New insights into synthesis and oligomerization of epsilon-lactams derived from the terpenoid ketone (-)-menthone

Winnacker Malte; Tischner Andreas; Neumeier Michael; Rieger Bernhard

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New insights into synthesis and oligomerization of epsilon-lactams derived from the terpenoid ketone (-)-menthone

机译：epsilon-inclams衍生自三萜酮（ - ） - 晶体酮的新见解 - ePsilon-inclams - Menthone

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Two regioisomeric lactams, which are derived from terpenoid ketone (-)-menthone in two steps, are oligomerized in an easy acid-induced procedure to obtain oligoamides that contain alkyl groups and stereocenters; for this, a nucleophilic oligomerization via a non-ionic propagating site (neutral conditions) and a polycondensation are also possible. Furthermore, a regioselective synthesis is demonstrated where (-)-menthone is transformed into one of these lactams in a one-step procedure via Beckmann rearrangement without isolation of any oxime intermediate using the reagent hydroxylamine-O-sulfonic acid (HOSA). These concise oligoamide syntheses smooth the way to novel sustainable long-chain polyamides with highly interesting structures.

机译：两种步骤中衍生自三萜酮（ - ） - 介质的衍生自萜类酮（ - ） - 介质的含有烷基诱导的步骤的寡聚醇，以获得含有烷基和立体封闭物的寡聚酰胺; 为此，也可以通过非离子繁殖位点（中性条件）和缩聚的亲核寡聚化。此外，将（ - ） - 介质在一步法中通过Beckmann重新排列在一步程中转化为其中一种内酰胺而没有使用试剂羟胺-O-磺酸（HOSA）来转化到这些内酰胺中的一种中的区域选择性合成。这些简洁的低聚酰胺合成具有高度有趣的结构的新型可持续长链聚酰胺的方式。

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来源
《RSC Advances》 |2015年第95期|共7页
作者
Winnacker Malte; Tischner Andreas; Neumeier Michael; Rieger Bernhard;
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Tech Univ Munich WACKER Lehrstuhl Makromol Chem D-85747 Garching Germany;

Tech Univ Munich WACKER Lehrstuhl Makromol Chem D-85747 Garching Germany;

Tech Univ Munich WACKER Lehrstuhl Makromol Chem D-85747 Garching Germany;

Tech Univ Munich WACKER Lehrstuhl Makromol Chem D-85747 Garching Germany;

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正文语种 eng
中图分类化学;
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1. New insights into synthesis and oligomerization of epsilon-lactams derived from the terpenoid ketone (-)-menthone [J] . Winnacker Malte, Tischner Andreas, Neumeier Michael, RSC Advances . 2015,第95期

机译：epsilon-inclams衍生自三萜酮（ - ） - 晶体酮的新见解 - ePsilon-inclams - Menthone
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5. STEREOCHEMISTRY OF THE ANIONIC OLIGOMERIZATION OF TERT-BUTYL VINYL KETONE (ENOLATES). [D] . BELL, BRUCE CONNARD. 1986

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7. Synthesis and Characterization of a New Chiral Phosphinothiol Ligand Derived from (-)-menthone and Its Palladium(II) and Platinum (II) Complexes [O] . -1

机译：衍生自（ - ） - 薄膜及其钯（II）和铂（II）复合物的新型手性膦醇配体的合成与表征

New insights into synthesis and oligomerization of epsilon-lactams derived from the terpenoid ketone (-)-menthone

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