2,2,2-trifluoroethyl picolinate | 93111-30-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,2,2-trifluoroethyl picolinate
• 英文别名: 2,2,2-Trifluoroethyl pyridine-2-carboxylate
• CAS: 93111-30-9
• 化学式: C₈H₆F₃NO₂
• 分子量: 205.136
• InChiKey: HSXJLYTYCAXXPR-UHFFFAOYSA-N

物化性质

• 沸点：
  226.1±40.0 °C(Predicted)
• 密度：
  1.336±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  39.2
• 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 picolinate 在 水 、 铜 作用下， 生成 2-吡啶甲酸 、 2,2,2-三氟乙醇
  参考文献：
  名称：

  Leaving group effect in the cleavage of picolinate esters catalyzed by hydroxy-functionalized metallomicelles

  摘要：

  Micellar aggregates of complexes of transition metal ions with the hydroxy-functionalized surfactant 1a are very effective catalysts of the cleavage of activated esters of alpha-amino acids. To ascertain their effectiveness toward unactivated esters, a systematic kinetic study was undertaken employing as substrates the picolinic acid esters 3a-1, the pK(a) of their alcoholic portion spanning more than 12 units from 3.6 to 16. The leaving group effect was investigated in water, pH=6.3, in the absence and presence of CU2+ ions, in the presence of the nonmicellar complex 2-CU2+, and in the presence of micellar aggregates made of 1a-Cu2+ or of its O-methylated analog 1b-Cu2+. In the presence of free metal ions the leaving group effect is negligible in the case of esters with good leaving groups (pK(a)

  DOI：

  10.1021/jo00080a006
• 作为产物：
  描述：

  2-吡啶甲酸 、 2,2,2-三氟乙醇 在 二乙胺基三氟化硫 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以75%的产率得到2,2,2-trifluoroethyl picolinate
  参考文献：
  名称：

  XtalFluor-E介导的全氟化醇直接酯化羧酸

  摘要：

  据报道，由XtalFluor-E介导的羧酸与全氟化醇直接酯化。仅使用稍微过量的（2当量）全氟化醇，就可以以中等到极高的收率，用宽范围的羧酸（包括芳族，杂芳族，脂族和非外消旋手性底物）获得相应的多氟化酯。对照实验表明，该反应不通过的酰基氟化物的形成继续进行，但最有可能通过一个（二乙基氨基）二氟- λ 4硫烷基羧酸盐中间体。

  DOI：

  10.1021/acs.orglett.6b03365

文献信息

• Metal-free transesterification catalyzed by tetramethylammonium methyl carbonate
  作者：Manabu Hatano、Yuji Tabata、Yurika Yoshida、Kohei Toh、Kenji Yamashita、Yoshihiro Ogura、Kazuaki Ishihara

  DOI：10.1039/c7gc03858e

  日期：——

  tetramethylammonium methyl carbonate is effective as a catalyst for the chemoselective, scalable, and reusable transesterification of various esters and alcohols in common organic solvents. In situ-generated highly active species, tetramethylammonium alkoxides, can greatly avoid self-decomposition at ≤110 °C, and are reusable. In particular, chelating substrates, such as amino alcohols, diols, triols,

  不含环境的无金属碳酸四甲基铵甲酯可有效用作各种酯和醇在普通有机溶剂中的化学选择性，可扩展性和可重复使用的酯交换反应的催化剂。原位生成的高活性物质四甲基铵醇盐可大大避免在≤110°C时自分解，并可重复使用。特别地，可以使用使常规金属盐催化剂失活的螯合底物，例如氨基醇，二醇，三醇，糖衍生物，生物碱，α-氨基酸酯等。还展示了100克规模的生物柴油生产。
• Divalent metal ion catalysis in the hydrolysis of esters of picolinic acid. Metal ion promoted hydroxide ion and water catalyzed reactions
  作者：Thomas H. Fife、Theodore J. Przystas

  DOI：10.1021/ja00290a048

  日期：1985.2
• [EN] METHODS FOR PREPARING DOXORUBICIN DERIVATIVES<br/>[FR] PROCEDES PERMETTANT DE PREPARER DES DERIVES DE DOXORUBICINE
  申请人：ALBANY MOLECULAR RES INC

  公开号：WO2003057687A1

  公开（公告）日：2003-07-17

  The present invetion relates to a process for preparation of a product compound of formula (I), where R1 is an acyl group. The process involves reacting a starting compound of formula (II), with an activated acyl donor compound in the presence of a non-chemically modified lipase, under conditions effective to produce the product compound.
• [EN] METHODS FOR PREPARING ANTHRACYCLINONE DERIVATIVES AND ANTHRACYCLINONE DERIVATIVES PER SE<br/>[FR] METHODES PERMETTANT DE PREPARER DES DERIVES D'ANTHRACYCLINONE ET LESDITS DERIVES D'ANTHRACYCLINONE
  申请人：ALBANY MOLECULAR RES INC

  公开号：WO2003057896A1

  公开（公告）日：2003-07-17

  The present invention relates to a process for preparation of a product compound of the Formula (I), where R1 is an acyl group, R2 is H, an N-alkylated amino sugar, or a non-basic sugar moiety, and R3 is H, OH, or OCH3. The process involves reacting a starting compound of the Formula (II) with an acyl donor compound in the presence of a non-chemically modified lipase, under conditions effective to produce the product compound. Another aspect of the present invention relates to a compound of the following Formula (III), where: R1 is an acyl radical of a carboxylic acid selected from the group consisting of: polyethylene glycol acetic acid and polyunsaturated fatty acid; and R2 = 2,6-dideoxy-2-fluoro-α-talopyranosyl; 3-trifluoroacetylamino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl; or 3-deamino-3-(2'-pyrroline-1'-yl)-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl; or a pharmaceutically acceptable salt thereof. The present invention also relates to a compound of the Formula (IV) where n is 4 or 5, or a pharmaceutically acceptable salt thereof. Another aspect of the present invention relates to a compound of the Formula (V) where: R1 is an acyl group, R2 is 3-substituted allyloxycarbonylamino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl, R3 is H, OH, or OCH3.
• [EN] BIOCATALYTIC PROCESS FOR PREPARING ENANTIOMERICALLY ENRICHED PRAMIPEXOLE<br/>[FR] PROCEDE BIOCATALYTIQUE DE FABRICATION DE PRAMIPEXOLE ENRICHI ENANTIOMERIQUEMENT
  申请人：AMR TECHNOLOGY INC

  公开号：WO2006012277A2

  公开（公告）日：2006-02-02

  biocatalytic process for preparing enantiomerically enriched pramipexole and pramipexole precursors are disclosed.