(S)-4-methyl-3-tosylamino-pentane-1-nitrile | 875438-79-2

• 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: (S)-4-methyl-3-tosylamino-pentane-1-nitrile
• 英文别名: (3R)-(p-toluenesulfonyl)amino-4-methylpentionitrile；(3R)-3-(p-toluenesulfonyl)amino-4-methylpentanenitrile；N-[(2R)-1-cyano-3-methylbutan-2-yl]-4-methylbenzenesulfonamide
• CAS: 875438-79-2
• 化学式: C₁₃H₁₈N₂O₂S
• 分子量: 266.364
• InChiKey: WSPDGDMKYQDJSV-CYBMUJFWSA-N

物化性质

• 熔点：
  85-87 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  428.4±55.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  (S)-4-methyl-3-tosylamino-pentane-1-nitrile 在 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以85%的产率得到(S)-4-methyl-3-tosylamino-1-pentanal
  参考文献：
  名称：

  从α-氨基酸对映体纯的N-甲苯磺酰氮杂环丁烷的简便合成路线

  摘要：

  以非常简单的化学方法，从手性α-氨基酸开始，以良好的总收率描述了各种手性2-取代-和2,4-二取代-N-甲苯磺酰氮杂环丁烷（ee> 99％）的通用且方便的合成途径。

  DOI：

  10.1016/j.tetlet.2007.02.033
• 作为产物：
  描述：

  L-缬氨醇 在 吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-4-methyl-3-tosylamino-pentane-1-nitrile
  参考文献：
  名称：

  Stereoselective synthesis of 2,4,5-trisubstituted piperidines by carbonyl ene and Prins cyclisations

  摘要：

  浓盐酸催化的醛类3a–e的环化反应在2-取代基较小的情况下，主要生成全顺式的2,4,5-三取代哌啶4a–e，而使用MeAlCl2在氯仿回流条件下催化则生成反式哌啶5a–e，差异体比可高达99 : 1。

  DOI：

  10.1039/b515547a

文献信息

• Synthesis of Fused and Linked Bicyclic Nitrogen Heterocycles by Palladium-Catalyzed Domino Cyclization of Propargyl Bromides
  作者：Akinori Okano、Koji Tsukamoto、Shohei Kosaka、Hatsuo Maeda、Shinya Oishi、Tetsuaki Tanaka、Nobutaka Fujii、Hiroaki Ohno

  DOI：10.1002/chem.201000653

  日期：——

  The palladium(0)‐catalyzed direct construction of bicyclic heterocycles is described. Treatment of propargyl bromides that have nucleophilic functional groups connected by two or three carbon atoms with catalytic [Pd(PPh3)4] affords bis‐cyclization products in good yields. The desired bicyclic heterocycles can be obtained selectively when using substrates with appropriate nucleophilic groups. We also

  描述了钯（0）催化的双环杂环的直接结构。通过催化[Pd（PPh 3）4 ]处理具有两个或三个碳原子相连的亲核官能团的炔丙基溴，可以得到双环化产物，收率很高。当使用具有适当亲核基团的底物时，可以选择性地获得所需的双环杂环。我们还描述了在无碱条件下2-炔基氮杂环丁烷衍生物与催化量的[Pd（PPh 3）4 ]的反应，该反应提供了与相应的炔丙基溴相同的稠合杂环。
• Synthesis of novel N-protected β3-amino nitriles: study of their hydrolysis involving a nitrilase-catalyzed step
  作者：Maité Sylla-Iyarreta Veitía、Pierre Louis Brun、Pierre Jorda、Annie Falguières、Clotilde Ferroud

  DOI：10.1016/j.tetasy.2009.07.045

  日期：2009.9

  Several commercially available nitrilases were investigated with regard to their potential to hydrolyze N-protected beta(3)-amino nitriles into their corresponding N-protected beta(3)-amino acids.The biotransformations were obtained in different proportions depending oil the nitrilase involved The best hydrolysis results were achieved for the N-Cbz-beta(3)-amino nitrile from i-alanine using the NIT-107, in a phosphate buffer at 0 05 M However, no biotransformation into the corresponding acids was observed for the N-sulfonylamide beta(3)-amino nitriles. Two simple and efficient procedures to prepare the beta(3)-amino nitriles from their analogous alpha-amino acids are described Thirty four new substances were synthesized and characterized over the course of this work. (C) 2009 Elsevier Ltd All rights reserved
• Stereoselective Synthesis of 2,4,5-Trisubstituted Piperidines via Radical Cyclization
  作者：Maria-Eleni Ragoussi、Stephen M. Walker、Andrea Piccanello、Benson M. Kariuki、Peter N. Horton、Neil Spencer、John S. Snaith

  DOI：10.1021/jo101631y

  日期：2010.11.5

  A novel approach to 2,4,5-trisubstituted piperidines is reported, involving the 6-exo cyclization of stabilized radicals onto alpha,beta-unsaturated esters. Only two of the four possible diastereoisomers are observed, with diastereomeric ratios ranging from 3:2 to 40:1 when the radical stabilizing group is vinyl or phenyl. Cyclization of a (triethylsilyl)vinyl-stabilized radical gives the corresponding piperidine radical as a single diastereoisomer that may either be trapped by tributyltin hydride to afford the 2,4,5-trisubstituted piperidine or undergo a second 5-endo cyclization onto the (triethylsilyl)vinyl substituent to produce the 3,5,7-trisubstituted octahydro[2]pyrindene as a single diastereoisomer.
• Synthesis and biological evaluation of reversible inhibitors of IdeS, a bacterial cysteine protease and virulence determinant
  作者：Kristina Berggren、Björn Johansson、Tomas Fex、Jan Kihlberg、Lars Björck、Kristina Luthman

  DOI：10.1016/j.bmc.2009.03.026

  日期：2009.5

  Analogues of the irreversible protease inhibitors TPCK and TLCK have been synthesized and tested as inhibitors of the bacterial cysteine protease IdeS excreted by Streptococcus pyogenes. Eight compounds were identified as inhibitors of IdeS in an in vitro assay. The most potent compounds contained an aldehyde function, thus acting as efficient reversible inhibitors, nitrile and azide derivatives showed moderate activity. (C) 2009 Elsevier Ltd. All rights reserved.