methyl-vinyl-phosphinic acid 2-chloro-ethyl ester | 36120-72-6

• 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
• 英文名称: methyl-vinyl-phosphinic acid 2-chloro-ethyl ester
• 英文别名: 2-Chloroethyl methylvinylphosphinate；2-Chloroethylmethylvinylposphinate；Methyl-vinyl-phosphinsaeure-β-chloraethylester；2-Chloroethyl-methyl-vinylphosphinat；Methyl(vinyl)phosphinic acid 2-chloroethylester；1-chloro-2-[ethenyl(methyl)phosphoryl]oxyethane
• CAS: 36120-72-6
• 化学式: C₅H₁₀ClO₂P
• mdl: MFCD19232317
• 分子量: 168.56
• InChiKey: FUKKAIWQJRRCIQ-UHFFFAOYSA-N

物化性质

• 沸点：
  200.5±42.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl-vinyl-phosphinic acid 2-chloro-ethyl ester 、 N-hydroxy-4-methoxybenzenecarboximidoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以0.37 g的产率得到methyl-[3-(4-methoxyphenyl)-4,5-dihydro-isoxazol-5-yl]phosphinic acid 2-chloro-ethyl ester
  参考文献：
  名称：

  Inhibition of the Antibacterial Target UDP-(3-O-acyl)-N-acetylglucosamine Deacetylase (LpxC):  Isoxazoline Zinc Amidase Inhibitors Bearing Diverse Metal Binding Groups

  摘要：

  UDP-3-O-[R-3-hydroxymyristoyl]-GlcNAc deacetylase (LpxC) is a zinc amidase that catalyzes the second step of lipid A biosynthesis in Gram negative bacteria. Known inhibitors of this enzyme are oxazolines incorporating a hydroxamic acid at the 4-position, which is believed to coordinate to the single essential zinc ion. A new structural class of inhibitors was designed to incorporate a more stable and more synthetically. versatile isoxazoline core. The synthetic versatility of the isoxazoline allowed for a broad study of metal binding. groups. Nine of 17 isoxazolines, each incorporating a different potential metal binding functional group, were found to exhibit enzyme inhibitory activity, including one that is more active than the corresponding hydroxamic acid. Additionally, a designed affinity label inhibits LpxC in a time-dependent manner.

  DOI：

  10.1021/jm020183v
• 作为产物：
  描述：

  Methyl-2-chloraethyl-phosphinsaeure-2-chloraethylester 在 三乙胺 作用下， 生成 methyl-vinyl-phosphinic acid 2-chloro-ethyl ester
  参考文献：
  名称：

  Weissermel; Kleiner; Finke, Angewandte Chemie, 1981, vol. 93, # 3, p. 256 - 265

  摘要：

  DOI：

文献信息

• Synthesis of Glufosinate via Amidocarbonylation
  作者：Shinichiro Takigawa、Shuzo Shinke、Masato Tanaka

  DOI：10.1246/cl.1990.1415

  日期：1990.8

  Cobalt carbonyl-catalyzed carbonylation of methylvinylphosphinate with acetamide followed by hydrolysis gave 2-amino-4-[hydroxy(methyl)phosphinyl]butanoic acid (glufosinate) in more than 80% overall yield.

  在羰基钴催化下，乙烯基膦酸甲酯与乙酰胺发生羰基化反应，然后进行水解，得到了 2-氨基-4-[羟基（甲基）膦酰基]丁酸（草胺膦酸），总收率超过 80%。
• Hydroformylation–Amidocarbonylation of Methylvinylphosphinate. Application to Synthesis of Glufosinate
  作者：Toshiyasu Sakakura、Xin-Yan Huang、Masato Tanaka

  DOI：10.1246/bcsj.64.1707

  日期：1991.5

  Glufosinate, 2-amino-4-[(hydroxy)methylphosphinyl]butanoic acid, (2a) was synthesized from 2-chloroethyl methylvinylphosphinate (1a) via successive hydroformylation–amidocarbonylation. Hydroformylation of 1a catalyzed by Co2(CO)8 in methanol gave 2-chloroethyl (3,3-dimethoxypropyl)methylphosphinate (5). Crude 5 was subjected to cobaltcatalyzed amidocarbonylation to afford N-acylglufosinic acid methyl ester (2b). Hydrolysis of 2b under acidic conditions gave 2a quantitatively.

  草铵膦，2-氨基-4-[(羟基)甲基次膦基]丁酸，(2a)是由2-氯乙基甲基乙烯基次膦酸酯(1a)通过连续加氢甲酰化-酰氨基羰基化合成的。 1a 在甲醇中经 Co2(CO)8 催化加氢甲酰化，得到 (3,3-二甲氧基丙基)甲基次膦酸 2-氯乙酯 (5)。将粗品5进行钴催化的酰氨基羰基化，得到N-酰基草铵膦酸甲酯(2b)。 2b在酸性条件下水解定量得到2a。
• Process for producing phosphinylamino acid derivatives
  申请人：NISSAN CHEMICAL INDUSTRIES LTD.

  公开号：EP0292918A1

  公开（公告）日：1988-11-30

  A process for producing a phosphinylamino acid derivative of the formula: wherein R¹ is a lower alkyl group, R² is a hydrogen atom, a lower alkyl group, a halo-lower alkyl group or a substituted or unsubstituted phenyl group, and R³ is a substituted or unsubstituted alkyl group or a substituted or unsubstituted phenyl group, which comprises reacting a compound of the formula: wherin R¹ and R² are as defined above, and/or a compound of the formula: wherein R¹ and R² are as defined above, with a compound of the formula: R³CONH₂      (IV) wherein R³ is as defined above, carbon monoxide and hydrogen in the presence of a catalyst containing a metal of Group VIII of the Periodic Table.

  一种生产式膦酰基氨基酸衍生物的工艺： 其中R¹为低级烷基，R²为氢原子、低级烷基、卤代低级烷基或取代或未取代的苯基，R³为取代或未取代的烷基或取代或未取代的苯基，该工艺包括使式如下化合物反应 其中 R¹ 和 R² 如上定义，和/或一种式化合物： 其中 R¹ 和 R² 如上所定义，与式化合物反应： R³CONH₂ (IV) 其中 R³ 如上定义，一氧化碳和氢在含有元素周期表第八族金属的催化剂存在下。
• Novel organic phosphorous derivatives and manufacturing processes therefor
  申请人：NISSAN CHEMICAL INDUSTRIES LTD.

  公开号：EP0336558A1

  公开（公告）日：1989-10-11

  Novel methyl-3,3′-dialkoxypropylphosphinic acid derivatives of the formula (I), which are useful intermediates for manufacturing herbicidal compounds, were prepared by oxo synthesis of a readily available and inexpensive compound (II). According to amido-carbonylation of the compounds (I), a following compound (V) also useful intermediates for a herbicidal compound was obtained. According to concurrent amido-carbonylation of the compounds (II), the compounds (V) and/or following compounds (VI) also useful intermediates for the herbicidal compound was obtained. R¹ means alkyl, R² means alkyl or phenyl which may be substituted and X means lower alkyl, halo-lower alkyl or phenyl which may be substituted.

  新型甲基-3,3′-二烷氧基丙基膦酸衍生物的式 (I)、 通过对一种容易获得且价格低廉的化合物（II）进行氧代合成，制备出了新型甲基-3,3′-二烷氧基丙基膦酸衍生物，该衍生物是生产除草化合物的有用中间体。 通过对化合物（I）进行酰胺基羰基化，得到了以下化合物（V），它们也是除草化合物的有用中间体。 通过同时对化合物（II）进行酰胺基羰基化，可以得到化合物（V）和/或后续化合物（VI），它们也是除草化合物的有用中间体。 R¹ 表示烷基，R² 表示烷基或可能被取代的苯基，X 表示低级烷基、卤代低级烷基或可能被取代的苯基。
• Weissermel; Kleiner; Finke, Angewandte Chemie, 1981, vol. 93, # 3, p. 256 - 265
  作者：Weissermel、Kleiner、Finke、Felcht

  DOI：——

  日期：——