Extracyclic Z, E-diene-containing cis-tetrahydrobenzofuran compound and synthesis method thereof

A synthesis method and benzofuran technology are applied in the field of cis-tetrahydrobenzofuran structural compounds, can solve problems such as the method not being reported, and achieve the effects of reasonable reaction path, mild reaction conditions and high efficiency

Active Publication Date: 2020-03-10
HENAN NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, the method of cis-tetrahydrobenzofuran structu

Method used

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  • Extracyclic Z, E-diene-containing cis-tetrahydrobenzofuran compound and synthesis method thereof
  • Extracyclic Z, E-diene-containing cis-tetrahydrobenzofuran compound and synthesis method thereof
  • Extracyclic Z, E-diene-containing cis-tetrahydrobenzofuran compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0040] Example 1:

[0041] The synthetic route of compound 3aa is as follows:

[0042]

[0043] The synthesis steps of compound 3aa are as follows:

[0044] The compound 1a (0.6mmol, 3.0eq), Cp*Rh(OAc) 2 -H 2 O (0.02mmol, 0.1eq), compound 2a (0.2mmol, 1.0eq), react at 60℃ until the material 2a disappears completely (about 9h) as monitored by TLC; spin dry the solvent, and separate by column chromatography (wash Removal agent: petroleum ether / ethyl acetate volume ratio 2:1) to obtain 55 mg of yellow solid 3aa, melting point 61-63°C, yield: 85%.

[0045] 1 H NMR(600MHz, CDCl 3 ): 7.32(t,J=7.5Hz,2H),7.24-7.20(m, 3H),7.09(dd,J=11.9,1.7Hz,1H),6.59(d,J=10.2Hz,1H),6.52 (d,J = 11.9Hz, 1H), 6.03 (d, J = 10.2Hz, 1H), 4.52-4.43(m, 2H), 3.68(s, 2H), 3.14-3.12(m, 1H), 2.59( dd, J = 16.4, 7.3 Hz, 1H), 2.50 (dd, J = 16.4, 6.1 Hz, 1H), 1.43 (s, 3H). 13 C NMR(100MHz, CDCl 3 ):197.1,171.8,150.8,149.5,138.9,137.4,129.1,128.8,126.7,118.8,79.6,70.9,46.0,40.2, 39.4,24.4.HRMS(ESI-TOF)m / z:[M+Na] + Calcd fo...

Example Embodiment

[0046] Example 2:

[0047]

[0048] use replace The reaction temperature was 60°C, and other experimental procedures and purification methods were carried out with reference to Example 1; within 9 hours, 62 mg of yellow solid 3ab was obtained, the melting point was 43-45°C, and the yield: 91%.

[0049] 1 H NMR(600MHz, CDCl 3 ): 7.32(t,J=7.5Hz,2H),7.24-7.20(m, 3H),7.07(dd,J=11.9,1.6Hz,1H),6.54(d,J=11.9Hz,1H),6.37 (d,J = 0.9Hz, 1H), 4.51 (d, J = 15.0Hz, 1H), 4.46 (d, J = 15.1Hz, 1H), 3.68 (s, 2H), 3.12-3.10 (m, 1H) , 1.79(s, 3H), 1.39(s, 3H). 13 CNMR(150MHz, CDCl 3 ):197.6,172.2,151.5,144.6,139.0,137.8,136.6,129.4,129.0,128.7,126.7,118.6,80.1,70.7,46.2,40.2,39.6,24.8,15.8.HRMS(ESI-TOF)m / z: [M+Na] + Calcd for Chemical Formula:C 21 H 22 NaO 4 + 361.1410, Found:361.1414.

Example Embodiment

[0050] Example 3:

[0051]

[0052] use instead Other experimental procedures and purification methods were carried out with reference to the steps in Example 1; within 9 hours, 70 mg of white solids were obtained, the melting point was 79-81°C, and the yield was 87%.

[0053] 1 H NMR(600MHz, CDCl 3 ): 7.33 (t, J = 7.6 Hz, 2H), 7.25-7.19 (m, 3H), 7.09 (dd, J = 11.9, 1.8 Hz, 1H), 7.03 (s, 1H), 6.46 (d, J = 11.9Hz, 1H),4.58-4.41(m,2H),3.74-3.63(m,2H),3.15-3.13(m,J=6.0Hz,1H), 2.77(dd,J=16.3,7.1Hz,1H ), 2.63(dd,J=16.3,5.8Hz,1H),1.46(s, 3H). 13 C NMR(150MHz, CDCl 3 ): 188.9,172.1,150.0,149.3,138.7,137.0,130.3,129.2,128.8,126.8,125.0,119.3,82.2,71.1,46.1,40.1, 39.3,24.2.HRMS(ESI-TOF)m / z:(M +Na] + Calcd for C 20 H 19 NaO 4 + 425.0359, Found: 425.0354.

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Abstract

The invention provides an extracyclic Z, E-diene unit -containing cis-tetrahydrobenzofuran compound and a preparation method thereof, and belongs to the field of organic chemistry. According to the present invention, the specific structure of the compound is obtained by the method that the synthesis of the compound can be completed in one step in the presence of a rhodium catalyst so as to highlyselectively obtain the extracyclic Z, E-diene unit -containing cis-tetrahydrobenzofuran compound. The method has the advantages of mild reaction conditions, reasonable reaction path, simple post-treatment, and high stereoselectivity and regioselectivity of the reaction product, and the extracyclic Z, E-diene unit -containing cis-tetrahydrobenzofuran compound shows good activity in inhibition of NF-kappa B signaling pathway.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to a cis-tetrahydrobenzofuran structure compound containing an exocyclic (Z, E)-diene unit, a preparation method and an application thereof. Background technique [0002] The cis-tetrahydrobenzofuran structure compound is a very important class of structures that widely exist in natural products and active compounds such as Sorbicillactone A (Angew. Chem., Int. Ed. 2008, 47, 1935-1937) , (+)-Paeonilactone B (Tetrahedron 2005, 61, 7252-7265). The backbone structure III containing an extracyclic double bond structure has also been shown to be an inhibitor of NF-κB signaling pathway (ACS Med. Chem. Lett. 2012, 3, 459-464). [0003] [0004] At present, the method of cis-tetrahydrobenzofuran structure compound containing exocyclic diene unit is still not reported. Therefore, the development of high-efficiency synthesis of such compounds can obtain a kind of skeleton stru...

Claims

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Application Information

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IPC IPC(8): C07D307/79C07D307/77A61P35/00
CPCC07D307/79C07D307/77A61P35/00C07B2200/07
Inventor 刘丙贤王娟娟李鹏飞张雅雯戴雨倩高紫莹王辰喆
Owner HENAN NORMAL UNIV
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