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Synthetic method of spirocyclic compound containing 1-indanone skeleton

A synthesis method and compound technology, applied in the field of synthesis of spirocyclic compounds containing 1-indanone skeleton, to achieve the effects of easy to obtain raw materials, cheap raw materials, and simple reaction operations

Active Publication Date: 2018-05-18
SHAANXI NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the application of this strategy to the synthesis of 1-indanone skeleton spirocyclic compounds has not been reported in the literature

Method used

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  • Synthetic method of spirocyclic compound containing 1-indanone skeleton
  • Synthetic method of spirocyclic compound containing 1-indanone skeleton
  • Synthetic method of spirocyclic compound containing 1-indanone skeleton

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Add 13.6mg (0.1mmol) o-toluic acid, 25μL (0.25mmol) 1-penten-3-one, 3.1mg (0.0050mmol) p-cymene dichloride ruthenium dimerization to a 10mL pressure-resistant reaction tube solid, 13.0mg (0.0750mmol) anhydrous manganese acetate, 0.6mL acetonitrile, stirred and reacted at 150°C for 20 hours under the protection of argon, cooled to room temperature after the reaction, and filtered by column chromatography silica gel column to remove the catalyst and some insoluble salts , separated by thin-layer chromatography to obtain a spirocyclic compound containing a 1-indanone skeleton with the following structural formula:

[0019]

[0020] Its yield is 62%, and the structural characterization data are as follows:

[0021] 1 H NMR (400MHz, CDCl 3 ): δ[ppm]=7.41(t, J=7.5Hz, 1H), 7.24(d, J=8.4Hz, 1H), 7.08(d, J=7.4Hz, 1H), 3.65(d, J=17.0 Hz,1H),2.88–2.76(m,2H),2.58(s,3H),2.42–2.25(m,4H),2.11–2.02(m,1H),1.79(s,3H),1.13(t, J=7.6Hz, 3H).

[0022] 13 C NMR (100MHz, CDCl 3 ): δ[...

Embodiment 2

[0025] The o-toluic acid used in Example 1 is replaced with an equimolar amount of o-ethylbenzoic acid, and other steps are the same as in Example 1 to obtain the following structural formula containing 1-indanone skeleton spirocyclic compound:

[0026]

[0027] Its yield is 58%, and the structural characterization data are as follows:

[0028] 1 H NMR (400MHz, CDCl 3 ): δ[ppm]=7.45(t, J=7.5Hz, 1H), 7.25(d, J=6.7Hz, 1H), 7.13(d, J=7.5Hz, 1H), 3.66(d, J=16.9 Hz,1H),3.03(qd,J=7.3,2.3Hz,2H),2.83(d,J=17.0Hz,2H),2.41–2.25(m,4H),2.12–2.01(m,1H),1.80 (s, 3H), 1.19 (t, J = 7.5Hz, 3H), 1.13 (t, J = 7.6Hz, 3H).

[0029] 13 C NMR (100MHz, CDCl 3 ): δ[ppm]=204.9, 197.1, 161.3, 153.9, 146.0, 134.4, 132.0, 129.3, 127.6, 123.7, 59.6, 37.6, 31.5, 28.4, 26.7, 24.8, 14.7, 11.7, 10.8.

[0030] HRMS(ESI)m / z:C 19 h 22 o 2 ,[M+Na] + , The theoretical value is 305.1517; the measured value is 305.1506.

Embodiment 3

[0032] The o-toluic acid used in Example 1 is replaced with an equimolar amount of 2,3-dimethylbenzoic acid, and the other steps are the same as in Example 1 to obtain a 1-indanone skeleton-containing spiro compound with the following structural formula :

[0033]

[0034] Its yield is 61%, and the structural characterization data are as follows:

[0035] 1 H NMR (400MHz, CDCl 3 ): δ[ppm]=7.32(d, J=7.7Hz, 1H), 7.15(d, J=7.7Hz, 1H), 3.57(d, J=16.8Hz, 1H), 2.85–2.77(m, 2H ),2.55(s,3H),2.40–2.31(m,4H),2.28(s,3H),2.09–2.01(m,1H),1.80(s,3H),1.13(t,J=7.6Hz, 3H).

[0036] 13 C NMR (100MHz, CDCl 3 ): δ[ppm]=205.6, 197.2, 161.1, 151.5, 137.8, 136.4, 136.0, 132.5, 129.2, 123.1, 59.9, 36.9, 31.4, 28.4, 26.7, 18.9, 13.6, 11.6, 10.7.

[0037] HRMS(ESI)m / z:C 19 h 22 o 2 ,[M+Na] + , The theoretical value is 305.1517; the measured value is 305.1519.

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Abstract

The invention discloses a synthetic method of a spirocyclic compound containing 1-indanone skeleton. The method comprises the following steps: taking aromatic carboxylic acid and alpha, beta-unsaturated ketone as raw materials, taking any of p-cymene ruthenium chloride dimer, pentamethylcyclopetadienyl rhodium chloride dimmer, tris(acetonitrile)(pentamethylcyclopentadienyl)rhodium bis(hexafluoroantimonate) as a catalyst, taking any of anhydrous manganese acetate, manganese acetate tetrahydrate, anhydrous zinc acetate and zinc acetate as an additive, and thus synthesizing the spirocyclic compound containing 1-indanone skeleton by adopting a one-step method. The reaction comprises four steps such as conjugate addition reaction of aromatic carboxylic acid ortho-position C-H bond and alpha, beta-unsaturated ketone, intramolecular dehydration, Michael addition with second molecular alpha,beta-unsaturated ketone and intramolecular aldol condensation. The synthetic method has the characteristics that the raw materials are low in price and easy to obtain, the efficiency is high, the atom utilization rate is high, the reaction operation is simple and four new C-C bonds are constructed by adopting the one-step method.

Description

technical field [0001] The invention belongs to the technical field of synthesis of spirocycles, and in particular relates to a method for synthesizing spirocyclic compounds containing 1-indanone skeletons. Background technique [0002] Spiral ring skeletons have unique structural characteristics and are widely used in biomolecules and natural product synthesis (Chem.Soc.Rev.2012,41,1060-1074; Eur.J.Org.Chem.2012,1935-1944; Org . Chem. Front. 2015, 2849-2858; ACS Catal. 2013, 3, 540-553). Many compounds with spirocyclic skeletons have shown good biological activities in clinical applications, such as antibacterial, antipsychotic, antitumor, etc. (J.Med.Chem.1996,39,4044-4057; Med.Chem.Lett.2007, 17, 266-271; Synthesis-Stuttgart. 2013, 45, 1909-1930; J. Med. Chem. 2009, 52, 6936-6940). As multifunctional intermediates, spirocycles are also used in the synthesis of ligands and catalysts. [0003] Traditionally, the construction of the spiro ring is through a multi-step meth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/00C07C45/45C07C49/675C07C49/697C07C49/755C07B41/06
CPCC07B41/06C07C45/00C07C45/455C07C49/675C07C49/697C07C49/755
Inventor 石先莹王嘉妮陈思琪张子楠韩文静
Owner SHAANXI NORMAL UNIV
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