N,N'-ditosyl-1,5-diaminopentane | 67508-30-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N'-ditosyl-1,5-diaminopentane
• 英文别名: N,N'-pentane-1,5-diylbis(4-methylbenzenesulfonamide)；4-methyl-N-[5-[(4-methylphenyl)sulfonylamino]pentyl]benzenesulfonamide
• CAS: 67508-30-9
• 化学式: C₁₉H₂₆N₂O₄S₂
• mdl: MFCD00196090
• 分子量: 410.558
• InChiKey: BDBVTUYVWGRBDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-ditosyl-1,5-diaminopentane 在 盐酸 、 potassium carbonate 、 肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 103.0h， 生成 N¹,N⁵,N¹¹,N¹⁵-tetra(p-toluenesulfonyl)-1,15-bis(ethylamino)-5,11-diazapentadecane
  参考文献：
  名称：

  T7 RNA polymerase activation and improvement of the transcriptional sequencing by polyamines

  摘要：

  We examined the possibility to improve the effectiveness of the in vitro transcription system using T7 RNA polymerase by coexistence with organic bases. The effect of the additives was evaluated by measuring the amount of RNA products in comparison with that of the control system (without additive). We found that four commercial bases and a series of ethylated polyamine analogues newly designed were active enhancers in the following activation order, 1,8-bis(ethylamino)octane > 1,8-octanediamine > 1,5-bis(ethylamino)-pentane > cadaverine > 1,8-bis(ethylamino)-5,14-diazaoctadecane > spermidine 1,18-bis(ethylamino)-5,14-diazaoctadecane > agmatine. It was shown that RNA products were corresponding, only in the presence of active enhancers, to the Full length size of the template DNA, and that sequencing signals were enhanced by the presence of active enhancers with high fidelity so that the transcriptional sequencing was further refined to be a highly sensitive sequencing method from a small amount of linear dsDNA, These results suggest that T7 RNA polymerase was activated by the specific binding of the polyamine additive to produce RNA transcripts with fidelity to the template DNA. Therefore, it is expected that the transcriptional sequencing in the presence of active enhancers might be a powerful and sensitive method, in place of the prevalent DNA amplification method, for genomic science projects and clinical and practical gene diagnoses. (C) 2000 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0968-0896(00)00156-5
• 作为产物：
  描述：

  1,5-二氨基戊烷 、 对甲苯磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N,N'-ditosyl-1,5-diaminopentane
  参考文献：
  名称：

  酰胺的无过渡金属一步合成

  摘要：

  提出了一种强大的无过渡金属的一步法，用于从磺酰胺和（Z）-1,2-二氯烯烃或炔基氯化物合成乙酰胺。该方法不仅对内部的神经酰胺有效，而且对末端的神经酰胺也适用。各种官能团，甚至乙烯基部分都是相容的，因此，该策略提供了进一步官能化的机会。

  DOI：

  10.1021/acs.joc.8b03192

文献信息

• A Robust One-Step Approach to Ynamides
  作者：Yongliang Tu、Xianzhu Zeng、Hui Wang、Junfeng Zhao

  DOI：10.1021/acs.orglett.7b03665

  日期：2018.1.5

  vinyl dichlorides and electron deficient amides as the starting material is described. In the absence of transition-metal catalyst, the reaction proceeds under mild reaction conditions in open air and thus rendering a convenient operation. This strategy is not only suitable for both terminal and internal ynamide synthesis but also amenable for large-scale preparation. Broad substrate scopes with respect

  描述了一种以廉价和容易获得的化学原料二氯乙烯和缺电子酰胺为原料的合成酰胺的稳健的一步合成策略。在不存在过渡金属催化剂的情况下，反应在温和的反应条件下在露天中进行，因此提供了方便的操作。该策略不仅适用于末端和内部的酰胺合成，而且适用于大规模制备。观察到相对于二氯乙烯和缺电子酰胺而言，底物范围广。
• Copper-Mediated Selective Cross-Coupling of 1,1-Dibromo-1-alkenes and Heteronucleophiles: Development of General Routes to Heterosubstituted Alkynes and Alkenes
  作者：Kévin Jouvin、Alexis Coste、Alexandre Bayle、Frédéric Legrand、Ganesan Karthikeyan、Krishnaji Tadiparthi、Gwilherm Evano

  DOI：10.1021/om3005614

  日期：2012.11.26

  site-selective, double, or alkynylative cross-coupling, therefore providing divergent and straightforward entries to numerous building blocks such as bromoenamides, ynamides, ketene N,N-acetals, bromoenol ethers, ynol ethers, ketene O,O-acetals, or vinylphosphonates and further expanding the copper catalysis toolbox with useful and versatile processes.

  据报道，有效的和通用的程序是将1，1-二溴代烯烃与N-，O-和P-亲核试剂进行交叉偶联。反应条件的微调允许位点选择性，双重或炔基交叉偶联，因此为许多结构单元（如溴酰胺，乙酰胺，乙烯酮N，N-乙缩醛，溴烯醇醚，炔醇醚）提供了分散而直接的入口，乙烯酮O，O-乙缩醛或乙烯基膦酸酯，并通过有用的通用方法进一步扩展了铜催化工具箱。
• Heteroatom-embedded Medium-Sized Cycloalkynes: Concise Synthesis, Structural Analysis, and Reactions
  作者：Runyan Ni、Naoto Mitsuda、Takeru Kashiwagi、Kazunobu Igawa、Katsuhiko Tomooka

  DOI：10.1002/anie.201409910

  日期：2015.1.19

  A variety of medium‐sized cycloalkynes were efficiently synthesized by the double Nicholas reaction of cobalt complex and bis(hetero)substituted acyclic compound. The alkyne moiety within the ring has a unique bent structure and high reactivity toward cycloaddition reactions. Furthermore, preparation of multifunctionalized alkynes was achieved by embedding the cycloalkyne within a peptide chain.

  通过钴配合物和双（杂）取代的无环化合物的双尼古拉斯反应，可以有效地合成各种中等大小的环炔烃。环中的炔烃部分具有独特的弯曲结构，并且对环加成反应具有很高的反应性。此外，通过将环炔嵌入肽链中来实现多功能化炔的制备。
• Preferential Introduction of a Pyridylmethyl Group into Sulfonamides as an Approach to an Intramolecular Transimination
  作者：Masaaki Iwata、Hiroyoshi Kuzuhara

  DOI：10.1246/bcsj.55.2153

  日期：1982.7

  N,N′-Bis(p-tolylsulfonyl)-α-ω-alkanediamine disodium salts (n=3, 4, 5, 6, 7, 8, 9, 10) were subjected to monopyridylmethylation by the reaction with 5′-deoxy-5′-chloro- or 5′-deoxy-2′-chloro-3,4′-O-isopropylidenepyridoxine hydrochloride, accompanied by the corresponding bispyridylmethylation. Monopyridylmethylation became remarkable for longer methylene chains of the diamine. Thus, introduction of an amino group protected by a sulfonyl group at the end of either the C2- or the C5-side chains of pyridoxine derivatives was achieved.

  N,N′-双(对甲苯磺酰基)-α-ω-烷二胺二钠盐(n=3, 4, 5, 6, 7, 8, 9, 10)通过与 5′-脱氧-5′-氯或 5′-脱氧-2′-氯-3、4′-O-isopropylidenepyridoxine hydrochloride，同时进行相应的双吡啶基甲基化。当二胺的亚甲基链较长时，单吡啶基甲基化效果显著。因此，在吡哆醇衍生物的 C2-或 C5-侧链末端引入受磺酰基保护的氨基是可以实现的。
• Thieme Chemistry Journals Awardees: Where Are They Now? One-Pot Synthesis of Versatile Buckle Units for Click Chemistry: 4,8-Diazacyclononynes (DACNs)
  作者：Kazunobu Igawa、Katsuhiko Tomooka、Shin Aoyama、Yuuya Kawasaki、Takeru Kashiwagi、Yuki Seto、Runyan Ni、Naoto Mitsuda

  DOI：10.1055/s-0036-1588839

  日期：2017.10

  Newly designed buckle units for copper-free click chemistry: 4,8-diazacyclononynes (DACNs) were efficiently synthesized with a one-pot procedure from commercially available 2-butyne-1,4-diol. The synthesized DACNs possess versatile connectors for the introduction of functional units and exhibit high click reactivity.

  新设计的用于无铜点击化学的扣单元：4,8-二氮杂环壬炔 (DACN) 是通过一锅法从市售的 2-丁炔-1,4-二醇有效合成的。合成的 DACN 具有用于引入功能单元的多功能连接器，并表现出高点击反应性。