1,1,1-三氟-3-硝基-丁烷-2-醇 | 434-39-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 1,1,1-三氟-3-硝基-丁烷-2-醇
• 英文名称: 3-nitro-1,1,1-trifluoro-2-butanol
• 英文别名: 3-nitro-1,1,1-trifluorobutan-2-ol；1,1,1-trifluoro-3-nitro-butan-2-ol；1,1,1-Trifluor-3-nitro-butan-2-ol；1,1,1-Trifluoro-3-nitrobutan-2-ol
• CAS: 434-39-9
• 化学式: C₄H₆F₃NO₃
• 分子量: 173.092
• InChiKey: PKQGAGPKSOAOPY-UHFFFAOYSA-N

物化性质

• 沸点：
  85-87 °C(Press: 25 Torr)
• 密度：
  1.418±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2905590090

反应信息

• 作为反应物：
  描述：

  1,1,1-三氟-3-硝基-丁烷-2-醇 在 四磷十氧化物 作用下， 生成 (E)-1,1,1-trifluoro-3-nitrobut-2-ene
  参考文献：
  名称：

  CH [CH（CF 3）NH] Gly-肽：合成和构象分析†

  摘要：

  Ψ[CH（CF 3）NH] Gly肽是具有立体构象的三氟乙胺基团作为天然肽键替代物的概念上新型的拟肽类化合物，它是通过将α-氨基酸酯立体选择性地添加到反式-3,3,3-三氟-1-硝基丙烯。通过ROESY实验检测到的远距离核Overhauser效应提供了证据，证明incorporating [CH（CF 3）NH] Gly-四肽模型结合了二肽环的三氟乙胺前甘氨酸可以通过展开构象和折叠构象的集合来表示。后者是由羰基和三氟乙胺单元的氨基质子之间形成氢键驱动的。MD计算表明，所有L肽均采用折叠的β转角结构的构象体。另一方面，在Pro残基处的D-立体化学诱导由第二氢键的形成驱动的向β发夹构象的自然折叠，而与立体生成肽键替代的立体化学无关。

  DOI：

  10.1039/b901718f
• 作为产物：
  描述：

  硝基乙烷 、 2,2,2-三氟乙醛 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 5.0h， 以8.2%的产率得到1,1,1-三氟-3-硝基-丁烷-2-醇
  参考文献：
  名称：

  Kingsbury, Charles A.; Sopchik, Alan E.; Underwood, Gary, Journal of the Chemical Society. Perkin transactions II, 1982, p. 867 - 874

  摘要：

  DOI：

文献信息

• A Convenient Synthesis of Trifluoromethylated Pyrroles and Porphyrins
  作者：Noboru Ono、Hisayuki Kawamura、Kazuhiro Maruyama

  DOI：10.1246/bcsj.62.3386

  日期：1989.10

  4-Alkyl-3-trifluoromethyl-2-pyrrolecarboxylic acid esters (2) were conveniently prepared by the reaction of trifluoromethylated β-nitro acetates (1) with ethyl isocyanoacetate. The pyrroles were converted into the corresponding porphyrins via tetramerization of 2-(hydroxymethyl)pyrroles.

  4-烷基-3-三氟甲基-2-吡咯甲酸酯（2）可通过三氟甲基化β-硝基乙酸酯（1）与异氰乙酸乙酯反应方便地制备。吡咯通过 2-（羟甲基）吡咯的四聚作用转化为相应的卟啉。
• Inhibition of <scp>dd</scp>-Peptidases by a Specific Trifluoroketone: Crystal Structure of a Complex with the <i>Actinomadura</i> R39 <scp>dd</scp>-Peptidase
  作者：Liudmila Dzhekieva、S. A. Adediran、Raphael Herman、Frédéric Kerff、Colette Duez、Paulette Charlier、Eric Sauvage、R. F. Pratt

  DOI：10.1021/bi400048s

  日期：2013.3.26

  was a potent inhibitor, but rather unexpectedly from precedent, the trifluoroketone [d-α-aminopimelyl(1,1,1-trifluoro-3-amino)butan-2-one] was also very effective. Taking into account competing hydration, we found the trifluoroketone was the strongest inhibitor of the Actinomadura R39 dd-peptidase, with a subnanomolar (free ketone) inhibition constant. A crystal structure of the complex between the

  细菌抑制剂DD -peptidases代表潜在的抗生素。在寻求替代β内酰胺类，我们已经调查了一系列设计成在与反应，以生成过渡态类似物的结构的化合物的DD -peptidases。该化合物包含肽聚糖模拟物特异性手柄和能够将四面体阴离子递送至酶活性位点的弹头的组合。后者包括一种硼酸、两种醇、一种醛和一种三氟酮。针对两种低分子量 C 类dd -肽酶测试了化合物。正如之前的观察所预期的那样，硼酸是一种有效的抑制剂，但出乎意料的是，三氟酮 [ d-α-aminopimelyl(1,1,1-trifluoro-3-amino)butan-2-one] 也非常有效。考虑到竞争的水合作用，我们发现trifluoroketone是最强的抑制剂马杜拉放线R39 DD 1-肽，具有亚纳摩尔（游离酮）抑制常数。三氟酮和 R39 酶之间的复合物的晶体结构表明，确实与活性位点丝氨酸亲核试剂形成了四面体加​​合物。的t
• Peptidomimetic Inhibitors of the Human Cytomegalovirus Protease
  作者：William Ogilvie、Murray Bailey、Marc-André Poupart、Abraham、Amit Bhavsar、Pierre Bonneau、Josée Bordeleau、Yves Bousquet、Catherine Chabot、Jean-Simon Duceppe、Gulrez Fazal、Sylvie Goulet、Chantal Grand-Maître、Ingrid Guse、Ted Halmos、Pierre Lavallée、Michael Leach、Eric Malenfant、Jeff O'Meara、Raymond Plante、Céline Plouffe、Martin Poirier、François Soucy、Christiane Yoakim、Robert Déziel

  DOI：10.1021/jm970104t

  日期：1997.12.1

  The development of peptidomimetic inhibitors of the human cytomegalovirus (HCMV) :protease showing sub-micromolar potency in an enzymatic assay is described. Selective substitution of the amino acid residues of these inhibitors led to the identification of tripeptide inhibitors showing improvements in inhibitor potency cf 27-fold relative to inhibitor 39 based upon the natural tetrapeptide sequence. Small side chains at P-1 were well tolerated by this enzyme, a fact consistent with previous observations. The S-2 binding pocket of HCMV protease was very permissive, tolerating lipophilic and basic residues. The substitutions tried at P-3 indicated that a small increase in inhibitor potency could be realized by the substitution of a tert-leucine residue for valine. Substitutions of the N-terminal capping group did not significantly affect inhibitor potency. Pentafluoroethyl ketones, alpha,alpha-difluoro-beta-keto amides, phosphonates and a-keto amides were all effective substitutions for the activated carbonyl component and gave inhibitors which were selective for HCMV protease. A slight increase in potency was observed by lengthening the P-1' residue of the alpha-keto amide series of inhibitors. This position also tolerated a variety of groups making this a potential site for future modifications which could modulate the physicochemical properties of these molecules.
• Design, synthesis, and evaluation of trifluoromethyl ketones as inhibitors of SARS-CoV 3CL protease
  作者：Yi-Ming Shao、Wen-Bin Yang、Tun-Hsun Kuo、Keng-Chang Tsai、Chun-Hung Lin、An-Suei Yang、Po-Huang Liang、Chi-Huey Wong

  DOI：10.1016/j.bmc.2008.02.040

  日期：2008.4

  A series of trifluoromethyl ketones as SARS-CoV 3CL protease inhibitors was developed. The inhibitors were synthesized in four steps from commercially available compounds. Three different amino acids were explored in the P1-position and in the P2-P4 positions varying amino acids and long alkyl chain were incorporated. All inhibitors were evaluated in an in vitro assay using purified enzyme and fluorogenic substrate peptide. One of the inhibitors showed a time-dependent inhibition, with a K-i value of 0.3 mu M after 4 h incubation. (c) 2008 Published by Elsevier Ltd.
• The Ethanolysis of 1,1,1-Trifluoro-2,3-epoxybutane and 2-Methyl-1,1,1-trifluoro-2,3-epoxypropane
  作者：E. T. McBee、C. E. Hathaway、C. W. Roberts

  DOI：10.1021/ja01597a052

  日期：1956.8