Cyclic cis-1,3-diamines are versatile building blocks frequently found in natural molecules or biologically active compounds. In comparison with widely studied 1,2-diamines, and despite their chemical similarity, 1,3-diamines have been investigated less intensively probably because of a lack of general synthetic procedures giving access to these compounds with good levels of chemo-, regio-, and stereocontrol. In this Account we will give a general overview of the biological interest of cyclic cis-1,3-diamines. We will then describe the synthesis and potential applications of these compounds with a particular focus on the work realized in our laboratory. 1 Introduction 2 Biological Relevance of the cis-1,3-Diamine Motif 3 Classical Synthetic Strategies towards cis-1,3-Diamines 4 N–N Bond Cleavage of Bicyclic Hydrazines: A Versatile Method to Access cis-1,3-Diamines 4.1 Preparation of Five-Membered Cyclic cis-1,3-Diamino Alcohols 4.2 Access to Fluorinated 1,3-cis-Diaminocyclopentanes 4.3 Synthesis of cis-1,3-Diaminocyclohexitols 4.4 Formation of Cyclic cis-3,5-Diaminopiperidines 5 Applications of Cyclic cis-1,3-Diamines 5.1 Small-Molecular RNA Binders 5.2 Fluorinated 1,3-Diamino Cyclopentanes as NMR Probes 6 Concluding Remarks

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双环肼衍生的环状顺-1,3-二胺：合成与应用

环状顺式 1,3-二胺是常见于天然分子或生物活性化合物中的通用结构单元。与广泛研究的 1,2-二胺相比，尽管它们具有化学相似性，但对 1,3-二胺的研究较少，可能是因为缺乏通用合成程序来获得这些具有良好化学、区域- ，和立体声控制。在本报告中，我们将概述环状 cis-1,3-二胺的生物学意义。然后，我们将描述这些化合物的合成和潜在应用，特别关注我们实验室实现的工作。1 引言 2 顺式 1,3-二胺基序的生物学相关性 3 顺式 1,3-二胺的经典合成策略 4 双环肼的 N-N 键断裂：