1-二甲氧基磷酰基-2-(4-甲氧基苯基)乙酮 | 87600-56-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-二甲氧基磷酰基-2-(4-甲氧基苯基)乙酮
• 英文名称: Phosphonic acid, [(4-methoxyphenyl)acetyl]-, dimethyl ester
• 英文别名: 1-dimethoxyphosphoryl-2-(4-methoxyphenyl)ethanone
• CAS: 87600-56-4
• 化学式: C₁₁H₁₅O₅P
• 分子量: 258.211
• InChiKey: RTWVMLDKXDMHRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  1-二甲氧基磷酰基-2-(4-甲氧基苯基)乙酮 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
  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：

  对甲氧基苯乙酸 在 草酰氯 作用下， 反应 1.0h， 生成 1-二甲氧基磷酰基-2-(4-甲氧基苯基)乙酮
  参考文献：
  名称：

  单齿亚磷酰胺 的Rh（i）配合物催化α-或β-酰氧基α，β-不饱和膦酸酯的不对称氢化† ‡

  摘要：

  已经公开了带有伯胺部分（DpenPhos）的单齿亚磷酰胺的Rh（I）配合物对于多种α-或β-酰氧基α，β-不饱和膦酸酯的不对称氢化非常有效，从而提供了相应的生物学作用。重要的具有出色对映选择性（90-> 99％ee）的手性α-或β-羟基膦酸衍生物。

  DOI：

  10.1039/c1ob06835k

文献信息

• Highly Enantioselective Synthesis of α-Hydroxy Phosphonic Acid Derivatives by Rh-Catalyzed Asymmetric Hydrogenation with Phosphine–Phosphoramidite Ligands
  作者：Dao-Yong Wang、Xiang-Ping Hu、Jia-Di Huang、Jun Deng、Sai-Bo Yu、Zheng-Chao Duan、Xue-Feng Xu、Zhuo Zheng

  DOI：10.1002/anie.200702924

  日期：2007.10.15
• Facile enolisation of α-ketophosphonates
  作者：Kamyar Afarinkia、Juan Echenique、Stanley C. Nyburg

  DOI：10.1016/s0040-4039(97)00157-3

  日期：1997.3

  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.
• Organocatalyzed asymmetric Michael reaction of β-aryl-α-ketophosphonates and nitroalkenes
  作者：Jie Guang、John Cong-Gui Zhao

  DOI：10.1016/j.tetlet.2013.08.015

  日期：2013.10

  The first enantioselective Michael reaction of beta-aryl-alpha-ketophosphonates and nitroalkenes has been realized by using a new bifunctional Takemoto-type thiourea catalyst. The primary Michael adducts obtained were converted in situ to the corresponding amides through the aminolysis. High yields, excellent diaste-reoselectivities (>95:5 dr), and good enantioselectivities (up to 81% ee) have been achieved for the corresponding oc,13-disubstituted gamma-nitroamides. This reaction again demonstrated that alpha-ketophosphonates are interesting pronucleophiles that can be used as amide surrogates in organocatalyzed reactions. (C) 2013 Elsevier Ltd. All rights reserved.
• Asymmetric hydrogenation of α- or β-acyloxy α,β-unsaturated phosphonates catalyzed by a Rh(i) complex of monodentate phosphoramidite
  作者：Jinzhu Zhang、Kaiwu Dong、Zheng Wang、Kuiling Ding

  DOI：10.1039/c1ob06835k

  日期：——

  The Rh(I) complex of a monodentate phosphoramidite bearing a primary amine moiety (DpenPhos) has been disclosed to be highly efficient for the asymmetric hydrogenation of a variety of α- or β-acyloxy α,β-unsaturated phosphonates, providing the corresponding biologically important chiral α- or β-hydroxy phosphonic acid derivatives with excellent enantioselectivities (90–>99% ee).

  已经公开了带有伯胺部分（DpenPhos）的单齿亚磷酰胺的Rh（I）配合物对于多种α-或β-酰氧基α，β-不饱和膦酸酯的不对称氢化非常有效，从而提供了相应的生物学作用。重要的具有出色对映选择性（90-> 99％ee）的手性α-或β-羟基膦酸衍生物。
• Enantioselective Synthesis of α-Hydroxy and α-Amino Phosphonates via Catalytic Asymmetric Hydrogenation
  作者：Mark J. Burk、Timothy A. Stammers、Judith A. Straub

  DOI：10.1021/ol9906099

  日期：1999.8.1

  [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.