2,2,2-trifluoroethyl glyoxalate | 172332-66-0

• 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: 2,2,2-trifluoroethyl glyoxalate
• 英文别名: 2,2,2-trifluoroethyl glyoxylate；Trifluoroethyl glyoxylate；Acetic acid, oxo-, 2,2,2-trifluoroethyl ester；2,2,2-trifluoroethyl 2-oxoacetate
• CAS: 172332-66-0
• 化学式: C₄H₃F₃O₃
• 分子量: 156.061
• InChiKey: XUMYJAUXFXFRNF-UHFFFAOYSA-N

物化性质

• 沸点：
  107.9±50.0 °C(Predicted)
• 密度：
  1.396±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2,2-trifluoroethyl glyoxalate 、 1-三苯基膦-2-丙酮 以 苯 为溶剂， 反应 0.5h， 以46%的产率得到2,2,2-trifluoroethyl-(E)-4-oxopent-2-enoate
  参考文献：
  名称：

  （E）-4-Oxopent-2-enoates的催化和对映选择性Diels-Alder反应

  摘要：

  被强酸三氟甲磺酸酯或AlBr 3活化的新型恶唑硼烷形成阳离子手性催化剂。这些是高度有效的区域和对映选择性Diels-Alder反应的有效催化剂，使用取代的（E）-4-氧opent-2-烯酸酯作为亲二烯体。

  DOI：

  10.1021/acs.orglett.7b01692
• 作为产物：
  描述：

  di-(2,2,2-trifluoroethyl) tartrate 在 过碘酸 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 2,2,2-trifluoroethyl glyoxalate
  参考文献：
  名称：

  Superoxide dismutase mimetics. Part 2: synthesis and structure–Activity relationship of glyoxylate- and glyoxamide-Derived metalloporphyrins

  摘要：

  Novel glyoxylate- and glyoxamide-derived metalloporphyrins 26-58 were synthesized and evaluated as potential superoxide dismutase (SOD) mimetics. Relative to previously studied MnTBAP analogues, the glyoxylate-derived metalloporphyrins 32, 39, and 54 and glyoxamide-derived metalloporphyrin 49, exhibited enhanced activity in the SOD assay and the majority of the analogues in the current series showed enhanced inhibition of lipid peroxidation and catalase activity. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00272-4

文献信息

• Periselective and enantioselective carbonyl–ene reaction of isoprene with fluoroalkyl glyoxylate catalysed by modified binaphthol–titanium complex: asymmetric catalytic synthesis of enantiomerically pure ipsdienol
  作者：Masahiro Terada、Koichi Mikami

  DOI：10.1039/c39950002391

  日期：——

  The asymmetric reaction of trifluoroethyl glyoxylate 3d with isoprene 4 catalysed by the modified binaphthol–titanium complex 2b provides the ene product 5d in high periselectivity (92%) and complete enantioselectivity, which can be converted to ipsdienol 1, a component of the aggregation pheromone of the bark beetle, genus lps, in enantiomerically pure form.

  三氟乙基乙醇酸酯3d与异戊二烯4在改性联萘酚钛络合物2b催化下发生的不对称反应，以92%的高产率和完全的立体选择性提供了ene产物5d，该产物可以转化为纯对映体形式的ipsdienol 1，即树皮甲虫（lps属）聚集信息素的一个组分。
• A Multistage, One-Pot Procedure Mediated by a Single Catalyst:  A New Approach to the Catalytic Asymmetric Synthesis of β-Amino Acids
  作者：Ahmed M. Hafez、Travis Dudding、Ty R. Wagerle、Meha H. Shah、Andrew E. Taggi、Thomas Lectka

  DOI：10.1021/jo034150e

  日期：2003.7.1

  A catalytic asymmetric procedure for the preparation of beta-amino acids (specifically beta-substituted aspartic acid derivatives) is reported. The cinchona alkaloid catalyst benzoylquinine (BQ) mediates up to five distinct steps of a reaction pathway, all in one reaction vessel. The products of this reaction, highly optically enriched beta-substituted aspartic acid derivatives, were prepared from

  报道了用于制备β-氨基酸（特别是β-取代的天冬氨酸衍生物）的催化不对称方法。金鸡纳生物碱催化剂苯甲酰基奎宁（BQ）最多可在一个反应​​容器中介导反应路径的五个不同步骤。该反应的产物，高度光学富集的β-取代的天冬氨酸衍生物，是在催化剂存在下由N-酰基-α-氯甘氨酸酯和酰氯制备的。该方法也适用于合成含有β-取代的天冬氨酸单元的小多肽，包括抗生素溶菌素的非天然片段。发现向该系统中添加路易斯酸可加快反应路径中特定步骤的速率。这种反应的机理方面，
• Substituted porphyrins
  申请人：Duke University

  公开号：US06479477B1

  公开（公告）日：2002-11-12

  The present invention relates, in general, to a method of modulating physiological and pathological processes and, in particular, to a method of modulating cellular levels of oxidants and thereby processes in which such oxidants are a participant. The invention also relates to compounds and compositions suitable for use in such methods. Compounds of the invention include those of Formula I.

  本发明涉及一种调节生理和病理过程的方法，特别是一种调节细胞氧化剂水平及其参与的过程的方法。本发明还涉及适用于这种方法的化合物和组合物。本发明的化合物包括公式I中的化合物。
• Superoxide dismutase mimetics. Part 2: synthesis and structure–Activity relationship of glyoxylate- and glyoxamide-Derived metalloporphyrins
  作者：Michael P Trova、Polivina Jolicia F Gauuan、Anthony D Pechulis、Stephen M Bubb、Stephen B Bocckino、James D Crapo、Brian J Day

  DOI：10.1016/s0968-0896(03)00272-4

  日期：2003.7

  Novel glyoxylate- and glyoxamide-derived metalloporphyrins 26-58 were synthesized and evaluated as potential superoxide dismutase (SOD) mimetics. Relative to previously studied MnTBAP analogues, the glyoxylate-derived metalloporphyrins 32, 39, and 54 and glyoxamide-derived metalloporphyrin 49, exhibited enhanced activity in the SOD assay and the majority of the analogues in the current series showed enhanced inhibition of lipid peroxidation and catalase activity. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Catalytic and Enantioselective Diels–Alder Reactions of (<i>E</i>)-4-Oxopent-2-enoates
  作者：Su-Lei Zhang、Yong Lu、Yuan-He Li、Kuang-Yu Wang、Jia-Hua Chen、Zhen Yang

  DOI：10.1021/acs.orglett.7b01692

  日期：2017.8.4

  Novel oxazaborolidines activated by the strong acid triflimide or AlBr3 form cationic chiral catalysts. These are effective catalysts for highly regio- and enantioselective Diels–Alder reactions using substituted (E)-4-oxopent-2-enoates as dienophiles.

  被强酸三氟甲磺酸酯或AlBr 3活化的新型恶唑硼烷形成阳离子手性催化剂。这些是高度有效的区域和对映选择性Diels-Alder反应的有效催化剂，使用取代的（E）-4-氧opent-2-烯酸酯作为亲二烯体。