苯磺酰胺,N-[(1R,2R)-2-氰基环己基]-4-甲基-,rel- | 132161-94-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯磺酰胺,N-[(1R,2R)-2-氰基环己基]-4-甲基-,rel-
• 英文名称: N-(2-cyanocyclohexyl)-4-methylbenzenesulfonamide
• 英文别名: N-[(1R,2R)-2-cyanocyclohexyl]-4-methylbenzenesulfonamide
• CAS: 132161-94-5
• 化学式: C₁₄H₁₈N₂O₂S
• 分子量: 278.375
• InChiKey: OIOWYXSMZBQFBW-GXTWGEPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  苯磺酰胺,N-[(1R,2R)-2-氰基环己基]-4-甲基-,rel- 在 二异丁基氢化铝 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 13.33h， 生成 (+/-)-trans-2-(N-allyl-N-tosylamino)cyclohexanecarbaldehyde
  参考文献：
  名称：

  An approach to preparation of trans-DHQs via ring-opening of meso-N-sulfonylaziridines

  摘要：

  作为对手性选择性合成反式-十氢喹啉（DHQs）的一种方法，研究了在催化条件下使用各种碳亲核试剂对中间体meso-环氧丙烷（5）进行非对称化。通过在非拉丁手性配体存在下加入TMSCN和YbCl3，得到了具有最高达40% ee的腈13。腈13是一条新路线中的关键中间体，用于合成反式-DHQs。

  DOI：

  10.1135/cccc2011013
• 作为产物：
  描述：

  2-氨基-1-环己烯甲腈 在 盐酸 、 sodium cyanoborohydride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 苯磺酰胺,N-[(1R,2R)-2-氰基环己基]-4-甲基-,rel-
  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

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。
• 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。
• 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]