[(1R)-1-cyanobutyl] 4-methylbenzenesulfonate | 133870-86-7

• 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: [(1R)-1-cyanobutyl] 4-methylbenzenesulfonate
• CAS: 133870-86-7
• 化学式: C₁₂H₁₅NO₃S
• 分子量: 253.322
• InChiKey: IVIOYQGCQQZRKL-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  75.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(1R)-1-cyanobutyl] 4-methylbenzenesulfonate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以56.1%的产率得到(2S)-2-propylaziridine
  参考文献：
  名称：

  A convenient preparation of 2-substituted (S)-aziridines

  摘要：

  2-Monosubstituted (S)-aziridines (S)-3 were obtained by hydrogenation of (R)-2-sulfonyloxynitriles (R)-2 with LiAlH4 in good chemical yields and high enantiomeric excess.

  DOI：

  10.1016/0957-4166(94)00385-o
• 作为产物：
  描述：

  (R)-(+)-2-羟基戊腈 、 对甲苯磺酰氯 在 吡啶 作用下， 生成 [(1R)-1-cyanobutyl] 4-methylbenzenesulfonate
  参考文献：
  名称：

  A convenient preparation of 2-substituted (S)-aziridines

  摘要：

  2-Monosubstituted (S)-aziridines (S)-3 were obtained by hydrogenation of (R)-2-sulfonyloxynitriles (R)-2 with LiAlH4 in good chemical yields and high enantiomeric excess.

  DOI：

  10.1016/0957-4166(94)00385-o

文献信息

• Stereoselective substitution of (R)-2-(sulfonyloxy)nitriles with sulfur nucleophiles
  作者：Franz Effenberger、Sebastian Gaupp

  DOI：10.1016/s0957-4166(99)00154-8

  日期：1999.5

  Optically active 2-(4-toluenesulfonyloxy)- and (4-nitrobenzenesulfonyloxy)nitriles (R)-3 and (R)-4, which were obtained from (R)-cyanohydrins (R)-2 by sulfonylation, react with sulfur nucleophiles such as potassium thioacetate, potassium ethylxanthogenate, potassium thiocyanate, as well as thioalcohols and thiophenol in a typical S(N)2 manner to give the (S)-2-sulfanyl nitriles (S)-7-9 and (S)-11-13 in good chemical yields and enantiomeric excesses. Even (R)-2-methyl-2-(methanesulfonyloxy)hexanenitrile (R)-6, derived from ketone cyanohydrin (R)-5, reacts with potassium thioacetate to yield (S)-2-acetylthio-2-methylhexanenitrile (S)-10 with 97% ee. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Effenberger, Franz; Stelzer, Uwe, Chemische Berichte, 1993, vol. 126, # 3, p. 779 - 786
  作者：Effenberger, Franz、Stelzer, Uwe

  DOI：——

  日期：——
• A convenient synthesis of (S)-2-Azidonitriles, (S)-2-aminonitriles and (S)-1,2-diamines
  作者：F. Effenberger、Andreas Kremser、Uwe Stelzer

  DOI：10.1016/0957-4166(96)00044-4

  日期：1996.2

  (S)-2-Azidonitriles (S)-4 are easily accessible from (R)-2-(sulfonyloxy)nitriles (R)-2 by nucleophilic substitution with alkali azides 3 under complete inversion of configuration. The azidonitriles (S)-4 can be converted by catalytic hydrogenation into (S)-2-aminonitriles (S)-8 and by hydrogenation using LiAlH4 into (S)-1, 2-diaminoalkanes (S)-9, respectively, both, (S)-8 and (S)-9, isolated as hydrochlorides. Hydrolysis of the aminonitrile hydrochlorides (S)-8 HCl in a saturated solution of HC1 in alcohol gives (S)-2-amino carboxamide hydrochlorides(S)-10 . HCl with enantiomeric excesses >99% after recrystallization.
• Preparation of (S)-fluoronitriles
  作者：Uwe Stelzer、Franz Effenberger

  DOI：10.1016/s0957-4166(00)82327-7

  日期：1993.2

  (S)-2-fluoronitriles (S)-4 are obtained in good chemical and high optical yields from (R)-cyanohydrins (R)-2 or (R)-cyanohydrin trimethylsilylethers (R)-3 by fluorination with DAST or by nucleophilic substitution of alpha-sulfonyloxynitriles (R)-6, 7 with fluoride on polymeric supports (Amberlyst A-26 F-) under inversion of configuration of the starting cyanohydrins.
• Effenberger, Franz; Stelzer, Uwe, Angewandte Chemie, 1991, vol. 103, # 7, p. 866 - 867
  作者：Effenberger, Franz、Stelzer, Uwe

  DOI：——

  日期：——