methyl 3-(diethoxyphosphoryl)butanoate | 63201-72-9

• 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 3-(diethoxyphosphoryl)butanoate
• 英文别名: methyl 3-diethoxyphosphorylbutanoate
• CAS: 63201-72-9
• 化学式: C₉H₁₉O₅P
• 分子量: 238.221
• InChiKey: JCZIZOCGOQNCPH-UHFFFAOYSA-N

物化性质

• 沸点：
  306.2±25.0 °C(Predicted)
• 密度：
  1.093±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  methyl 3-(diethoxyphosphoryl)butanoate 在 氨 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以79%的产率得到(2-Carbamoyl-1-methyl-ethyl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  Wasielewski, C.; Topolski, M.; Dembkowski, L., Journal fur praktische Chemie (Leipzig 1954), 1989, vol. 331, # 3, p. 507 - 510

  摘要：

  DOI：
• 作为产物：
  描述：

  巴豆酸甲酯 、 亚磷酸二乙酯 在 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine supported on polystyrene 作用下， 反应 24.0h， 以52%的产率得到methyl 3-(diethoxyphosphoryl)butanoate
  参考文献：
  名称：

  PS-BEMP作为弱电子烯烃中磷-迈克尔加成反应的基本催化剂†

  摘要：

  PS-BEMP用作非均相催化剂，用于将磷亲核体的磷-迈克尔加成到各种电子贫乏的烯烃中。加成反应通常在无溶剂条件下用等摩尔量的试剂进行。事实证明，该方案对于添加芳族，非芳族和环状酮非常有效，在所有情况下均具有良好的收率（78-85％）。该方案还扩展到了α，β-不饱和酯和腈，并获得了良好的结果。这表明PS-BEMP是将磷-迈克尔加成至电子贫乏烯烃的良好催化剂。

  DOI：

  10.1039/c6ob00242k

文献信息

• Tetramethylguanidine (TMG)-catalyzed addition of dialkyl phosphites to α,β-unsaturated carbonyl compounds, alkenenitriles, aldehydes, ketones and imines
  作者：Daniele Simoni、Francesco Paolo Invidiata、Monica Manferdini、Ilaria Lampronti、Riccardo Rondanin、Marinella Roberti、Gian Piero Pollini

  DOI：10.1016/s0040-4039(98)01656-6

  日期：1998.10

  Tetramethylguanidine-catalyzed addition of dialkyl phosphites to α,β-unsaturated carbonyl compounds, alkenenitriles, aldehydes and ketones constitutes a practical route to a variety of phosphonate synthons. The very mild conditions employed, together with the short reaction times, make the procedure highly versatile and tolerant to a range of functionalities. The proposed methodology is also convenient

  四甲基胍催化的亚磷酸二烷基酯向α，β-不饱和羰基化合物，烯基腈，醛和酮的加成构成了各种膦酸酯合成子的实用途径。所采用的非常温和的条件以及较短的反应时间使该方法具有高度的通用性，并能耐受多种功能。所提出的方法对于制备α-氨基膦酸酯也很方便。
• Studies on the free radical carbon-carbon bond formation in the reaction of α-phosphoryl sulfides and selenides with alkenes
  作者：Piotr Bałczewski、Witold M. Pietrzykowski、Marian Mikołlajczyk

  DOI：10.1016/0040-4020(95)00393-m

  日期：1995.7

  alpha-Mono- and alpha, alpha-disubstituted alpha-phosphoryl radicals 9 were generated from the easy accessible alpha-phosphoryl sulfides 4, 5 and alpha-phosphoryl selenides 11, 12 and reacted with the electron rich alkenes 6 under the reductive (n-Bu(3)SnH/AIBN) conditions to give the functionalized phosphonates 7 in 32 divided by 68% yield. Two fragmentation processes of the phosphonate a-alkoxy alkyl radicals are also described.
• 1,5,7-Triazabicyclo[4.4.0]dec-1-ene (TBD), 7-methyl-TBD (MTBD) and the polymer-supported TBD (P-TBD): three efficient catalysts for the nitroaldol (Henry) reaction and for the addition of dialkyl phosphites to unsaturated systems
  作者：Daniele Simoni、Riccardo Rondanin、Massimo Morini、Riccardo Baruchello、Francesco Paolo Invidiata

  DOI：10.1016/s0040-4039(99)02340-0

  日期：2000.3

  The 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) and its 7-methyl derivative (MTBD) have been proven to be of great synthetic utility as catalysts in the nitroaldol (Henry) reaction and for the addition of dialkyl phosphites to a variety of carbonyl compounds. The catalysts were in many cases superior to the parent tetramethylguanidine (TMG). In general the reaction proceeds in a few minutes at 0 degrees C. The polymer-supported-TBD (P-TBD) was also proven to be an efficient promoter of the above cited nucleophilic additions. (C) 2000 Elsevier Science Ltd. All rights reserved.
• WASIELEWSKI, C.;TOPOLSKI, M.;DEMBKOWSKI, L., J. PRAKT. CHEM., 331,(1989) N, C. 507-510
  作者：WASIELEWSKI, C.、TOPOLSKI, M.、DEMBKOWSKI, L.

  DOI：——

  日期：——
• LOPES, LOUSA;MIYATA, YUKINO;KOROLKOVAS, ANDREJUS, REV. FARM. E BIOQUIM. UNIV. SAO PAULO, 26,(1990) N, C. 35-52
  作者：LOPES, LOUSA、MIYATA, YUKINO、KOROLKOVAS, ANDREJUS

  DOI：——

  日期：——