N-(2-cyano-1-phenylethyl)-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-(2-cyano-1-phenylethyl)-4-methylbenzenesulfonamide
• 化学式: C₁₆H₁₆N₂O₂S
• 分子量: 300.381
• InChiKey: QXKAWNBZHYMQKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  78.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-cyano-1-phenylethyl)-4-methylbenzenesulfonamide 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 (+/-)-3-phenyl-3-(toluene-4-sulfonylamino)-propionic acid
  参考文献：
  名称：

  Synthesis and microbial transformation of β-amino nitriles

  摘要：

  Rhodococcus equi A4, Rhodococcus erythropolis NCIMB 11540 and Rhodococcus sp. R312 were investigated towards their ability to produce beta-amino amides and acids from beta-amino nitriles. The microorganisms show comparable trends: five-membered alicyclic 2-amino nitriles were transformed significantly faster than the six-membered compounds and the products of trans-2-amino nitriles (amides and acids) were formed considerably faster than the cis-counterparts (amides). The trans-five membered nitrites gave the amides (1b, 5b) in excellent enantiomeric excess (94-99%), the biotransformation of trans-six membered substrates resulted in the formation of the acid (3c, 7c) in excellent ee (87-99%). The ee's of the cis-compounds were throughout lower. Fifteen new substances were synthesized and characterized in the course of this work. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.02.057
• 作为产物：
  描述：

  (肉)桂腈 在 甲醇 、 copper acetylacetonate 、 magnesium 作用下， 反应 2.0h， 生成 N-(2-cyano-1-phenylethyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Regiospecific Reductive Cleavage of the C(2)−N Bond of Aziridines Substituted with an Electron Acceptor Mediated by Mg/MeOH

  摘要：

  DOI：

  10.1021/jo9806963

文献信息

• Catalytic cyanomethylation of carbonyl compounds and imines with highly basic phosphine
  作者：Satoru Matsukawa、Eri Kitazaki

  DOI：10.1016/j.tetlet.2008.02.155

  日期：2008.4

  A highly basic phosphine, tris(2,4,6-trimethoxy phenyl)phosphine (TTMPP), catalyzes cyanomethylation using trimethylsilylacetonitrile (TMSCH2CN) to give the corresponding products in good to high yields, with both carbonyl compounds and imines.

  高碱性膦三（2,4,6-三甲氧基苯基）膦（TTMPP）使用三甲基甲硅烷基乙腈（TMSCH 2 CN）催化氰基甲基化，从而以羰基化合物和亚胺的高收率得到相应的产物。
• 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。
• 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。
• Lithium Perchlorate Catalyzed Regioselective Ring Opening of Aziridines with Sodium Azide and Sodium Cyanide
  作者：Jhillu S. Yadav、Basi V. Subba Reddy、G. Parimala、P. Venkatram Reddy

  DOI：10.1055/s-2002-35216

  日期：——

  Aziridines react smoothly with sodium azide and sodium cyanide in the presence of catalytic amount of lithium perchlorate under essentially mild and neutral reaction conditions to afford the corresponding β-azido and β-cyaoamines in high yields with high regioselectivity.

  在催化量的高氯酸锂存在下，氮丙啶与叠氮化钠和氰化钠在基本上温和和中性的反应条件下平稳反应，以高产率和高区域选择性提供相应的 β-叠氮基和 β-氰胺。
• Ring Opening and Expansion of Aziridines in a Silica−Water Reaction Medium
  作者：Satoshi Minakata、Takahiro Hotta、Yoji Oderaotoshi、Mitsuo Komatsu

  DOI：10.1021/jo061239m

  日期：2006.9.1

  Ring-opening reactions of N-tosylaziridines with water-soluble nucleophiles proceeded in a silica−water reaction medium. The system is applicable to a ring expansion of an aziridine with potassium thiocyanate, leading to a thiazolidine derivative.

  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。