N-trifluoroacetyl-(S)-valine methyl ester | 1463-21-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-trifluoroacetyl-(S)-valine methyl ester
• 英文别名: N-trifluoroacetyl-L-valine methyl ester；N-Trifluoracetyl-L-valin-methylester；methyl (2S)-3-methyl-2-[(2,2,2-trifluoroacetyl)amino]butanoate
• CAS: 1463-21-4
• 化学式: C₈H₁₂F₃NO₃
• 分子量: 227.183
• InChiKey: KCASHPNYDVOBJR-YFKPBYRVSA-N

物化性质

• 沸点：
  233.9±40.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  N-trifluoroacetyl-(S)-valine methyl ester 在 肼 作用下， 生成 (S)-Val-NHNH₂
  参考文献：
  名称：

  Weygand,F.; Swodenk,W., Chemische Berichte, 1960, vol. 93, p. 1693 - 1696

  摘要：

  DOI：
• 作为产物：
  描述：

  (4S)-4-异丙基-5-氧代-1,3-恶唑烷-3-羧酸苄基酯 在 palladium on activated charcoal 盐酸 、 氢气 、 碳酸氢钠 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 反应 28.0h， 生成 N-trifluoroacetyl-(S)-valine methyl ester
  参考文献：
  名称：

  甲醇碳酸氢钠水溶液通过5-恶唑烷酮温和再生氨基酸烷基酯的羧基

  摘要：

  一种简单的无消旋方法使得可以通过中间体5-恶唑烷酮再生氨基酸烷基酯的羧酸基团，该中间体通过在甲醇水溶液中用碳酸氢钠处理而水解。

  DOI：

  10.1016/j.tetlet.2003.08.028

文献信息

• Enantioselective Cyclopropanation of Allylic Alcohols. The Effect of Zinc Iodide
  作者：Scott E. Denmark、Stephen P. O'Connor

  DOI：10.1021/jo9702397

  日期：1997.5.1

  catalytic, enantioselective cyclopropanation of allylic alcohols is examined with bis(iodomethyl)zinc as the reagent and bis-methanesulfonamide 7 as the catalyst. Significant rate enhancement was observed when 1 equiv of zinc iodide was present, but more importantly, the enantiomeric excess of the product cyclopropane increased from 80% to 89% for the substrate cinnamyl alcohol. Reaction studies and spectroscopic

  以双（碘甲基）锌为试剂，以双甲磺酰胺7为催化剂，研究了碘化锌对烯丙基醇催化，对映选择性环丙烷化的影响。当存在1当量的碘化锌时，观察到速率显着提高，但是更重要的是，底物肉桂醇的产物环丙烷的对映体过量从80％增加到89％。反应研究和光谱研究表明，这种显着影响是通过Schlenk平衡进行试剂修饰的结果，该平衡产生了更具反应性和选择性的碘化锌（碘甲基）。
• Structure and mechanism in aerobic alkene epoxidations promoted by ruthenium complexes of bis(dihydrooxazole) ligands
  作者：Simon Bennett、Stephen M. Brown、Gr�inne Conole、Margalith Kessler、Simon Rowling、Ekkehard Sinn、Simon Woodward

  DOI：10.1039/dt9950000367

  日期：——

  distorted and this is borne out by crystallographic comparison of the model complexes cis-[W(CO)4(S,S)-R2C([graphic omitted])2}](R = H or Me). Mechanistic studies of the epoxidation of styrene and stilbenes in the presence of isobutyraldehyde and molecular oxygen using the ruthenium complexes as catalysts in the presence and absence of 4-tert-butylcatechol as a radical trap revealed that the metals act

  [RuCl 2（NCMe）2（cod）]与双（二氢恶唑）反应，得到[RuCl 2（cod）（S，S）-R 1 2 C-（[省略图示]）2 }]（cod =环辛-1,5-二烯; R 1 = H，R 2 = CH 2的pH值或镨我; R 1 =我，R 2 = PR我）。苄基配合物已经在晶体学上进行了表征。六甲基取代的化合物的配合物的红外光谱表明，配体相对失真，这是通过模型配合物顺式的晶体学比较证实的。-[W（CO）4 （S，S）-R 2 C（[省略图形]）2 }]（R = H或Me）。在存在和不存在4-叔丁基邻苯二酚作为自由基捕集剂的情况下，使用钌配合物作为催化剂，在异丁醛和分子氧存在下，苯乙烯和苯乙烯的环氧化机理研究表明，金属可作为促进Pr生成的促进剂我CO 3 H和这进行环氧化，或者直接或者通过形成氧代-钌物种。
• Design, Synthesis, and Applications of Potential Substitutes of <i>t</i>-Bu-Phosphinooxazoline in Pd-Catalyzed Asymmetric Transformations and Their Use for the Improvement of the Enantioselectivity in the Pd-Catalyzed Allylation Reaction of Fluorinated Allyl Enol Carbonates
  作者：Étienne Bélanger、Marie-France Pouliot、Marc-André Courtemanche、Jean-François Paquin

  DOI：10.1021/jo2019653

  日期：2012.1.6

  substitutes of t-Bu-PHOX in asymmetric catalysis is reported. The design relies on the incorporation of geminal substituents at C5 in combination with a substituent at C4 other than t-butyl (i-Pr, i-Bu, or s-Bu). Most of these new members of the PHOX ligand family behave similarly in terms of stereoinduction to t-Bu-PHOX in three palladium-catalyzed asymmetric transformations. Electronically modified ligands

  报道了t -Bu-PHOX的潜在替代品在不对称催化中的设计，合成和应用。该设计依赖于在C5处引入双键取代基与在C4处而不是叔丁基（i- Pr，i- Bu或s- Bu）的取代基的结合。在三个钯催化的不对称转化中，PHOX配体家族的这些新成员中的大多数在立体诱导方面与t -Bu-PHOX相似。还制备了电子修饰的配体，并用于改善氟化烯丙基烯醇碳酸酯在钯催化的烯丙基化反应中的对映选择性。
• (S)-4-Isopropyl-5,5-dimethyl-1,3-oxazolidinethione as chiral auxiliary for the intramolecular sulfur transfer in α,β-unsaturated N-acylimides, promoted by NbCl5
  作者：Aurelio Ortiz、Leticia Quintero、Hector Hernández、Sotero Maldonado、Guadalupe Mendoza、Sylvain Bernès

  DOI：10.1016/s0040-4039(02)02837-x

  日期：2003.2

  The 1,3-oxazolidinethi one 4 has been synthesized from (S)-valine and used in the intramolecular sulfur transfer in its N-enoyl derivatives in the presence of NbCl5 as catalyst, which, moreover, works as an indicator of the course of the reaction. The adducts have subsequently been transformed into the corresponding beta-mercapto esters by action of Sm(OTf)(3) in methanol. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Cycloforskamide, a Cytotoxic Macrocyclic Peptide from the Sea Slug <i>Pleurobranchus forskalii</i>
  作者：Karen Co Tan、Toshiyuki Wakimoto、Kentaro Takada、Takashi Ohtsuki、Nahoko Uchiyama、Yukihiro Goda、Ikuro Abe

  DOI：10.1021/np400404r

  日期：2013.7.26

  A macrocylic dodecapeptide, cycloforskamide, was isolated from the sea slug Pleurobranchus forskalii, collected off Ishigaki Island, Japan. Its planar structure was deduced by extensive NMR analyses and was further confirmed by MS/MS fragmentation analyses. Finally, the absolute configuration was determined by total hydrolysis and chiral-phase gas chromatographic analysis. This novel dodecapeptide contains three D-amino acids and three thiazoline heterocycles and exhibits cytotoxicity against murine leukemia P388 cells, with an IC50 of 5.8 mu M.