N-(1-cyanooct-2-yl)-4-methylbenzenesulfonamide

• 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-(1-cyanooct-2-yl)-4-methylbenzenesulfonamide
• 英文别名: N-(2-cyanooctyl)-4-methylbenzenesulfonamide；N-[1-(cyanomethyl)heptyl]tosylamide；N-(1-cyanooctan-2-yl)-4-methylbenzenesulfonamide
• 化学式: C₁₆H₂₄N₂O₂S
• 分子量: 308.445
• InChiKey: XQXWTVNKHVALKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  78.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  chloroamine-T 在 碘 、 silica gel 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 生成 N-(1-cyanooct-2-yl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  硅水反应介质中氮丙啶的开环和扩展

  摘要：

  N-甲苯磺酰基ir啶与水溶性亲核试剂的开环反应在二氧化硅-水反应介质中进行。该系统适用于氮丙啶与硫氰酸钾的扩环，从而产生噻唑烷衍生物。

  DOI：

  10.1021/jo061239m

文献信息

• Polystyrene-supported TBD catalyzed ring-opening of N-tosylaziridines with silylated nucleophiles
  作者：Satoru Matsukawa、Takeru Harada、Shiori Yasuda

  DOI：10.1039/c2ob25435b

  日期：——

  Polystyrene-supported TBD (PS-TBD) catalyzes the ring-opening of N-tosylaziridines with silylated nucleophiles to give the corresponding products in high yields. PS-TBD was easily recovered and reused without significant loss of catalytic activity.

  聚苯乙烯支持的TBD（PS-TBD）催化N-托烯基氮杂环的环打开反应，与硅基亲核试剂反应生成相应的产物，产率高。PS-TBD可以容易回收再利用，催化活性没有显著损失。
• TBD-Catalyzed Ring Opening of Aziridines with Silylated Nucleophiles
  作者：S. Matsukawa、H. Takahashi、T. Harada

  DOI：10.1080/00397911.2011.601839

  日期：2013.1

  Abstract The ring opening of N-tosylaziridines with silylated nucleophiles catalyzed by 1,5,7-triazabicyclo[4,4,0]dec-5-ene (TBD) afforded the corresponding β-functionalized sulfonamides in excellent yields under mild reaction conditions. GRAPHICAL ABSTRACT

  摘要 在温和的反应条件下，在 1,5,7-三氮杂双环 [4,4,0]dec-5-烯 (TBD) 催化下，N-甲苯磺酰氮丙啶与甲硅烷基化亲核试剂开环得到相应的 β-官能化磺酰胺，产率极好。图形概要
• Do aziridines require Lewis acids for cleavage with ionic nucleophiles?
  作者：Alakesh Bisai、Ghanshyam Pandey、Manoj K Pandey、Vinod K Singh

  DOI：10.1016/s0040-4039(03)01414-x

  日期：2003.7

  variety of activated aziridines were cleaved by sodium azide and sodium cyanide in aqueous acetonitrile at reflux, in the absence of any Lewis acid, to provide ring-opened products in quantitative yields. However, the reaction was sluggish in the ring opening of unactivated aziridines with sodium azide where the yields could be increased by adding 50 mol% CuCl2·2H2O. The reaction was used to synthesize

  在不存在任何路易斯酸的情况下，在回流下在乙腈水溶液中，将叠氮化钠和氰化钠裂解各种活化的氮丙啶，以定量收率提供开环产物。然而，该反应在未活化的氮丙啶与叠氮化钠的开环中反应缓慢，其中可以通过添加50mol％的CuCl 2 ·2H 2 O来增加产率。该反应用于合成手性二胺。
• Lewis Base Catalyzed Ring Opening of Aziridines with Silylated Nucleophiles
  作者：Satoshi Minakata、Yuriko Okada、Yoji Oderaotoshi、Mitsuo Komatsu

  DOI：10.1021/ol051186f

  日期：2005.8.1

  The ring opening of N-tosylaziridines with trimethylsilylated nucleophiles, catalyzed by N,N,N',N'-tetramethylethylenediamine, led to the production of beta-functionalized sulfonamides in good to excellent yields with high regioselectivity. [reaction: see text]

  N，N，N′，N′-四甲基乙二胺催化的N-甲苯磺酰氮丙啶与三甲基甲硅烷基化的亲核试剂的开环导致β-官能化磺酰胺的生产，具有良好的产率和高的区域选择性。[反应：看文字]
• TTMPP: An efficient organocatalyst in the ring-opening of aziridines with silylated nucleophiles
  作者：Satoru Matsukawa、Kumiko Tsukamoto

  DOI：10.1039/b908322g

  日期：——

  The ring-opening of N-tosylaziridines with silylated nucleophiles catalyzed by tris(2,4,6-trimethoxyphenyl)phosphine (TTMPP) afforded the corresponding β-functionalized sulfonamides in excellent yield under mild reaction conditions.

  N-甲苯磺酰基氮丙啶与甲硅烷基化亲核试剂的开环反应三（2,4,6-三甲氧基苯基）膦 （TTMPP）在温和的反应条件下以优异的产率提供了相应的β-官能化磺酰胺。