Ethyl trifluoromethanesulfonamide | 34310-30-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Ethyl trifluoromethanesulfonamide
• 英文别名: N-ethyltrifluoromethanesulfonamide；N-ethyltriflamide；Ethyl(trifluoromethylsulfonyl)amine；N-ethyl-1,1,1-trifluoromethanesulfonamide
• CAS: 34310-30-0
• 化学式: C₃H₆F₃NO₂S
• 分子量: 177.147
• InChiKey: ADQRHLTXZPZLHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-4-(2-羟乙基)-2,2-二甲基-1,3-二氧戊环 、 Ethyl trifluoromethanesulfonamide 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 3.3h， 以93%的产率得到N-{2-[(4S)-2,2-Dimethyl-1,3-dioxolane-4-yl]ethyl}-N-ethyltrifluoromethanesulfonamide
  参考文献：
  名称：

  An Improved Synthesis of (3S,12S)-N ^¹ ,N ¹⁴-Diethyl-3,12-dihydroxy-homospermine, a Polyamine Analogue Therapeutic Agent

  摘要：

  本文描述了 N 1,N 14-二乙基高精胺羟基化类似物 (3S,12S)-N 1,N 14-二乙基-3,12-二羟基高精胺的合成过程。这种高精胺衍生物的关键步骤是用两个等量的 N-[(3S)-3,4-环氧丁基]-N-乙基三氟甲基磺酰胺对 N,N"-二苄基高精胺进行烷基化。

  DOI：

  10.1055/s-2001-14570
• 作为产物：
  描述：

  三氟甲磺酸酐 、 乙胺 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 Ethyl trifluoromethanesulfonamide
  参考文献：
  名称：

  Use of the Mitsunobu reaction in the synthesis of polyamines

  摘要：

  The Mitsunobu reaction has been used in the synthesis of polyamine analogues. The synthesis of the (R,R), (S,S) and meso- isomers of a tetraamine are described. The chemistry was used to synthesize a fluorinated polyamine analog and a hexaamine.

  DOI：

  10.1016/s0040-4020(01)85630-1

文献信息

• Use of the Mitsunobu reaction in the synthesis of polyamines
  作者：Michael L. Edwards、David M. Stemerick、James R. McCarthy

  DOI：10.1016/s0040-4020(01)85630-1

  日期：1994.1

  The Mitsunobu reaction has been used in the synthesis of polyamine analogues. The synthesis of the (R,R), (S,S) and meso- isomers of a tetraamine are described. The chemistry was used to synthesize a fluorinated polyamine analog and a hexaamine.
• Synthesis and Evaluation of Hydroxylated Polyamine Analogues as Antiproliferatives
  作者：Raymond J. Bergeron、Ralf Müller、Jörg Bussenius、James S. McManis、Ronald L. Merriman、Richard E. Smith、Hua Yao、William R. Weimar

  DOI：10.1021/jm990375z

  日期：2000.1.1

  The synthesis of four hydroxylated polyamine analogues, (2R,10R)-N-1,N-11-diethyl-2,10-dihydroxynorspermine, droxynorspermine, (2S,10S)-N-1,N-11-diethyl-2,10-dihydroxynospermine, (3S, 12S)-N-1,N-14-diethyl-3, 12-dihydroyhomospermine, and (3R,12R)-N-1-N-14-diethyl-3,12-dihgrdroxyhomospermine, is described along with their impact on the growth and polyamine metabolism of L1210 murine leukemia cells. Four different synthetic approaches are set forth, two each for the hydroxylated norspermines and for the hydroxylated homospermines. The key step in the assembly of the norspermines was the coupling of either N-[2R)-2,3-epoxypropyl]-N-ethyl p-toluenesulfonamide or N-[(2S)-2, 3-epoxypropyl]-N-ethyl trifluoromethane sulfonamide to N,N'-dibenzyl-1,3-diaminopropane. The key step with homospermines employed alkylation of putrescine with (3S)-N-(benzyloxycarbonyl)-N-ethyl-3,4-epoxybutylamine or of N,N'-bis(mesitylenesulfonyl)-1,4-butanediamine with (2R)-2-benzyloxy-4-[N-(mesitylenesulfonyl], All of the hydroxylated analogues were active against L1210 cells with 96-h IC50 values of less than or equal to 2 mu M, and they also effectively reduced putrescine and spermidine, although the effect on spermine pools ranged from moderate to insignificant. Interestingly, the impact of the hydroxylated analogues an ornithine decarboxylase (ODC) was significantly less than that of unhydroxylated parent drug (e.g., (NN11)-N-1-diethylnorspermine [DENSPM]) at 1 mu M ; however, S-adenosylmethionine decarboxylase (AdoMetDC) depletion was nearly identical to what was observed in cells treated with parent drug. The most notable difference between the parent and hydroxylated analogues was seen with spermidine/spermine N-1-acetyltransferase (SSAT) upregulation in the DENSPM series. The hydroxylated analogues, especially (R,R)-(HO)(2)-DENSPM, were much less effective at upregulation than the parent DENSPM. Finally, a comparison of the toxicity of (RP)-(HO)(2)DENSPM with that of DENSPM at subchronic doses revealed that the neurological effects seen with DENSPM were now absent.
• An Improved Synthesis of (3<b><i>S</i></b>,12<i>S</i>)-<i>N</i> ^¹,<i>N</i> ¹⁴-Diethyl-3,12-dihydroxy-homospermine, a Polyamine Analogue Therapeutic Agent
  作者：Raymond Bergeron、Ralf Müller、James McManis、Guo Yao、Guangfei Huang

  DOI：10.1055/s-2001-14570

  日期：——

  The synthesis of a hydroxylated analogue of N 1,N 14-diethylhomospermine, (3S,12S)-N 1,N 14-diethyl-3,12-dihydroxyhomospermine, is described. The key step in the assembly of this homospermine derivative involves alkylation of N,N"-dibenzylputrescine with two equivalents of N-[(3S)-3,4-epoxybutyl]-N-ethyltrifluoromethanesulfonamide.

  本文描述了 N 1,N 14-二乙基高精胺羟基化类似物 (3S,12S)-N 1,N 14-二乙基-3,12-二羟基高精胺的合成过程。这种高精胺衍生物的关键步骤是用两个等量的 N-[(3S)-3,4-环氧丁基]-N-乙基三氟甲基磺酰胺对 N,N"-二苄基高精胺进行烷基化。