New enol acetates (II)

文档序号:310432 发布日期:2021-11-26 浏览:38次 中文

阅读说明:本技术 新的烯醇乙酸酯(ii) (New enol acetates (II) ) 是由 维尔纳·邦拉蒂 马克-安德烈·米勒 贝蒂娜·乌斯特伯格 弗洛里安·齐格勒 于 2020-04-03 设计创作,主要内容包括:本发明涉及式(I)的新的特定烯醇乙酸酯,并且涉及制备其的方法,所述方法通过相应二氢视黄醛类似物的酰化进行。在式(I)中,R为-COR’,其中R’为C-(1)-C-(16)烷基。(The invention relates to novel specific enol acetates of formula (I) and to a process for preparing them by acylation of the corresponding dihydroretinal analogues. In formula (I), R is-COR ', wherein R' is C 1 ‑C 16 An alkyl group.)

1. A compound of formula (I):

wherein the content of the first and second substances,

r is-COR',

wherein R' is C1-C16Alkyl (especially C)1Alkyl radical, C2Alkyl and C15Alkyl groups).

2. The compound according to claim 1, having formula (Ia):

wherein the content of the first and second substances,

r is-COR',

wherein R' is C1-C16Alkyl (preferably C)1Alkyl radical, C2-alkyl or C15-an alkyl group).

3. The compound of claim 1, having formula (Ib):

wherein

R is-COR',

wherein R' is C1-C16Alkyl (preferably C)1Alkyl radical, C2-alkyl or C15-an alkyl group).

4. A process for the preparation of a compound of formula (I) according to claim 1,

wherein the content of the first and second substances,

r is-COR',

wherein R' is C1-C16Alkyl (preferably C)1Alkyl radical, C2-alkyl or C15-an alkyl group),

the method is carried out by acetylation of a compound of formula (II),

by using at least one acetylating agent of formula (III):

wherein the content of the first and second substances,

r is-COR' or

Wherein R' is C1-C16Alkyl (preferably C)1Alkyl radical, C2-alkyl or C15-alkyl), and

r' is C1-C16Alkyl (preferably C)1Alkyl radical, C2-alkyl or C15-an alkyl group).

5. The process according to claim 4, wherein the process is carried out in the presence of at least one transition metal catalyst.

6. A process according to claim 4 or claim 5, wherein the amount of catalyst is from 0.001 molar equivalent up to 0.01 molar equivalent (relative to the compound of formula (II)).

7. The process according to any of the preceding claims 4-6, wherein the process is carried out in the presence of at least one organic acid.

8. The process according to any one of the preceding claims 4-6, wherein the process is carried out in the presence of at least one base.

9. The process according to claim 7 or claim 8, wherein the amount of acid or base is from 0.005 molar equivalents up to 0.1 molar equivalents (relative to the compound of formula (II)).

10. The process according to any one of the preceding claims 4-9, wherein the process is carried out in an inert solvent.

11. The process according to any one of the preceding claims 4-9, wherein the process is carried out in the absence of any solvent.

12. The process according to any of the preceding claims 4-11, wherein the process is carried out at a temperature of 0-100 ℃ (preferably 5-90 ℃).

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