAME<br/>[FR] COMPOSITIONS UTILES EN THÉRAPIE DE PATHOLOGIES LIÉES À L'AUTOPHAGIE, ET LEURS PROCÉDÉS DE FABRICATION ET D'UTILISATION
  申请人：UNIV TOLEDO

  公开号：WO2017147440A1

  公开（公告）日：2017-08-31

  Lanthionine ketimine derivatives, and methods of making and using the same, are described. Included are lanthionine ketimine phosphonate (LK-P), lanthionine ketimine ester phosphonate (LKE-P) derivatives, as well as lanthionine ketimine derivatives having a tert-enamide moiety at the 2-position (NVP-LKE).

  兰硫氨酸酮亚胺衍生物的制备方法和用途被描述。包括兰硫氨酸酮亚胺磷酸酯（LK-P）、兰硫氨酸酮亚胺酯磷酸酯（LKE-P）衍生物，以及在2位点具有叔-烯酰胺基团的兰硫氨酸酮亚胺衍生物（NVP-LKE）。
• Preparation of Asymmetric α-Ketophosphonates by [3,3]-Sigmatropic Shift of Enolphosphonates
  作者：Kamyar Afarinkia、Andrew J. Twist、Hiu-wan Yu

  DOI：10.1021/jo049133j

  日期：2004.9.1

  α-Ketophosphonates are prepared by a [3,3]-sigmatropic shift of enolphosphonates.

  α-酮膦酸酯是通过烯醇膦酸酯的[3,3]-σ位移制备的。
• A novel route to .alpha.-aminoalkylphosphonic acids and dialkyl .alpha.-aminoalkylphosphonate hydrochlorides
  作者：K. Darrell Berlin、N. K. Roy、R. T. Claunch、D. Bude

  DOI：10.1021/ja01018a076

  日期：1968.7
• Enantioselective synthesis of diethyl 1-hydroxyalkylphosphonates via oxazaborolidine catalyzed borane reduction of diethyl α-ketophosphonates
  作者：Tadeusz Gajda

  DOI：10.1016/s0957-4166(00)86271-0

  日期：1994.10

  Reduction of diethyl alpha-ketophosphonates 1 with borane and B-butyloxazaborolidine 2 as catalyst afforded diethyl (S)- or (R)-1-hydroxyalkylphosphonates 3a-d or 3e-f respectively in good yields and moderate to good enantiomeric excess (53-83 ee%). Respective diethyl (R)- and (S)-1-aminoalkylphosphonates 6 were obtained in a one-pot transformation, by the Mitsunobu reaction of 1-hydroxyphosphonates 3 with hydrazoic acid, and subsequent treatment of the intermediate azides 4, with triphenylphosphine, followed by hydrolysis df the iminophosphoranes 5 with water.