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Synthesis method of sclareleaf sclareleaf diol compound

A technology of sclareol and a synthesis method, which is applied in the field of iridium-catalyzed hydrogenation synthesis of sclarediols, can solve the problems of low atom economy, troublesome post-processing, high price and the like, and achieves less catalyst consumption , reduce the reaction cost, the effect of simple preparation

Pending Publication Date: 2022-05-20
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But neither LiAlH 4 or NaBH 4 Compared with direct hydrogen reduction, the price is expensive, and the post-processing is troublesome, and the atom economy is not high

Method used

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  • Synthesis method of sclareleaf sclareleaf diol compound
  • Synthesis method of sclareleaf sclareleaf diol compound
  • Synthesis method of sclareleaf sclareleaf diol compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] The structural formula of L-1 is as follows:

[0047]

[0048] In the glove box, 1.3 mg [Ir(COD)Cl] 2 Dissolve 2.1mg of ligand L-1 in 2mL of methanol, stir at room temperature for 30 minutes, add it to 10g of sclareolactone, add 44.8mg of potassium tert-butoxide, 30mL of methanol, and place it in an autoclave In the process, the hydrogen gas was replaced 3 times, and then the hydrogen gas was introduced to 20 bar, and the reaction was carried out at 25°C for 12 hours, and the hydrogen gas was slowly released. After the solvent was removed, water was added, and then extracted with ethyl acetate, dried over sodium sulfate, and a white solid was obtained after the solvent was removed. Column chromatography, and then determined by NMR, obtained 4.3 g of sclareolactone and 5.2 g of sclareolide. Then the analytical method was established by GC analysis. The NMR data are as follows:

[0049] 1 H NMR (400MHz, CDCl 3 ( m,6H). 13 C NMR (400MHz, CDCl 3 )δ73.0, 64.0, 59.3,...

Embodiment 2

[0051] The structural formula of L-2 is as follows:

[0052]

[0053] The ligand L-1 in Example 1 is replaced by the ligand L-2 and the rest is the same as in Example 1. GC monitoring conversion was 70%.

Embodiment 3

[0055] The alkali additive potassium tert-butyl in embodiment 1 is replaced with lithium tert-butoxide, and all the other are the same as embodiment 1. GC monitoring conversion was 80%.

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Abstract

The invention provides a synthesis method of a sclarediol compound, which comprises the following steps: by taking sclareolide as a raw material, carrying out hydrogenation reaction under the action of a catalyst system consisting of metal iridium and ferrocene P, N, N skeleton structure ligands, so as to obtain sclarediol at high yield. The catalytic reaction needs to be carried out at room temperature to 100 DEG C by taking isopropanol, methylbenzene and the like as solvents under the action of alkali additives such as potassium tert-butoxide. The method has the advantages of high reaction activity, mild reaction conditions, cheap and easily available initial raw materials, cleanness, environmental protection and very high industrial application value.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to an iridium-catalyzed hydrogenation synthesis method of a sclarediol compound. Background technique [0002] Ambergris is a kind of spice with elegant animal fragrance, and musk, civet, and sea lily are also known as the four major animal spices. Ambergris not only has a long-lasting fragrance, but also has good harmony, and it plays a very important role in high-end luxury perfumes [(a) Wang Yao, Tao Feiyan, Zhou Zhigang, Luo Cheng, Xu Heng, Synthetic Chemistry, 2018, 26(1) 55- 65; (b) Wang Wenjun, Chen Sha, Dai Qianyuan, Organic Chemistry, 2001, 21(3)167-172]. [0003] Ambergris comes from the metabolites of sperm whales. As sperm whales are on the verge of extinction, natural ambergris is less and less, so ambergris substitutes came into being. At present, the most characteristic of ambergris is ambrox [(c) Lu Jiaqing, Pan Xianhua, Ou Wenhua, Fragrance, Fragrance ...

Claims

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Application Information

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IPC IPC(8): C07C29/00C07C29/149C07C35/36B01J31/24B01J31/22
CPCC07C29/00C07C29/149B01J31/2404B01J31/2239C07B2200/07C07C2602/28B01J2531/842B01J2531/827C07C35/36Y02P20/584
Inventor 胡向平陈修帅
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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