1,1-二甲氧基-1-[甲氧基(甲基)磷基]乙烷 | 75164-27-1

• 分子结构分类: 有机化合物 - 有机磷化合物 - 有机膦酸及其衍生物
• 中文名称: 1,1-二甲氧基-1-[甲氧基(甲基)磷基]乙烷
• 英文名称: methyl (1,1-dimethoxyethyl)methylphosphinate
• 英文别名: 1,1-dimethoxy-1-[methoxy(methyl)phosphoryl]ethane
• CAS: 75164-27-1
• 化学式: C₆H₁₅O₄P
• 分子量: 182.156
• InChiKey: WRPXTPOGMVVGQR-UHFFFAOYSA-N

物化性质

• 沸点：
  188.3±50.0 °C(Predicted)
• 密度：
  1.066±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-二甲氧基-1-[甲氧基(甲基)磷基]乙烷 在 sodium iodide 作用下， 以 丙酮 为溶剂， 以37.5%的产率得到sodium acetylmethylphosphinate
  参考文献：
  名称：

  Acetylphosphinate is the most potent mechanism-based substrate-like inhibitor of both the human and Escherichia coli pyruvate dehydrogenase components of the pyruvate dehydrogenase complex

  摘要：

  Two analogues of pyruvate, acetylphosphinate and acetylmethylphosphinate were tested as inhibitors of the E1 (pyruvate dehydrogenase) component of the human and Escherichia coli pyruvate dehydrogenase complexes. This is the first instance of such studies on the human enzyme. The acetylphosphinate is a stronger inhibitor of both enzymes (K-i < 1 mu M) than acetylmethylphosphinate. Both inhibitors are found to be reversible tight-binding inhibitors. With both inhibitors and with both enzymes, the inhibition apparently takes place by formation of a C2 alpha-phosphinolactylthiamin diphosphate derivative, a covalent adduct of the inhibitor and the coenzyme, mimicking the behavior of substrate and forming a stable analogue of the C2 alpha-lactylthiamin diphosphate. Formation of the intermediate analogue in each case is confirmed by the appearance of a positive circular dichroism band in the 305-306 nm range, attributed to the 1',4'-iminopyrimidine tautomeric form of the coenzyme. It is further shown that the alpha His63 residue of the human E1 has a role in the formation of C2 alpha-lactylthiamin diphosphate since the alpha His63Ala variant is only modestly inhibited by either inhibitor, nor did either compound generate the circular dichroism bands assigned to different tautomeric forms of the 4'-aminopyrimidine ring of the coenzyme seen with the wild-type enzyme. Interestingly, opposite enantiomers of the carboligase side product acetoin are produced by the human and bacterial enzymes. (c) 2006 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2006.09.001
• 作为产物：
  描述：

  原乙酸三甲酯 、 甲基二氯膦 生成 1,1-二甲氧基-1-[甲氧基(甲基)磷基]乙烷
  参考文献：
  名称：

  Compounds and compositions

  摘要：

  描述了包含化学式I中一个或多个化合物的杀虫组合物，其中Ra是一个基团R.sup.2或--OR.sup.2，E是氧或硫，Rm是--O.sup..crclbar. M.sup..sym.或--NRyRz，M.sup..sym.是一当量的农业可接受阳离子，R.sup.1和R.sup.2，可能相同也可能不同，分别代表氢、烷基、烯基、炔基或芳基；所述烷基、烯基、炔基或芳基可以选择性地被一个或多个卤素、烷氧基、硝基、烷基、--CF.sub.3、腈基或羧酸或其盐、酯或酰胺取代，Ry和Rz，可能相同也可能不同，分别代表氢或烷基，或其农业可接受的衍生物。还描述了制备和使用化学式I中化合物的方法。

  公开号：

  US04339443A1

文献信息

• Compounds and compositions
  申请人：FBC Limited

  公开号：US04339443A1

  公开（公告）日：1982-07-13

  There are described pesticidal compositions comprising one or more compounds of the formula I, ##STR1## in which Ra is a group R.sup.2 or --OR.sup.2, E is oxygen or sulphur, Rm is --O.sup..crclbar. M.sup..sym. or --NRyRz, M.sup..sym. is one equivalent of an agriculturally acceptable cation, R.sup.1 and R.sup.2, which may be the same or different, each represent hydrogen, alkyl, alkenyl, alkynyl or aryl; the alkyl, alkenyl, alkynyl or aryl optionally being substituted by one or more halogen, alkoxy, nitro, alkyl, --CF.sub.3, nitrile, or carboxylic acid or a salt, ester, or amide thereof, and Ry and Rz, which may be the same or different, each represent hydrogen or alkyl, or an agriculturally acceptable derivative thereof. There are also described methods for making and using compounds of formula I.

  描述了包含化学式I中一个或多个化合物的杀虫组合物，其中Ra是一个基团R.sup.2或--OR.sup.2，E是氧或硫，Rm是--O.sup..crclbar. M.sup..sym.或--NRyRz，M.sup..sym.是一当量的农业可接受阳离子，R.sup.1和R.sup.2，可能相同也可能不同，分别代表氢、烷基、烯基、炔基或芳基；所述烷基、烯基、炔基或芳基可以选择性地被一个或多个卤素、烷氧基、硝基、烷基、--CF.sub.3、腈基或羧酸或其盐、酯或酰胺取代，Ry和Rz，可能相同也可能不同，分别代表氢或烷基，或其农业可接受的衍生物。还描述了制备和使用化学式I中化合物的方法。
• Acetylphosphinate is the most potent mechanism-based substrate-like inhibitor of both the human and Escherichia coli pyruvate dehydrogenase components of the pyruvate dehydrogenase complex
  作者：Natalia S. Nemeria、Lioubov G. Korotchkina、Sumit Chakraborty、Mulchand S. Patel、Frank Jordan

  DOI：10.1016/j.bioorg.2006.09.001

  日期：2006.12

  Two analogues of pyruvate, acetylphosphinate and acetylmethylphosphinate were tested as inhibitors of the E1 (pyruvate dehydrogenase) component of the human and Escherichia coli pyruvate dehydrogenase complexes. This is the first instance of such studies on the human enzyme. The acetylphosphinate is a stronger inhibitor of both enzymes (K-i < 1 mu M) than acetylmethylphosphinate. Both inhibitors are found to be reversible tight-binding inhibitors. With both inhibitors and with both enzymes, the inhibition apparently takes place by formation of a C2 alpha-phosphinolactylthiamin diphosphate derivative, a covalent adduct of the inhibitor and the coenzyme, mimicking the behavior of substrate and forming a stable analogue of the C2 alpha-lactylthiamin diphosphate. Formation of the intermediate analogue in each case is confirmed by the appearance of a positive circular dichroism band in the 305-306 nm range, attributed to the 1',4'-iminopyrimidine tautomeric form of the coenzyme. It is further shown that the alpha His63 residue of the human E1 has a role in the formation of C2 alpha-lactylthiamin diphosphate since the alpha His63Ala variant is only modestly inhibited by either inhibitor, nor did either compound generate the circular dichroism bands assigned to different tautomeric forms of the 4'-aminopyrimidine ring of the coenzyme seen with the wild-type enzyme. Interestingly, opposite enantiomers of the carboligase side product acetoin are produced by the human and bacterial enzymes. (c) 2006 Elsevier Inc. All rights reserved.