Spiro bis (dihydrobenzosilole) phosphonite monoester compound as well as preparation and application thereof

A compound and single-bond technology, applied in the field of spirobisdihydrobenzosilrole phosphonite monoester compounds, can solve the problem of single phosphonite monoester ligands and achieve good enantioselectivity and catalytic High activity, product enantioselectivity, high catalytic activity

Pending Publication Date: 2022-04-08
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is to provide a s...

Method used

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  • Spiro bis (dihydrobenzosilole) phosphonite monoester compound as well as preparation and application thereof
  • Spiro bis (dihydrobenzosilole) phosphonite monoester compound as well as preparation and application thereof
  • Spiro bis (dihydrobenzosilole) phosphonite monoester compound as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0158] Example 1: I-4

[0159]

[0160] Under a nitrogen atmosphere, in a 10 mL dry Schlenk tube, add spirobisdihydrobenzothiazole diol (296.4 mg, 1.0 mmol) and dissolve in 2.0 mL of tetrahydrofuran, add TEA (0.7 mL, 5.0 mmol), room temperature Slowly add diphenylphosphorus chloride (0.7mL, 4.0mmol) under stirring, TLC detects that the reaction is complete, filter with diatomaceous earth, wash with ethyl acetate, and the filtrate is desolventized by a rotary evaporator and purified by column chromatography to obtain the spirochete Bisdihydrobenzosilrole phosphite (531.8 mg, yield: 80%).

[0161]

[0162] white solid, [a] D 24 =+142.87 (c=0.90, CHCl 3 ); 1 H NMR (400MHz, acetone-d 6 )δ7.43–7.32(m,12H),7.17(q,J=3.9Hz,2H),7.09(ddd,J=12.4,6.7,4.7Hz,12H),3.32–3.18(m,2H),1.61 (dd,J=15.1,8.4Hz,2H),1.24(d,J=7.0Hz,6H),0.81(dd,J=15.1,4.0Hz,2H). 31 P NMR (162MHz, acetone-d 6 )δ102.02. HRMS (ESI-TOF) m / z calculated value C 42 h 38 o 2 P 2 Si[M+H] + :665.2116, test value...

Embodiment 2

[0163] Example 2: I-3

[0164]

[0165] White solid, 77% yield, [a] D 24 =-142.87 (c=0.90, CHCl 3 ); 1 H NMR (400MHz, acetone-d 6 )δ7.43–7.32(m,12H),7.17(q,J=3.9Hz,2H),7.09(ddd,J=12.4,6.7,4.7Hz,12H),3.32–3.18(m,2H),1.61 (dd,J=15.1,8.4Hz,2H),1.24(d,J=7.0Hz,6H),0.81(dd,J=15.1,4.0Hz,2H). 13 C NMR (100MHz, chloroform-d) δ162.18, 154.17, 132.78, 127.72, 122.97, 120.21, 40.12, 25.52, 5.96; 31 P NMR (162MHz, acetone-d 6 )δ102.02. HRMS (ESI-TOF) m / z calculated value C 18 h 20 o 4 SiP[M+H] + : 359.0863, test value: 359.0863. HRMS (ESI-TOF) m / z calculated value C 42 h 38 o 2 P 2 Si[M+H] + :665.2116, test value: 665.2196.

Embodiment 3

[0166] Example 3: I-1

[0167]

[0168] White solid, 87% yield, [a] D 24 =-159.87 (c=0.90, CHCl 3 ); 1 H NMR (400MHz, acetone-d 6 )δ7.35(dt, J=10.9,7.3Hz,12H),7.22–7.06(m,12H),6.99(d,J=7.5Hz,2H),3.00(dddd,J=31.5,17.1,9.5, 5.3Hz, 4H), 1.29(ddd, J=15.6, 9.7, 6.0Hz, 2H), 1.14(ddd, J=14.9, 9.3, 4.7Hz, 2H).; 13 C NMR (101MHz, acetone-d 6 )δ161.02,160.93,157.07,140.93,140.75,140.62,140.45,132.19,132.17,130.74,130.50,129.93,129.37,129.15,129.00,128.47,128.40,128.36,128.29,126.35,120.16,112.32,112.09,31.43,8.69 . 31 P NMR (162MHz, acetone-d 6 )δ101.02. HRMS (ESI-TOF) m / z calculated value C 40 h 34 o 2 P 2 Si[M+H] + :637.1803, test value: 637.1859.

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Abstract

The invention discloses a spirobidihydrobenzosilole phosphorous acid monoester compound as well as a preparation method and application of the spirobidihydrobenzosilole phosphorous acid monoester compound. The invention specifically discloses a compound as shown in a formula I. The compound can be used for catalyzing a hydrosilicification reaction of allene or a hydroformylation reaction of terminal olefin, and has one or more advantages as follows: the operation is simple and convenient; the catalytic activity is high; the enantioselectivity of the product is high.

Description

technical field [0001] The invention relates to a spirobis-dihydrobenzosilrole phosphonite monoester compound, its preparation and application. Background technique [0002] As early as more than 150 years ago, the asymmetry of life in the universe and nature, that is, chirality, has been known. Although the enantiomers of chiral compounds are very similar in structure, many enantiomers of chiral compounds show different characteristics to living organisms. For example, they may have different tastes or odors, and even individual enantiomers may exhibit very different physiological activities or toxicity. As the most efficient means to obtain optically pure compounds, asymmetric catalytic reactions are also the most challenging. Finding economical, efficient and environmentally friendly asymmetric synthesis reactions has become the goal pursued by chemists. [0003] The core of asymmetric catalytic reactions is to develop chiral ligands or catalysts that are highly effici...

Claims

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Application Information

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IPC IPC(8): C07F9/6596B01J31/02C07C45/50C07C47/02C07C47/228C07C49/185
Inventor 王鹏王金平刘涛
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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