methyl 2-(methoxy(methyl)phosphoryloxy)-2-methylpropanoate

• 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: methyl 2-(methoxy(methyl)phosphoryloxy)-2-methylpropanoate
• 英文别名: Methyl 2-[methoxy(methyl)phosphoryl]oxy-2-methylpropanoate；methyl 2-[methoxy(methyl)phosphoryl]oxy-2-methylpropanoate
• 化学式: C₇H₁₅O₅P
• 分子量: 210.167
• InChiKey: YTPZDGDOVYFHQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲基氯膦酸甲酯 、 2-羟基异丁酸甲酯 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以65%的产率得到methyl 2-(methoxy(methyl)phosphoryloxy)-2-methylpropanoate
  参考文献：
  名称：

  Synthesis of both RP and SP enantiomers of unsymmetrical methylphosphonates based on a new approach utilizing a P-ester bond with α-hydroxyacids

  摘要：

  Condensation of methyl methylphosphonochloridate with the dilithium salt of 2-methyllactic acid gave P-racemic methylphosphonates which unexpectedly contained two units of alpha-hydroxyacid linked via carboxylic ester bond. The racemic mixture was chromatographically separated via diastereomeric salts with quinine or cinchonine to give, based on the X-ray analysis, pure (R-p)-(+) and (S-p)-(-) enantiomers. Both enantiomers were immobilized on the ArgoGel (R)-OH solid support. Condensation of methyl methylphosphonochloridate with alpha-hydroxyacid methyl esters [2-methyllactate, (S-C)-(-)-lactate, methyl (S-C)-(+) and (R-C)(-)-mandelates] gave chromatographically inseparable 1:1 mixtures of diastereomers in 63-69% yields. A basic hydrolysis of the latter resulted in a selective and unexpected cleavage of the P-OMe group in a quantitative yield [(S-C)-(+) and (R-C)-(-)-mandelates, (S-C) -(-)-lactate] or simultaneous cleavages of P-OMe and C(O)OMe groups (2-methyllactate). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.04.015

文献信息

• NONAQUEOUS ELECTROLYTE SOLUTION AND ELECTROCHEMICAL ELEMENT USING SAME
  申请人：Abe Koji

  公开号：US20120171581A1

  公开（公告）日：2012-07-05

  Disclosed are a nonaqueous electrolytic solution of an electrolyte dissolved in a nonaqueous solvent, which contains a carboxylate represented by the following general formula (I) in an amount of from 0.01 to 10% by mass of the nonaqueous electrolytic solution; and an electrochemical element using it. (In the formula, R 1 represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, or a cyanoalkyl group; R 2 represents a hydrogen atom, an alkoxy group, a formyloxy group, an acyloxy group, an alkoxycarbonyloxy group, an alkanesulfonyloxy group, an arylsulfonyloxy group, an alkylsilyloxy group, a dialkylphosphoryloxy group, an alkoxy(alkyl)phosphoryloxy group, or a dialkoxyphosphoryloxy group; R 3 represents a hydrogen atom, —CH 2 COOR 6 , or an alkyl group; R 4 represents a hydrogen atom or an alkyl group; R 5 has the same meaning as R 2 , or represents a hydrogen atom, an alkyl group, or —CH 2 COOR 7 ; R 6 and R 7 each independently represent an alkyl group, an alkenyl group, an alkynyl group, or a cycloalkyl group; X represents —OR 8 , -A 2 -C≡Y 2 , -A 2 -C(═O)O-A 3 -C≡Y 2 , -A 2 -C(═O)O-A 4 or COOR 1 ; R 5 is the same as R 1 ; A 1 to A 3 each independently represent an alkylene group; A 4 represents an alkyl group; Y 2 represents CH or N; m indicates an integer of from 0 to 4; n indicates 0 or 1.)

  本发明涉及一种非水电解质溶液，其中包含以下述通式（I）表示的羧酸盐，其质量占非水电解质溶液的0.01至10％；以及使用该电解质溶液的电化学元件。（在式中，R1表示烷基、烯基、炔基、环烷基或氰基烷基；R2表示氢原子、烷氧基、甲酰氧基、酰氧基、烷氧羰基氧基、烷基磺酰氧基、芳基磺酰氧基、烷基硅氧基、二烷基磷酰氧基、烷氧（烷基）磷酰氧基或二烷氧基磷酰氧基；R3表示氢原子、-CH2COOR6或烷基；R4表示氢原子或烷基；R5与R2的含义相同，或表示氢原子、烷基或-CH2COOR7；R6和R7各自独立地表示烷基、烯基、炔基或环烷基；X表示-OR8，-A2-C≡Y2，-A2-C（═O）O-A3-C≡Y2，-A2-C（═O）O-A4或COOR1；R5与R1的含义相同；A1至A3各自独立地表示烷基；A4表示烷基；Y2表示CH或N；m表示0至4的整数；n表示0或1。）
• US9130244B2
  申请人：——

  公开号：US9130244B2

  公开（公告）日：2015-09-08
• Synthesis of both RP and SP enantiomers of unsymmetrical methylphosphonates based on a new approach utilizing a P-ester bond with α-hydroxyacids
  作者：Piotr Bałczewski、Aldona Szadowiak、Tomasz Białas、Wanda M. Wieczorek、Agnieszka Balińska

  DOI：10.1016/j.tetasy.2006.04.015

  日期：2006.4

  Condensation of methyl methylphosphonochloridate with the dilithium salt of 2-methyllactic acid gave P-racemic methylphosphonates which unexpectedly contained two units of alpha-hydroxyacid linked via carboxylic ester bond. The racemic mixture was chromatographically separated via diastereomeric salts with quinine or cinchonine to give, based on the X-ray analysis, pure (R-p)-(+) and (S-p)-(-) enantiomers. Both enantiomers were immobilized on the ArgoGel (R)-OH solid support. Condensation of methyl methylphosphonochloridate with alpha-hydroxyacid methyl esters [2-methyllactate, (S-C)-(-)-lactate, methyl (S-C)-(+) and (R-C)(-)-mandelates] gave chromatographically inseparable 1:1 mixtures of diastereomers in 63-69% yields. A basic hydrolysis of the latter resulted in a selective and unexpected cleavage of the P-OMe group in a quantitative yield [(S-C)-(+) and (R-C)-(-)-mandelates, (S-C) -(-)-lactate] or simultaneous cleavages of P-OMe and C(O)OMe groups (2-methyllactate). (c) 2006 Elsevier Ltd. All rights reserved.