4-Benzyl-4-(trifluoromethyl)-1,3-oxazolidine-2,5-dione | 139520-49-3

• 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: 4-Benzyl-4-(trifluoromethyl)-1,3-oxazolidine-2,5-dione
• CAS: 139520-49-3
• 化学式: C₁₁H₈F₃NO₃
• 分子量: 259.185
• InChiKey: SIQVJKDUMJYORK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-Benzyl-4-(trifluoromethyl)-1,3-oxazolidine-2,5-dione 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 12.0h， 生成 (S)-<2-(Trifluormethyl)phenylalanyl>(azaglycyl)alanin-ethylester
  参考文献：
  名称：

  Burger, Klaus; Schierlinger, Christian; Muetze, Kerstin, Liebigs Annalen der Chemie, 1994, # 4, p. 407 - 414

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(benzyloxycarbonyl)-α-(trifluoromethyl)phenylalanine 在 氯化亚砜 作用下， 以34%的产率得到4-Benzyl-4-(trifluoromethyl)-1,3-oxazolidine-2,5-dione
  参考文献：
  名称：

  通过4-三氟甲基-1,3-恶唑烷定-2,5-二酮引入α-三氟甲基α-氨基酸来修饰肽

  摘要：

  可以通过Leuchs酸酐将α-三氟甲基取代的α-氨基酸引入在羧基活化的肽的N-末端位置。

  DOI：

  10.1016/0040-4039(92)88047-9

文献信息

• Incorporation of the Unusual C^α-Fluoroalkylamino Acids into Cyclopeptides:  Synthesis of Arginine−Glycine−Aspartate (RGD) Analogues and Study of Their Conformational and Biological Behavior
  作者：Alma Dal Pozzo、Minghong Ni、Laura Muzi、Roberto de Castiglione、Rosanna Mondelli、Stefania Mazzini、Sergio Penco、Claudio Pisano、Massimo Castorina、Giuseppe Giannini

  DOI：10.1021/jm0511334

  日期：2006.3.1

  A series of six arginine-glycine-aspartate (RGD) cyclopeptide analogues containing a C-alpha-di- or trifluoromethylamino acid (alpha-Dfm or alpha-TfmAaa) at different positions of the ring were synthesized. All peptides were obtained in two diastereomeric forms, which were separated by HPLC. In vitro biological tests of the new cyclopeptides P were carried out in comparison with their corresponding cyclopeptides R lacking the alpha-fluoromethyl group. Five out of the six compounds P-I (containing (S)-alpha-Tfm-Aaa) showed activities in the nanomolar range, while the P-II compounds (containing (R)-a-Tfm-Aaa) were much less active or totally inactive. Only cyclo[RGDf-(S)-alpha TfmV] (P1-I) was found to be significantly more active than its model compound cyclo(RGDfV) (R1). The three-dimensional structure in water and DMSO was determined by NMR techniques and molecular dynamics (MD) calculations, but it was not possible to highlight significant differences in the backbone conformation of the peptides examined. Significant interproton distances, derived from nuclear Overhauser effect (NOE) experiments, were used to determine the absolute configuration of the side chains.
• Burger, Klaus; Schierlinger, Christian; Muetze, Kerstin, Liebigs Annalen der Chemie, 1994, # 4, p. 407 - 414
  作者：Burger, Klaus、Schierlinger, Christian、Muetze, Kerstin、Hollweck, Wolfgang、Koksch, Beate

  DOI：——

  日期：——
• Peptide modification by introduction of α-trifluoromethyl α-amino acids via 4-trifluoromethyl-1,3-oxazolidin-2,5-diones
  作者：Christian Schierlinger、Klaus Burger

  DOI：10.1016/0040-4039(92)88047-9

  日期：1992.1

  α-Trifluoromethyl substituted α-amino acids can be introduced into the N-terminal position of peptides on carboxyl group activation via Leuchs anhydrides.

  可以通过Leuchs酸酐将α-三氟甲基取代的α-氨基酸引入在羧基活化的肽的N-末端位置。