methyl 2-hydroxy-2-trifluoromethylpent-4-ynoate | 537034-30-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 2-hydroxy-2-trifluoromethylpent-4-ynoate
• 英文别名: 2-Hydroxy-2-trifluoromethyl-pent-4-ynoic acid methyl ester；methyl 2-hydroxy-2-(trifluoromethyl)pent-4-ynoate
• CAS: 537034-30-3
• 化学式: C₇H₇F₃O₃
• 分子量: 196.126
• InChiKey: LVSGOCLHIDWNST-UHFFFAOYSA-N

物化性质

• 沸点：
  282.0±40.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-hydroxy-2-trifluoromethylpent-4-ynoate 在 三乙胺 、 silver(l) oxide 作用下， 以 丙酮 为溶剂， 以55 %的产率得到
  参考文献：
  名称：

  [EN] HERBICIDAL ARYLDIHYDROFURANE CARBOXYLATES
  [FR] CARBOXYLATES D'ARYLDIHYDROFURANE HERBICIDES

  摘要：

  The invention relates to compounds of formula (I), and their use as herbicides. In said formula, R1to R10represent groups such as hydrogen, halo-gen or linear or cyclic organic groups such as alkyl, alkenyl, alkynyl, cycloalkyl, or alkoxy. The invention further refers to a composition comprising such compound and to the use thereof for controlling unwanted vegetation.

  公开号：

  WO2022268564A1
• 作为产物：
  描述：

  三氟丙酮酸甲酯 、 allenylmagnesium bromide 以 乙醚 为溶剂， 反应 2.5h， 以52%的产率得到methyl 2-hydroxy-2-trifluoromethylpent-4-ynoate
  参考文献：
  名称：

  Synthesis of furanyl- and triazolyl-containing α-CF3-α-hydroxy acids and their derivatives

  摘要：

  从三氟甲基丙二酸二乙酯出发，通过铜催化有机叠氮化物与含CF3取代的乙炔的[3+2]环加成反应，合成了α-CF3取代的α-甲氧基-α-(呋喃-2-基)乙酸及其衍生物，以及甲基α-CF3取代的α-羟基-β-(1,2,3-三唑基)丙酸酯。

  DOI：

  10.1007/s11172-020-2760-4

文献信息

• Facile synthesis of phosphorylated azides in ionic liquids and their use in the preparation of 1,2,3-triazoles
  作者：Oleg I. Artyushin、Daria V. Vorob'eva、Tamara P. Vasil'eva、Sergey N. Osipov、Gerd-Volker Röschenthaler、Irina L. Odinets

  DOI：10.1002/hc.20420

  日期：2008.4

  The facile general synthetic route to azidoalkylphosphonates by the nucleophilic substitution reaction in a series of bromoalkylphosphonates was elaborated, using 1-butyl-3-methylimidazolium hexafluorophosphate ([bmim][PF6]) as a recyclable reaction medium. These azidoalkylphosphonates were used as intermediates for copper(I)-catalyzed regioselective 1,3-dipolar cycloaddition with a variety of alkynes

  使用 1-丁基-3-甲基咪唑鎓六氟磷酸盐 ([bmim][PF6]) 作为可回收的反应介质，详细阐述了通过一系列溴代烷基膦酸酯的亲核取代反应合成叠氮烷基膦酸酯的简便通用途径。这些叠氮烷基膦酸酯被用作铜（I）催化的区域选择性 1,3-偶极环加成与各种炔烃的中间体，得到 4-取代的（1H-1,2,3-三唑-1-基）烷基膦酸酯作为潜在的候选药物. © 2008 Wiley Periodicals, Inc. 杂原子化学 19:293–300, 2008; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20420
• Synthesis of α-Trifluoromethyl-α-hydroxy Acid-Peptide Conjugates via Click Chemistry
  作者：Sergey Osipov、Valentine Nenajdenko、Nadezhda Sokolova、Daria Vorobyeva、Tamara Vasilyeva

  DOI：10.1055/s-0031-1289609

  日期：2012.1

  A simple and convenient method for the incorporation of fluorinated α-hydroxy acids into peptides is described. The target conjugates were obtained from α-alkynyl-α-trifluoromethyl-α-hydroxy acids and azido peptides via the copper(I)-catalyzed Huisgen cycloaddition reaction (click chemistry). After straightforward deprotection, the α-trifluoromethyl-α-hydroxy acid containing peptides may find important applications in biochemistry and medicinal chemistry.

  描述了一种简单且便利的方法，将氟化的α-羟基酸引入肽中。目标结合物是通过铜(I)催化的Huisgen环加成反应（点击化学）从α-炔基-α-三氟甲基-α-羟基酸和叠氮肽中获得的。经过简单去保护后，含有α-三氟甲基-α-羟基酸的肽可能在生物化学和药物化学中找到重要应用。
• Carbonyl-yne reactions of 3,3,3-trifluoropyruvates
  作者：Alexander S Golubev、Natalia N Sergeeva、Lothar Hennig、Alexey F Kolomiets、Klaus Burger

  DOI：10.1016/s0040-4020(03)00084-x

  日期：2003.2

  An efficient synthesis of trifluoromethyl-containing 2,3-allenols via carbonyl-yne reaction of 3,3,3-trifluoropyruvates with acetylenes is described. In the presence of MgBr2.Et2O the reaction of methyl trifluoropyruvate with hex-1-yne proceeds diastereoselectively. Trifluoromethyl-substituted 2,3-allenols can be stereoselectively transformed into trifluoromethyl-substituted 2,5-dihydrofurans on treatment with AgNO3. (C) 2003 Elsevier Science Ltd. All rights reserved.
• [EN] HERBICIDAL ARYLCYCLOPENTENE CARBOXAMIDES<br/>[FR] ARYLCYCLOPENTÈNE CARBOXAMIDES HERBICIDES
  申请人：[en]BASF SE

  公开号：WO2022268563A1

  公开（公告）日：2022-12-29

  The invention relates to compounds of formula (I), and their use as herbicides. In said formula, R1to R8represent groups such as hydrogen, halo-gen or organic groups such as alkyl, alkenyl, alkynyl, or alkoxy; W1and W2are -CR9R10-, -C(O)-, -O-, X is a bond or a divalent unit; Y is hydrogen, cyano, hydroxyl or a linear or cyclic organic group. The invention further refers to a composition comprising such compound and to the use thereof for controlling unwanted vegetation.