N-(2-nitrobenzenesulfonyl)-N-(pent-4-enyl)amine | 351035-09-1

• 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-(2-nitrobenzenesulfonyl)-N-(pent-4-enyl)amine
• 英文别名: N-pent-4-enyl-2-nitrobenzenesulfonamide；2-nitro-N-(pent-4-en-1-yl)benzenesulfonamide；2-nitro-N-(pent-4-enyl)benzenesulfonamide；N-nosylpent-4-enamine；Benzenesulfonamide, 2-nitro-N-4-pentenyl-；2-nitro-N-pent-4-enylbenzenesulfonamide
• CAS: 351035-09-1
• 化学式: C₁₁H₁₄N₂O₄S
• 分子量: 270.309
• InChiKey: XWSZBGNLRNLQDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-nitrobenzenesulfonyl)-N-(pent-4-enyl)amine 在 potassium carbonate 、 苯硫酚 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 (-)-(1S,3S,5S)-5-[N-(pent-4-enyl)-N-(benzyloxycarbonyl)amino]-3-(tert-butyl-dimethylsilanyloxy)cyclohept-6-enyl acetate
  参考文献：
  名称：

  Ruthenium catalyzed ring rearrangement: a rapid entry to substituted aza- and oxacycles

  摘要：

  A ring-closing metathesis (RCM) and a ring-opening metathesis (ROM) are combined in a domino process giving access to a variety of aza- and oxacyles, equipped with highly functionalized side chains, starting from readily accessible cyclopentenyl or cycloheptenyl ethers and amines. The role of different protective groups is examined as well as the influence of the relative configuration of stereocenters of the substrate molecules. Substituted 2,5-dihydro-furans and -pyrroles, 1,2,5,6-tetrahydropyranes and -pyridines as well as 2,3,4,7-tetrahydrooxepines are available via this methodology. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00832-3
• 作为产物：
  描述：

  2-硝基苯磺酰胺 在 4-二甲氨基吡啶 、 三乙胺 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 N-(2-nitrobenzenesulfonyl)-N-(pent-4-enyl)amine
  参考文献：
  名称：

  Ruthenium catalyzed ring rearrangement: a rapid entry to substituted aza- and oxacycles

  摘要：

  A ring-closing metathesis (RCM) and a ring-opening metathesis (ROM) are combined in a domino process giving access to a variety of aza- and oxacyles, equipped with highly functionalized side chains, starting from readily accessible cyclopentenyl or cycloheptenyl ethers and amines. The role of different protective groups is examined as well as the influence of the relative configuration of stereocenters of the substrate molecules. Substituted 2,5-dihydro-furans and -pyrroles, 1,2,5,6-tetrahydropyranes and -pyridines as well as 2,3,4,7-tetrahydrooxepines are available via this methodology. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00832-3

文献信息

• Synthesis of Natural-Product-Like Molecules with Over Eighty Distinct Scaffolds
  作者：Daniel Morton、Stuart Leach、Christopher Cordier、Stuart Warriner、Adam Nelson

  DOI：10.1002/anie.200804486

  日期：2009.1

  Seeking scaffold diversity: A synthetic approach for the combinatorial variation of the scaffolds of small molecules is described. Using just six basic reaction types, compounds with 84 distinct scaffolds were prepared. The compounds had many natural‐product‐like structural features including rich stereochemistry, heterocyclic and unsaturated ring systems, and dense functionalization.

  寻求支架多样性：描述了小分子支架组合变异的合成方法。仅使用六种基本反应类型，就制备了具有 84 种不同支架的化合物。这些化合物具有许多类似于天然产物的结构特征，包括丰富的立体化学、杂环和不饱和环系统以及密集的官能化。
• Direct Synthesis of Medium-Bridged Twisted Amides via a Transannular Cyclization Strategy
  作者：Michal Szostak、Jeffrey Aubé

  DOI：10.1021/ol901449y

  日期：2009.9.3

  The sequential RCM to construct a challenging medium-sized ring followed by a transannular cyclization across a medium-sized ring delivers previously unattainable twisted amides from simple acyclic precursors.

  顺序 RCM 构建一个具有挑战性的中等大小的环，然后跨中等大小的环进行跨环环化，从简单的无环前体提供以前无法实现的扭曲酰胺。
• A Fluorous-Tagged “Safety Catch” Linker for Preparing Heterocycles by Ring-Closing Metathesis
  作者：Catherine O’Leary-Steele、Christopher Cordier、Jerome Hayes、Stuart Warriner、Adam Nelson

  DOI：10.1021/ol802848j

  日期：2009.2.19

  fluorous-tagged “safety catch” linker is described for the synthesis of heterocycles with use of ring-closing metathesis. The linker facilitiates the purification of metathesis substrates, the removal of the catalyst, the functionalization of the products, and the release of only metathesis products. The synthesis of a range of heterocycles is described.

  描述了一种氟标记的“安全捕获”连接体，用于使用闭环复分解合成杂环。连接体有利于复分解底物的纯化、催化剂的去除、产物的官能化以及仅复分解产物的释放。描述了一系列杂环的合成。
• Gold-Catalyzed Intramolecular Aminoarylation of Alkenes: CC Bond Formation through Bimolecular Reductive Elimination
  作者：William E. Brenzovich、Diego Benitez、Aaron D. Lackner、Hunter P. Shunatona、Ekaterina Tkatchouk、William A. Goddard、F. Dean Toste

  DOI：10.1002/anie.201002739

  日期：——

  Gold‐ilocks and the 3 mol % catalyst: Bimetallic gold bromides allow the room temperature aminoarylation of unactivated terminal olefins with aryl boronic acids using Selectfluor as an oxidant. A catalytic cycle involving gold(I)/gold(III) and a bimolecular reductive elimination for the key CC bond‐forming step is proposed. dppm= bis(diphenylphosphanyl)methane.

  Gold-ilocks 和 3 mol% 催化剂：双金属溴化金可以在室温下使用 Selectflor 作为氧化剂将未活化的末端烯烃与芳基硼酸进行氨基芳基化。提出了一种涉及金（I）/金（III）的催化循环和关键的C - C键形成步骤的双分子还原消除。dppm=双(二苯基膦酰基)甲烷。
• Total synthesis of the tylophora alkaloids rusplinone, 13aα-secoantofine, and antofine using a multicatalytic oxidative aminochlorocarbonylation/Friedel–Crafts reaction
  作者：Lisa M. Ambrosini、Tim A. Cernak、Tristan H. Lambert

  DOI：10.1016/j.tet.2010.03.021

  日期：2010.6

  A rapid synthetic approach to the tylophora alkaloids antofine and 13aα-secoantofine is presented that makes use of a multicatalytic oxidative aminochlorocarbonylation/Friedel–Crafts reaction as the key step. This reaction, along with a one-pot, three-step telescoped process offers a three or four-pot sequence to access the title compounds in high overall yield.

  提出了一种快速合成tylophora生物碱antofine和13aα-secoantofine的方法，该方法利用了多催化氧化氨基氯羰基化/ Friedel-Crafts反应作为关键步骤。该反应以及一锅，三步伸缩过程提供了三锅或四锅顺序，可以高总收率获得标题化合物。