2-Methoxy-benzoyl-phosphonsaeure-diaethylester | 16656-43-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Methoxy-benzoyl-phosphonsaeure-diaethylester
• 英文别名: 2-Methoxy-benzoyl-phosphonsaeure-diethylester；Diethoxyphosphoryl-(2-methoxyphenyl)methanone
• CAS: 16656-43-2
• 化学式: C₁₂H₁₇O₅P
• 分子量: 272.238
• InChiKey: QAPJRXOQLZJSAN-UHFFFAOYSA-N

物化性质

• 沸点：
  366.9±44.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Methoxy-benzoyl-phosphonsaeure-diaethylester 在 盐酸 、 对硝基苯酚 、 N-[(8Α,9S)-6'-甲氧基辛可宁-9-基]-N'-(2,3,4,6-四-O-乙酰基-Β-D-吡喃葡萄糖基)硫脲 、 水 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 36.0h， 生成 (S)-diethyl cyano(hydroxy)(2-methoxyphenyl)methylphosphonate
  参考文献：
  名称：

  第三纪的对映选择性合成α-羟基膦酸酯催化由碳水化合物/金鸡纳生物碱硫脲有机催化剂

  摘要：

  一小撮糖：基于双功能碳水化合物/金鸡宁的新型硫脲1是专为α-酮膦酸酯和三甲基甲硅烷基氰化物的不对称加成反应而设计的，它们的产物可以水解得到具有优异对映选择性的叔α-羟基膦酸酯。

  DOI：

  10.1002/anie.201204287

文献信息

• Addition of Trifluoromethyltrimethylsilane to Acyl Phosphonates:  Synthesis of TMS-Protected 1-Alkyl-1-trifluoromethyl-1-hydroxyphosphonates and 1-Aryldifluoroethenyl Phosphates
  作者：Ayhan S. Demir、Serkan Eymur

  DOI：10.1021/jo070913c

  日期：2007.10.1

  Addition reactions of nucleophilic CF3TMS to acyl phosphonates were investigated. Various acyl phosphonates reacted readily with CF3TMS in the presence of K2CO3 in DMF at rt to give 1-alkyl-2,2,2-trifluoro-1-trimethylsilyloxyethylphosphonate in 70-90% yields. When benzoyl phosphonates were used as starting material, after addition of CF3, the formed alcoholate undergoes phosphonate-phosphate rearrangement to form the acyl anion, followed by elimination of F- to give 1-aryldifluoroethenyl phosphates in 87-97% yields. As a representative example, vinylphosphate 6a was converted into 2,2-difluoro-1-phenylethanone 7 with 6 N HC1/EtOH/reflux or CAN/NaOH/MeOH/O degrees C in 82-90% yields.
• Protonation of acyl anion equivalents generated from acylphosphonates: nonhydride access to the aldehyde oxidation state from the carboxylic acid oxidation state
  作者：Ayhan S. Demir、Ömer Reis、Ilker Esiringü、Barbaros Reis、Sehriban Baris

  DOI：10.1016/j.tet.2006.10.036

  日期：2007.1

  Acylphosphonates, which are easily available from carboxylic acids, are potent acyl anion precursors and undergo cyanide ion promoted phosphonate-phosphate rearrangement to provide the corresponding acyl anion equivalents as reactive intermediates. The protonation of these acyl anion equivalents furnished cyanohydrin O-phosphates in good yields. For the high yield formation of cyanohydrin O-phosphates from arylphosphonates THF should be used and from alkylphosphonates DME was used. (c) 2006 Elsevier Ltd. All rights reserved.
• Enantioselective Synthesis of Tertiary α-Hydroxy Phosphonates Catalyzed by Carbohydrate/Cinchona Alkaloid Thiourea Organocatalysts
  作者：Shasha Kong、Weidong Fan、Guiping Wu、Zhiwei Miao

  DOI：10.1002/anie.201204287

  日期：2012.8.27

  A pinch of sugar: The new bifunctional carbohydrate/cinchonine‐based thiourea 1 has been designed for the asymmetric addition reaction of α‐ketophosphonates and trimethylsilyl cyanide, the product of which can be hydrolyzed to afford tertiary α‐hydroxy phosphonates with excellent enantioselectivities.

  一小撮糖：基于双功能碳水化合物/金鸡宁的新型硫脲1是专为α-酮膦酸酯和三甲基甲硅烷基氰化物的不对称加成反应而设计的，它们的产物可以水解得到具有优异对映选择性的叔α-羟基膦酸酯。