Synthetic method of highly-activity chiral acetylenic alcohol (S,E)-1,9-diene-4,6-diacetyl-3-octadecyl alcohol

A synthesis method, technology of stearyl alcohol, applied in the fields of compounds of group 4/14 elements of the periodic table, organic chemical methods, chemical instruments and methods, etc., can solve the problems of limitations and disadvantages of the three-seventh distribution of the screen, and avoid Effects of racemization, increased yield, and mild reaction conditions

Inactive Publication Date: 2018-08-24
HENAN AGRICULTURAL UNIVERSITY
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Problems solved by technology

[0003] Up to now, no one has reported the synthesis method of (S,E)-1,9-diene-4,6-diyne-3-octadecyl alcohol, and the distribution of Panax notoginseng is relatively limited, which is not conducive to (S ,E)-1,9-diene-4,6-diyne-3-octadecyl alcohol extraction and production

Method used

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  • Synthetic method of highly-activity chiral acetylenic alcohol (S,E)-1,9-diene-4,6-diacetyl-3-octadecyl alcohol
  • Synthetic method of highly-activity chiral acetylenic alcohol (S,E)-1,9-diene-4,6-diacetyl-3-octadecyl alcohol
  • Synthetic method of highly-activity chiral acetylenic alcohol (S,E)-1,9-diene-4,6-diacetyl-3-octadecyl alcohol

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Embodiment 1

[0026] The synthesis method of the highly active chiral acetylenic alcohol (S,E)-1,9-diene-4,6-diyne-3-octadecyl alcohol in this example, the steps are as follows:

[0027] (1) Synthesis of 2-undecyne-1-alcohol: In a 250ml three-necked flask equipped with a magnetic stirrer under inert gas protection, add propynyl alcohol (4.7ml, 80mmol) and hexamethylphosphoryl in sequence Triamine (42ml, 240mmol) and tetrahydrofuran (40ml) were cooled to -78°C, and n-butyllithium (64ml, 160mmol) was added slowly. Stir at -20°C for 3h, then slowly add 1-bromooctane (7.7248g, 40mmol) at -20°C. After the reaction system continued to stir for 50 min, it was heated to room temperature and stirred for 24 h, and the reaction progress was monitored at any time by thin-layer chromatography. After the reaction, the system was quenched with water, the aqueous phase was extracted with ether, the organic phases were combined, washed with saturated saline solution, anhydrous Na 2 SO 4 dry. After preci...

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Abstract

The invention discloses a synthetic method of highly-activity chiral acetylenic alcohol (S,E)-1,9-diene-4,6-diacetyl-3-octadecyl alcohol. The synthetic method disclosed by the invention comprises thefollowing steps: bromooctane is taken as a starting raw material and is reacted in a reasonable proportion to synthesize required alkynol; and the efficient synthesis of active molecule (S,E)-1,9-diene-4,6-diyne-3-octadecanol is realized through reduction, bromination, coupling reactions, desilication and docking with a chiral molecule. According to the method, the yield in the reaction process ishigh, a synthetic route is simple, the raw material is simple and easy to obtain, the synthetic cost is low, reaction conditions are mild, the separation and purification operations are simple, and ahigh-purity target compound can be directly obtained; a chiral center is introduced in the last step, so that the possibility of racemization of the substance in the reaction is avoided; and in addition, the synthesized active molecule (S,E)-1,9-diene-4,6-diyne-3-octadecanol has a wide application prospect.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing highly active chiral acetylenic alcohol (S, E)-1,9-diene-4,6-diyne-3-octadecyl alcohol. Background technique [0002] Pingbian notoginseng (panax stipuleanatus), also known as wild notoginseng and soil notoginseng, is a perennial herb distributed in southeastern Yunnan (Maguan, Malipo, Pingbian) valleys at an altitude of 1100-1700 meters It is relatively rare in humid forests and in Lao Cai in northern Vietnam. "Supplements to Materia Medica" records that the root of Pingbian Sanqi is often used as medicine. It tastes slightly bitter, sweet, and warm in nature. Because of this special activity, the active substance extracted from Pingbian Sanqi has been widely concerned by the pharmaceutical community. In 2011, the research team of Vietnam Academy of Science and Technology, Chungnam National University of South Korea and Jeju National Univer...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C29/34C07C33/048A01P3/00
CPCC07B2200/07C07C17/16C07C29/17C07C29/34C07F7/083C07C33/048C07C19/075C07C33/03C07C33/042
Inventor 那日松刘佳李洪连丁胜利张猛陈琳琳冯家阳王金玲卢世超
Owner HENAN AGRICULTURAL UNIVERSITY
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