diethyl isobutyryl phosphonate | 1523-69-9

• 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 isobutyryl phosphonate
• 英文别名: diethyl isobutyrylphosphonate；isobutyryl-phosphonic acid diethyl ester；Isobutyryl-phosphonsaeure-diaethylester；Isobutyrylphosphonsaeure-diethylester；Isovalerylphosphonsaeurediethylester；Diaethyl-isobutyryl-phosphonat；Phosphonic acid, (2-methyl-1-oxopropyl)-, diethyl ester；1-diethoxyphosphoryl-2-methylpropan-1-one
• CAS: 1523-69-9
• 化学式: C₈H₁₇O₄P
• 分子量: 208.194
• InChiKey: BVJNLROKHOYRDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  6
• 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：

  diethyl isobutyryl phosphonate 在 sodium tetrahydroborate 、 盐酸羟胺 、 molybdenum(VI) oxide 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 6.0h， 生成 diethyl 1-amino-2-methylpropylphosphonate
  参考文献：
  名称：

  A simple synthesis of 1-aminophosphonic acids from 1-hydroxyiminophosphonates with NaBH4 in the presence of transition metal compounds

  摘要：

  A new procedure has been developed for the synthesis of 1-aminophosphonic acids. Diethyl phosphonates are converted to hydroxyiminophosphonates when treated with hydroxylamine hydrochloride. Reduction of hydroxyiminophosphonates with NaBH4 in MeOH in the presence of MoO3 or NiCl2 and hydrolysis of 1- aminophosphonates gave 1-aminophosphonic acids in good yield.

  DOI：

  10.1016/0040-4039(95)02171-x
• 作为产物：
  描述：

  1-二乙氧基磷酰-2-甲基丙烷-1-醇 在 zinc dichromate(VI) 作用下， 以92%的产率得到diethyl isobutyryl phosphonate
  参考文献：
  名称：

  通过在无溶剂条件下用重铬酸锌三水合物（ZnCr 2 O 7 ·3H 2 O）氧化α-羟基膦酸酯来高产率地制备α-酮膦酸酯

  摘要：

  通过三水合重铬酸锌在无溶剂条件下以高收率和高产率将各种类型的α-羟基膦酸酯转化为α-酮膦酸酯。

  DOI：

  10.1016/s0040-4039(01)00712-2

文献信息

• Nicotinium Dichromate (=3-Carboxypyridinium Dichromate; NDC) as an Efficient Reagent for the Oxidative Deamination of Amines and Aminophosphonates
  作者：Sara Sobhani、Sima Aryanejad、Mahdi Faal Maleki

  DOI：10.1002/hlca.201100404

  日期：2012.4

  A new method for the efficient synthesis of aldehydes, ketones, and oxophosphonates from various types of amines (primary and secondary) and aminophosphonates via oxidative deamination by nicotinium dichromate (=3‐carboxypyridinium dichromate; NDC) is described.

  用于从多种类型的胺（伯和仲）和氨基膦酸盐醛，酮，和oxophosphonates的有效合成的新方法通过被描述;氧化脱氨通过nicotinium重铬酸（NDC = 3-羧基吡啶基重铬酸盐）。
• Oxidative Deamination of α-Aminophosphonates and Amines by Zinc Dichromate Trihydrate (ZnCr2O7˙3H2O) under Solvent-Free Conditions at Room Temperature
  作者：Sara Sobhani、Mahdi Maleki

  DOI：10.1055/s-0029-1219174

  日期：2010.2

  A novel method for the rapid and efficient conversion of a variety ot α-aminophosphonates to α-ketophosphonates using ZnCr 2 O 7 ·3H 2 O via oxidative deamination under solvent-free conditions at room temperature is described. This method is also applicable to the rapid and highly selective oxidation of various types of ordinary amines (primary and secondary) to aldehydes and ketones in good to high

  描述了一种使用 ZnCr 2 O 7 ·3H 2 O 在室温下无溶剂条件下通过氧化脱氨基快速有效地将多种 α-氨基膦酸酯转化为 α-酮膦酸酯的新方法。该方法也适用于各种类型的普通胺（伯胺和仲胺）以良好到高产率快速和高选择性氧化成醛和酮。
• Dialkyl acylphosphonates: a new acylating agent of alcohols
  作者：Mitsuo Sekine、Akiko Kume、Tsujiaki Hata

  DOI：10.1016/s0040-4039(01)81975-4

  日期：1981.1

  Diethyl benzoylphosphonate (1) underwent facile benzoylation of alcohols in the presence of DBU. Reactions of diols containing primary and secondary hydroxyl groups with 1 gave predominantly monobenzoates in which primary hydroxyl groups were highly selectively benzoylated. Related acylations were also described.

  在DBU存在下，苯甲酸二乙酯二乙酯（1）进行了醇的轻松苯甲酰化。含有伯羟基和仲羟基的二醇与1的反应主要产生一苯甲酸酯，其中伯羟基被高度选择性地苯甲酰化。还描述了相关的酰化作用。
• A NEW METHOD FOR ACYLATION OF ENOLATES BY MEANS OF DIALKYL ACYLPHOSPHONATES AS ACYLATING AGENTS
  作者：Mitsuo Sekine、Akiko Kume、Masashi Nakajima、Tsujiaki Hata

  DOI：10.1246/cl.1981.1087

  日期：1981.8.5

  Acylations of various enolates by means of diethyl acylphosphonates were described. For the acylation of acetophenone, lithium bis(trimethylsilyl)amide (LSA) was found to be suitable as the base. The scope and limitation of the benzoylation using diethyl benzoylphosphonates were also described.

  描述了通过酰基膦酸二乙酯对各种烯醇化物的酰化。对于苯乙酮的酰化，发现双（三甲基甲硅烷基）氨基锂（LSA）适合作为碱。还描述了使用苯甲酰膦酸二乙酯进行苯甲酰化的范围和限制。
• Non-hydrolysable analogues of inorganic pyrophosphate as inhibitors of hepatitis C virus RNA-dependent RNA-polymerase
  作者：D. V. Yanvarev、A. N. Korovina、N. N. Usanov、S. N. Kochetkov

  DOI：10.1134/s1068162012020124

  日期：2012.3

  Inorganic pyrophosphate (PPi) is the product of the polymerization reaction catalyzed by DNA- and RNA-polymerases. A number of novel non-hydrolsable PPi analogues was synthesized; some of them inhibited the polymerization reaction catalyzed by hepatitis C virus RNA-dependent RNA-polymerase (NS5B). A new pharmacophore based on a non-hydrolysable methylenediphosphonate backbone has been developed. The

  无机焦磷酸盐 (PPi) 是由 DNA 和 RNA 聚合酶催化的聚合反应产物。合成了许多新型的不可水解的 PPi 类似物；其中一些抑制了丙型肝炎病毒 RNA 依赖性 RNA 聚合酶 (NS5B) 催化的聚合反应。已开发出基于不可水解的亚甲基二膦酸酯骨架的新药效团。介绍了 12 种双膦酸盐的构效关系分析，并说明了对 NS5B 聚合酶活性抑制至关重要的结构特征。