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Spiro bis(dihydrobenzosilole) phosphoric acid compound as well as synthesis method and application of spiro bis(dihydrobenzosilole) phosphoric acid compound

A technology for spirobisdihydrobenzothiazole phosphoric acid and compounds, which is applied in the directions of organic chemistry methods, carbon-based compound preparation, chemical instruments and methods, etc. Mild, readily available effects

Active Publication Date: 2021-12-03
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 spirobidihydrobenzene in order to overcome the single defect of the existing chiral catalyst phosphoric acid ligand Thiazole phosphoric acid compound, its preparation method and application

Method used

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  • Spiro bis(dihydrobenzosilole) phosphoric acid compound as well as synthesis method and application of spiro bis(dihydrobenzosilole) phosphoric acid compound
  • Spiro bis(dihydrobenzosilole) phosphoric acid compound as well as synthesis method and application of spiro bis(dihydrobenzosilole) phosphoric acid compound
  • Spiro bis(dihydrobenzosilole) phosphoric acid compound as well as synthesis method and application of spiro bis(dihydrobenzosilole) phosphoric acid compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 2

[0291] Embodiment 2: I-2

[0292]

[0293] White solid, 78% yield, [a] D 24 =+101.87 (c=0.90, CHCl 3 ); 1H NMR (400MHz, chloroform-d) δ7.34(t, J=7.6Hz, 2H), 7.16(d, J=7.6Hz, 2H), 7.05(d, J=8.0Hz, 2H), 3.54(p ,J=7.6Hz,2H),1.75(dd,J=14.0,8.4Hz,2H),1.45(d,J=6.8Hz,6H),1.07(d,J=14.0Hz,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 PNMR (162MHz, chloroform-d) δ-7.98.; HRMS (ESI-TOF) m / z calculated value C 18 h 19 o 4 SiP[M+H] + :359.0863, measured value: 359.0863.

Embodiment 3

[0294] Embodiment 3: I-3

[0295]

[0296] White solid, equivalent conversion, [a] D 24 =-185.67 (c=0.90, CHCl 3 ); 1 H NMR (400MHz, chloroform-d) δ7.33 (s, 2H), 7.14 (d, J = 32.4Hz, 4H), 3.05–3.28 (m, 4H), 1.41–1.33 (m, 4H); 13 C NMR (101MHz, chloroform-d) δ156.70, 154.06, 132.67, 128.63, 123.36, 118.63, 31.69, 14.58; 31 P NMR (162MHz, chloroform-d) δ-7.23; HRMS (ESI-TOF) m / z calculated value C 16 h 16 o 4 SiP[M+H] + :331.0553, measured value: 331.0550.

Embodiment 4

[0297] Embodiment 4: I-4

[0298]

[0299] White solid, equivalent conversion, [a] D 24 =+185.67 (c=0.90, CHCl 3 ); 1 H NMR (400MHz, chloroform-d) δ7.33 (s, 2H), 7.14 (d, J = 32.4Hz, 4H), 3.05–3.28 (m, 4H), 1.41–1.33 (m, 4H); 13 C NMR (101MHz, chloroform-d) δ156.70, 154.06, 132.67, 128.63, 123.36, 118.63, 31.69, 14.58; 31 P NMR (162MHz, chloroform-d) δ-7.23; HRMS (ESI-TOF) m / z calculated value C 16 h 16 o 4 SiP[M+H] + :331.0553, measured value: 331.0550.

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Abstract

The invention discloses a spiro bis(dihydrobenzosilole) phosphoric acid compound as well as a synthesis method and application of the spiro bis(dihydrobenzosilole) phosphoric acid compound. The invention provides a method for efficiently constructing a spiro bis(dihydrobenzosilole) phosphoric acid compound as shown in a formula I by using a spiro bis(dihydrobenzosilole) diphenol compound. The method has the characteristics of simplicity and convenience in operation, easiness in obtaining raw materials, mild reaction conditions, high yield, convenience in purification and the like. The spiro bis(dihydrobenzosilole) phosphoric acid compound as shown in the formula I provided by the invention can be directly used as a chiral organic catalyst, or can be used for generating metal complexes with metal salts from the third group to the thirteenth group or can be mixed in situ for use, and is used for catalyzing an asymmetric organic synthesis reaction.

Description

technical field [0001] The invention relates to a spirobis-dihydrobenzothialophosphate compound, a synthesis method and an application thereof. Background technique [0002] Chirality is one of the fundamental properties of nature. Chiral compounds widely exist in natural products, drug molecules and biomacromolecules. In the pharmaceutical industry, chirality is also directly related to the pharmacological action, clinical effect, side effects, drug effect and drug effect time of the drug. Before chiral drugs were recognized by people, some European doctors gave pregnant women racemic (thalidomide) as an analgesic or cough medicine. After taking it, many pregnant women gave birth to congenital deformities. Later studies found that the R-configuration of thalidomide has a sedative effect, but the S-enantiomer has a strong teratogenic effect on embryos. Because of this, the development of methods for constructing optically homochiral compounds is crucial to the technologic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6596B01J31/02C07B53/00C07B61/00C07C45/68C07C49/657C07C221/00C07C225/18C07D213/40C07D217/18C07D401/10
CPCC07F9/6596C07B53/00C07B61/02C07D213/40C07D401/10C07D217/18C07C45/68C07C221/00B01J31/0274B01J31/0275C07B2200/07C07C2601/14B01J2231/4205B01J35/39C07C49/657C07C225/18
Inventor 王鹏张雨兰
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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