• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

通过还原β-烯胺酮合成顺式和反式 3-氨基环己醇。

Synthesis of cis- and trans-3-aminocyclohexanols by reduction of β-enaminoketones.

机构信息

Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, Cuernavaca, Mor., CP 62209, Mexico.

出版信息

Molecules. 2011 Dec 27;17(1):151-62. doi: 10.3390/molecules17010151.

DOI:10.3390/molecules17010151
PMID:22202804
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6268485/
Abstract

We describe a protocol developed for the preparation of β-enaminoketones derived from 1,3-cyclohexanediones, and their subsequent reduction by sodium in THF-isopropyl alcohol to afford cis- and trans-3-aminocyclohexanols.

摘要

我们描述了一种从 1,3-环己二酮制备β-烯胺酮的方法,以及它们随后在四氢呋喃-异丙醇中被钠还原为顺式和反式-3-氨基环己醇。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9868/6268485/ae4f86718959/molecules-17-00151-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9868/6268485/0b5dd80b694d/molecules-17-00151-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9868/6268485/4b98eaa5685f/molecules-17-00151-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9868/6268485/9c670f79b731/molecules-17-00151-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9868/6268485/28f18d649e22/molecules-17-00151-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9868/6268485/2a3ff2f42719/molecules-17-00151-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9868/6268485/36f66fe4a52a/molecules-17-00151-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9868/6268485/5e04b5895a29/molecules-17-00151-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9868/6268485/377cae7612da/molecules-17-00151-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9868/6268485/ae4f86718959/molecules-17-00151-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9868/6268485/0b5dd80b694d/molecules-17-00151-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9868/6268485/4b98eaa5685f/molecules-17-00151-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9868/6268485/9c670f79b731/molecules-17-00151-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9868/6268485/28f18d649e22/molecules-17-00151-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9868/6268485/2a3ff2f42719/molecules-17-00151-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9868/6268485/36f66fe4a52a/molecules-17-00151-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9868/6268485/5e04b5895a29/molecules-17-00151-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9868/6268485/377cae7612da/molecules-17-00151-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/9868/6268485/ae4f86718959/molecules-17-00151-g007.jpg

相似文献

1
Synthesis of cis- and trans-3-aminocyclohexanols by reduction of β-enaminoketones.通过还原β-烯胺酮合成顺式和反式 3-氨基环己醇。
Molecules. 2011 Dec 27;17(1):151-62. doi: 10.3390/molecules17010151.
2
Resolution of racemic 2-aminocyclohexanol derivatives and their application as ligands in asymmetric catalysis.外消旋2-氨基环己醇衍生物的拆分及其作为配体在不对称催化中的应用。
J Org Chem. 2006 Mar 17;71(6):2320-31. doi: 10.1021/jo052433w.
3
Domino synthesis of bridged bicyclic tetrahydro-1,2-oxazines: access to stereodefined 4-aminocyclohexanols.桥连双环四氢-1,2-恶嗪的多米诺合成:立体定向4-氨基环己醇的合成方法
Org Lett. 2009 Aug 20;11(16):3694-7. doi: 10.1021/ol901454y.
4
Effective chiral pool synthesis of both enantiomers of the TRPML inhibitor trans-ML-SI3.高效手性池合成 TRPML 抑制剂反式-ML-SI3 的两种对映异构体。
Arch Pharm (Weinheim). 2022 Feb;355(2):e2100362. doi: 10.1002/ardp.202100362. Epub 2021 Nov 5.
5
How a diversity-oriented approach has inspired a new hypothesis for the gabosine biosynthetic pathway. A new synthesis of (+)-gabosine C.一种面向多样性的方法如何为 gabosine 生物合成途径激发了一个新的假设。(+)-gabosine C 的新合成。
Org Biomol Chem. 2013 Oct 14;11(38):6562-8. doi: 10.1039/c3ob41183d. Epub 2013 Aug 28.
6
Stereoselective prins cyclizations of delta, epsilon-unsaturated ketones to cis-3-chlorocyclohexanols with TiCl(4).
Angew Chem Int Ed Engl. 2002 Feb 1;41(3):491-3. doi: 10.1002/1521-3773(20020201)41:3<491::aid-anie491>3.0.co;2-3.
7
A short synthesis of (+)-cyclophellitol.(+)-环落叶松醇的简短合成
J Org Chem. 2005 Nov 25;70(24):10139-42. doi: 10.1021/jo051645q.
8
Diastereoselective synthesis of vicinal cis-dihydroxyheterospirocycles by one-pot epoxidation/spirocyclization of C(3)-functionalized cyclohex-2-en-1-ols.通过 C(3)-官能化环己-2-烯-1-醇的一锅法环氧化/螺环化反应,立体选择性合成顺式邻位二羟基杂螺环化合物。
Org Biomol Chem. 2013 May 28;11(20):3393-9. doi: 10.1039/c3ob27352k.
9
Ammonium-directed dihydroxylation: metal-free synthesis of the diastereoisomers of 3-aminocyclohexane-1,2-diol.铵导向的二羟基化反应:3-氨基环己烷-1,2-二醇非对映异构体的无金属合成
Org Biomol Chem. 2008 Oct 21;6(20):3762-70. doi: 10.1039/b808812h. Epub 2008 Aug 20.
10
Biocatalytic reduction of racemic 2-arenoxycycloalkanones by yeasts P. glucozyma and C. glabrata: one way of achieving chiral 2-arenoxycycloalcohols.酵母 P. glucozyma 和 C. glabrata 对消旋 2-芳氧基环烷酮的生物催化还原:获得手性 2-芳氧基环醇的一种方法。
Appl Microbiol Biotechnol. 2016 Jun;100(11):4865-73. doi: 10.1007/s00253-015-7261-2. Epub 2016 Jan 12.

引用本文的文献

1
Conformational analysis and intramolecular hydrogen bonding of cis-3-aminoindan-1-ol: a quantum chemical study.顺式-3-氨基茚满-1-醇的构象分析和分子内氢键:量子化学研究。
J Mol Model. 2013 Nov;19(11):4837-47. doi: 10.1007/s00894-013-1989-3. Epub 2013 Sep 13.

本文引用的文献

1
Enantioselective synthesis of syn- and anti-1,3-aminoalcohols via β-aminoketones and subsequent reduction/dynamic kinetic asymmetric transformation.通过β-氨基酮对映选择性合成顺式和反式 1,3-氨基醇,并随后进行还原/动态动力学不对称转化。
J Am Chem Soc. 2010 Nov 3;132(43):15182-4. doi: 10.1021/ja107857v.
2
Allylic C-H amination for the preparation of syn-1,3-amino alcohol motifs.用于制备顺式-1,3-氨基醇基序的烯丙基C-H胺化反应。
J Am Chem Soc. 2009 Aug 26;131(33):11707-11. doi: 10.1021/ja9054959.
3
Rhodium-catalyzed enantioselective and diastereoselective hydrogenation of beta-ketoenamides: efficient access to anti 1,3-amino alcohols.
Angew Chem Int Ed Engl. 2009;48(33):6052-4. doi: 10.1002/anie.200902339.
4
Asymmetric synthesis of acyclic 1,3-amino alcohols by reduction of N-sulfinyl beta-amino ketones. Formal synthesis of (-)-pinidinol and (+)- epipinidinol.通过还原N-亚磺酰基β-氨基酮实现无环1,3-氨基醇的不对称合成。(-)-哌啶醇和(+)-表哌啶醇的形式合成。
J Org Chem. 2008 Dec 19;73(24):9619-26. doi: 10.1021/jo801653c.
5
Directed reductive amination of beta-hydroxy-ketones: convergent assembly of the ritonavir/lopinavir core.β-羟基酮的定向还原胺化反应:利托那韦/洛匹那韦核心结构的汇聚式组装
Org Lett. 2007 Jan 18;9(2):267-70. doi: 10.1021/ol062715y.
6
Practical synthesis of enantiopure gamma-amino alcohols by rhodium-catalyzed asymmetric hydrogenation of beta-secondary-amino ketones.通过铑催化的β-仲氨基酮不对称氢化反应实用合成对映体纯的γ-氨基醇。
Angew Chem Int Ed Engl. 2005 Mar 4;44(11):1687-9. doi: 10.1002/anie.200462178.
7
N- and C-terminal modifications of negamycin.耐霉素的N端和C端修饰
Bioorg Med Chem Lett. 2003 Jul 21;13(14):2413-8. doi: 10.1016/s0960-894x(03)00393-7.
8
Unpredictable stereochemical preferences for mu opioid receptor activity in an exhaustively stereodiversified library of 1,4-enediols.
Org Lett. 2003 Mar 6;5(5):633-6. doi: 10.1021/ol027237f.
9
Novel lopinavir analogues incorporating non-Aromatic P-1 side chains--synthesis and structure--activity relationships.
Bioorg Med Chem Lett. 2002 Nov 4;12(21):3101-3. doi: 10.1016/s0960-894x(02)00643-1.
10
Directed reduction of beta-amino ketones to syn or anti 1,3-amino alcohol derivatives.β-氨基酮定向还原为顺式或反式1,3-氨基醇衍生物。
Org Lett. 2002 Sep 5;4(18):3131-4. doi: 10.1021/ol026456y.