Unlock instant, AI-driven research and patent intelligence for your innovation.

Novel cyclotriveratrol analogs and derivatives thereof, preparation methods and applications

A technology of analogues and derivatives, applied in the field of preparation of novel cyclotriveratrol analogues and their derivatives, achieving the effects of easy modification, high yield and simple synthesis process

Active Publication Date: 2021-09-28
NANJING UNIV
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, water-soluble macrocycles play a very important role in living systems, but there are few reports on water-soluble triveratrol analogs and their host-guest properties (D.Xia, Y.Li, K.Jie ,B.Shi,Y.Yao,Org Lett 2016,18,2910-2913; F.Yang,Q.Chen,Q.Y.Cheng,C.G.Yan,B.H.Han,J Org Chem 2012,77,971-976;L.-J. Feng, H. Li, Q. Chen, B.-H. Han, RSC Advances 2013, 3; M. L. Dumartin, C. Givelet, P. Meyrand, B. Bibal, I. Gosse, Org Biomol Chem 2009, 7, 2725 -2728.), Synthesizing water-soluble cyclotriveratrol analogs and studying their host-guest properties have always been a difficult problem

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Novel cyclotriveratrol analogs and derivatives thereof, preparation methods and applications
  • Novel cyclotriveratrol analogs and derivatives thereof, preparation methods and applications
  • Novel cyclotriveratrol analogs and derivatives thereof, preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Novel cyclotriveratrol analogue, said analogue is the ring trimer of 2,3-dimethylhydroquinone, its structural formula is

[0047]

[0048] Synthetic route such as figure 1 Shown, the preparation method of above-mentioned novel cyclotriveratrol analogue, described method comprises the following steps:

[0049] a. Add 2,3-dimethylhydroquinone and formaldehyde hydrate to acetic acid, then add 3 equivalents of hydrochloric acid, and stir the reaction at room temperature;

[0050] b. Filter the solution after the reaction in step a, and vacuum-dry the obtained solid to obtain the cyclotrimer of 2,3-dimethylhydroquinone.

[0051] In step a above, the molar ratio of 2,3-dimethylhydroquinone to formaldehyde hydrate is 1:1, and the reaction is stirred for 3 hours at room temperature, and the room temperature is 15°C-30°C.

Embodiment 2

[0053] The derivatives of the novel cyclotriveratrol analogues, the derivatives are the ring trimers of methylene bridged 2,3-dimethylhydroquinone, and its structural formula is

[0054] Cyclic trimer of 2,3-dimethylhydroquinone bridged with a water-soluble methylene group, its structural formula is

[0055]

[0056] Synthetic route such as figure 1 As shown, the preparation method of the derivatives of the above-mentioned novel cyclotriveratrol analogues is characterized in that the method comprises the following steps:

[0057] c. Add the product obtained in step b and potassium carbonate to N,N-dimethylformamide, then add 1 equivalent of bromochloromethane, and heat to 70°C under the protection of an inert gas to react with stirring;

[0058] d. Filtrating the solution obtained from the reaction in step c, removing the insoluble solids, rotating the filtrate to remove the organic solvent, and obtaining a cyclotrimer of methylene bridged 2,3-dimethylhydroquinone;

[0...

Embodiment 3

[0064] The derivative of the novel cyclotriveratrol analogue, the derivative is a ring trimer of 2,3-dimethylhydroquinone connected by a silicon group, and its structural formula is

[0065]

[0066] Synthetic route such as figure 1 Shown, the preparation method of the derivative of novel ring triveratrol analog described above, described method comprises the following steps:

[0067] h. Dissolving the product obtained in step b in pyridine, adding 3 equivalents of dichlorodimethylsilane, and heating the reaction mixture at 70-100°C for 3-6h;

[0068] i. Cool the solution after the reaction in step h to room temperature, distill off the organic solvent under reduced pressure, add methanol, and filter the resulting filter cake to be a cyclotrimer of silicon-linked 2,3-dimethylhydroquinone.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses novel cyclotriveratrol analogs and their derivatives, preparation methods and applications, and provides the following five compounds: CTX, CTX[CH 2 ], CTX[SiMe 2 ], CTX[P(O)Ph], WCTX[CH 2 ]. Compared with the prior art, the present invention has the following advantages: (1) the novel cyclotriveratrol analog of the present invention is the first reported cyclotriveratrol with four substituents on each aromatic ring so far The analog overcomes the defect of not obtaining this analog in the prior art due to steric hindrance; (2) the synthesis process of the novel analog is simple, the yield is high, there are no other by-products, no purification is required, and it is easy to modify (3) the present invention can rapidly synthesize water-soluble WCTX[CH 2 ], for CTX[CH 2 ] was directly obtained by oxidation on the upper edge without column chromatography purification.

Description

technical field [0001] The invention belongs to the technical field of supramolecular chemistry, and relates to a novel macrocyclic main compound and its synthesis and application, specifically novel cyclotriveratrol analogs and derivatives thereof, preparation methods and applications. Background technique [0002] Supramolecular chemistry is a science that studies the assembly of two or more molecules into complex, organized structures with specific topological structures and functions through intermolecular forces. Supramolecular chemistry emerged from the 1960s to the 1970s, and has experienced great progress in just a few decades. Its main concepts and research methods have been widely used to study and solve various problems. The development of supramolecular chemistry is inseparable from the continuous discovery and successful synthesis of various macrocyclic host molecules, including several classic macrocyclic host compounds such as crown ethers, cyclodextrins, cali...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07C39/17C07D493/18C07F7/18C07F9/6574C07C37/07G01N24/08
CPCC07C39/17C07D493/18C07F7/1804C07F7/188C07F9/657181C07C2603/40G01N24/08
Inventor 林晨强琚莉王乐勇焦建敏孙宝宝丁逸涵
Owner NANJING UNIV