Rare-earth metal arylamine group compound as well as preparation method and application thereof

A technology of amino compounds and rare earth metals, applied in the field of rare earth metal aryl amino compounds and their preparation and application, to achieve the effects of convenient product purification, wide applicability, and clear structure

CN103626806AInactive Publication Date: 2014-03-12SUZHOU UNIV
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Publication Date
2014-03-12
Estimated Expiration
Not applicable · inactive patent
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Abstract

The invention discloses a rare-earth metal arylamine group compound as well as preparation method and application thereof. The invention discloses the rare-earth metal arylamine group compound which is characterized in that a general formula of the rare-earth metal arylamine group compound is (2,6-R12PhNH)5LnLi2(THF)2, wherein Ln is a rear-earth metal selected from one of neodymium, samarium, ytterbium or yttrium; R1 is selected from one of hydrogen, methyl or isopropyl. The rare-earth metal arylamine group compound has the advantages that the rare-earth metal arylamine group compound has a definite structure; raw materials used in the preparation method are simple, easily obtained and cheap; the reaction process is simple and easily operated; the rare-earth metal arylamine group compound product is conveniently purified and the yield of the product is high; the rare-earth metal arylamine group compound has a high activity when acting as a single component catalyst to catalyze a hydrogen phosphine reaction of aldehyde or ketone and phosphite ester; the use amount of the catalyst is less; the yield is high; a substrate has wide universality; a new and simple method is provided for synthesis of a-hydroxyphosphonate.
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Description

technical field

[0001] The invention relates to a rare earth metal arylamide compound, a preparation method and application thereof. Background technique

[0002] In the past two decades, the application of phosphorus-containing organic compounds, especially the derivatives of α-hydroxyphosphonate and α-hydroxyphosphoric acid, in medicinal chemistry has attracted a lot of attention. Studies have shown that α-hydroxyphosphonic acid compounds have multiple Such biological activities can be used as insecticides, antibiotics, anticancer agents, antiviral agents and enzyme inhibitors, etc. Therefore, it is of great theoretical and practical significance to study efficient synthesis methods of α-hydroxyphosphonates.

[0003] There are many methods for synthesizing α-hydroxyphosphate, and the Pudovik reaction is undoubtedly the synthesis route that meets the requirements of green chemistry and atom economy. Therefore, this reaction route has received a lot of attention for decades....

Examples

Embodiment 1

[0041] Embodiment one: preparation (2,6-R 1 2 PhNH) 5 Y Li 2 (THF) 2 (R 1 selected from isopropyl):

[0042] (1) Preparation of 2,6-R 1 2 PhNHLi: adding a tetrahydrofuran solution of n-butyl lithium (14.05 mmol) into a tetrahydrofuran solution of an arylamine compound (14.05 mmol) and reacting for 1 to 3 hours to obtain lithium arylamide.

[0043] (2) 2,6-R 1 2 A THF solution of PhNHLi (14.05 mmol) was added to YCl 3 (0.55g, 2.81mmol) of tetrahydrofuran suspension, stirred at 50°C for about 10 hours, the system turned into a light yellow transparent solution, removed tetrahydrofuran under reduced pressure, added 10mL toluene for extraction twice, centrifuged to remove a little precipitate, and transferred the supernatant , concentrated, and stood at room temperature until colorless crystals precipitated, 2.54 g, yield 80%. Elemental analysis: C, 65.80; H, 8.794; N, 5.772; C68 h 106 Li 2 N 2 o 2 Theoretical value of Y: C, 72.38; H, 9.47; N, 6.21; infrared spectru...

Embodiment 2

[0044] Embodiment two: preparation (2,6-R 1 2 PhNH) 5 SmL 2 (THF) 2 (R 1 selected from isopropyl):

[0045] (1) Preparation of 2,6-R 1 2 PhNHLi: adding a tetrahydrofuran solution of n-butyl lithium (14.05 mmol) into a tetrahydrofuran solution of an arylamine compound (14.05 mmol) and reacting for 1 to 3 hours to obtain lithium arylamide.

[0046] (2) 2,6-R 1 2 A THF solution of PhNHLi (14.61 mmol) was added to SmCl 3 (0.75g, 2.92mmol) in tetrahydrofuran suspension, stirred at 50°C for about 10 hours, the system turned into a light yellow transparent solution, removed THF under reduced pressure, added 10mL toluene for extraction twice, centrifuged to remove a little precipitate, and transferred the supernatant , concentrated, and stood at room temperature until light yellow crystals were precipitated, 2.64 g, yield 76%. Elemental analysis: C, 63.22; H, 8.879; N, 6.141; C 68 h 106 Li 2 N 2 o 2 Sm. Theoretical value: C, 68.64; H, 8.98; N, 5.89; infrared spectrum (...

Embodiment 3

[0047] Embodiment three: preparation (2,6-R 1 2 PhNH) 5 NdL 2 (THF) 2 (R 1 selected from isopropyl):

[0048] (1) Preparation of 2,6-R 1 2 PhNHLi: adding a tetrahydrofuran solution of n-butyl lithium (14.05 mmol) into a tetrahydrofuran solution of an arylamine compound (14.05 mmol) and reacting for 1 to 3 hours to obtain lithium arylamide.

[0049] (2) 2,6-R 1 2 A THF solution of PhNHLi (15.96mmol) was added to NdCl 3 (0.80g, 3.19mmol) of tetrahydrofuran suspension, stirred and reacted at 50°C for about 10 hours, the system became a light yellow transparent solution, removed THF under reduced pressure, added 10mL toluene for extraction twice, centrifuged to remove a little precipitate, and transferred the supernatant , concentrated, and stood at room temperature until a light blue crystal precipitated, 2.83 g, yield 75%. Elemental analysis: C, 66.26; H, 8.787; N, 5.395; C 68 h 106 Li 2 N 2 o 2 Nd. Theoretical value: C, 69.00; H, 9.03; N, 5.92; infrared spectrum...