Dimethyl (1-oxobutyl)phosphonate | 64150-99-8

• 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: Dimethyl (1-oxobutyl)phosphonate
• 英文别名: Dimethyl butanoylphosphonate；1-dimethoxyphosphorylbutan-1-one
• CAS: 64150-99-8
• 化学式: C₆H₁₃O₄P
• 分子量: 180.141
• InChiKey: XPSXEKWPLDGUPP-UHFFFAOYSA-N

物化性质

• 沸点：
  211.0±23.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  Dimethyl (1-oxobutyl)phosphonate 在 [((S,S)-Me-DuPHOS)Rh(COD)]OTf 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 25.0 ℃ 、405.33 kPa 条件下， 反应 2.25h， 生成 ((S)-1-Hydroxy-butyl)-phosphonic acid dimethyl ester
  参考文献：
  名称：

  Enantioselective Synthesis of α-Hydroxy and α-Amino Phosphonates via Catalytic Asymmetric Hydrogenation

  摘要：

  [GRAPHICS]Cationic rhodium catalysts of the C-2 symmetric DuPHOS (1) and BPE (2) ligands have demonstrated the ability to asymmetrically hydrogenate a novel series of enol phosphonates (3) in good to excellent enantiomeric excess under mild conditions. Initial studies toward the catalytic asymmetric hydrogenation of enamido phosphonates (6 and 7) using the DuPHOS-Rh+ catalysts are also reported.

  DOI：

  10.1021/ol9906099
• 作为产物：
  描述：

  丁酰氯 、 三甲氧基磷 以 乙醚 为溶剂， 以23%的产率得到Dimethyl (1-oxobutyl)phosphonate
  参考文献：
  名称：

  Facile enolisation of α-ketophosphonates

  摘要：

  A number of alpha-ketophosphonate are prepared and shown to he easily enolised. An X-ray crystal structure determination of a beta-phenyl-alpha-ketophosphonate shows the molecule to be present as hydrogen bonded dimers and demonstrates the presence of enol tautomer in solid state. alpha-ketophosphonate can be converted to the corresponding enolacetate under mild conditions. The enolacetate have the E-configuration exclusively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00157-3

文献信息

• Expeditious, Metal-Free, Domino, Regioselective Synthesis of Highly Substituted 2-Carbonyl- and 2-Phosphorylfurans by Formal [3+2] Cycloaddition
  作者：Wilfried Raimondi、Daniel Dauzonne、Thierry Constantieux、Damien Bonne、Jean Rodriguez

  DOI：10.1002/ejoc.201201192

  日期：2012.11

  the dual electrophilic properties of (2-chloro-2-nitroethenyl)benzenes in a one-pot, formal [3+2] cycloaddition. Using a base (DBU), the desired trisubstituted heterocycles were formed rapidly (10–30 min) in good to excellent yields (51–92 %), and this versatile, metal-free methodology was applied to the synthesis of 2-acyl- and 2-carboalkoxyfurans and furan-2-carboxamides. Additionally, by using 2-ketophosphonate

  通过利用 1,2-二羰基的双重亲核特性和（2-氯-2-硝基乙烯基）苯的双重亲电特性，在一锅正式 [3+2] 环加成反应中，可以很容易地合成 2-官能化呋喃。使用碱 (DBU)，所需的三取代杂环以良好到极好的产率 (51–92%) 快速（10–30 分钟）形成，这种多功能、无金属的方法用于合成 2-酰基-和 2-carboalkoxyfurans 和 furan-2-carboxamides。此外，通过使用 2-酮膦酸酯衍生物作为双亲核试剂，相应的 2-磷酰呋喃以良好的产率 (53–74%) 形成。
• Studies on Organophosphorus Compounds, 53: A New Procedure for the Synthesis of 1-Alkyl or 1-Aryl-1-hydroxy-2-nitroethylphoshonates under PTC Conditions
  作者：Chengye Yuan、Shuhua Cui、Guohong Wang、Hanzhen Feng、Deliang Chen、Chaozhong Li、Yixiang Ding、Ludwig Maier

  DOI：10.1055/s-1992-26081

  日期：——

  A series of dialkyl 1-alkyl- or 1-aryl-1-hydroxy-2-nitroethyl-phosphonates and 1-hydroxy-1-(nitromethyl)alkylphosphonates was prepared by nucleophilic addition of nitromethane to dialkyl acylphosphonates in the presence of potassium carbonate and tetrabutylammonium bromide.

  通过在碳酸钾和四丁基溴化铵的存在下，对二烷基酰基磷酸盐进行硝基甲烷的亲核加成，制备了一系列二烷基1-烷基或1-芳基-1-羟基-2-硝基乙基磷酸酯和1-羟基-1-(硝基甲基)烷基磷酸酯。
• 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。
• Method of preparing oligomers of conjugated dienes with an iron-based catalyst composition
  申请人：Bridgestone Corp.

  公开号：US20030073570A1

  公开（公告）日：2003-04-17

  A catalyst composition that is the combination of or the reaction product of ingredients comprising (a) (i) a halogen-containing iron compound or (ii) an iron-containing compound and a halogen-containing compound, (b) an &agr;-acylphosphonate diester, and (c) an organoaluminum compound.

  一种催化剂组合物，它是由以下成分的组合或反应产物组成的：(a) (i) 含卤素的铁化合物或 (ii) 含铁化合物和含卤素的化合物，(b) &agr;-酰基膦酸二酯，和 (c) 有机铝化合物。
• Iron-based catalyst composition for the manufacture of syndiotactic 1, 2-polybutadiene
  申请人：Bridgestone Corp.

  公开号：US20030073790A1

  公开（公告）日：2003-04-17

  A catalyst composition that is the combination of or the reaction product of ingredients comprising (a) an iron-containing compound, (b) an &agr;-acylphosphonate diester, and (c) an organoaluminum compound.

  一种催化剂组合物，它是由以下成分组成的组合物或反应产物：(a) 含铁化合物；(b) 乙酰基膦酸二酯；(c) 有机铝化合物。