3,4,6-trifluoro-5-hydroxyphthalic acid | 28749-88-4

• 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: 3,4,6-trifluoro-5-hydroxyphthalic acid
• 英文别名: 4-hydroxy-3,5,6-trifluorophthalic acid
• CAS: 28749-88-4
• 化学式: C₈H₃F₃O₅
• 分子量: 236.104
• InChiKey: BYXIMXYJZPMWAX-UHFFFAOYSA-N

物化性质

• 熔点：
  171-172 °C
• 沸点：
  394.7±42.0 °C(Predicted)
• 密度：
  1.880±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,4,6-trifluoro-5-hydroxyphthalic acid 在 硫酸 、 水 、 potassium carbonate 、 三氟乙酸酐 、 potassium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.5h， 生成 4-benzyloxy-3,5,6-trifluorophthalic anhydride
  参考文献：
  名称：

  聚合物负载的手性氟化二氢吡啶鎓（II）配合物，用于甲硅烷基烯醇醚的不对称胺化

  摘要：

  四（N-四氟邻苯二甲酰基- （S）-叔亮氨酸酯] [Rh 2（S -TFPTTL）4 ]的四氢吡啶鎓（II）的固定化是通过将含二氢吡啶鎓（II）配合物的单体与苯乙烯共聚完成的。和1,6-双（4-乙烯基苄氧基）己烷作为柔性交联剂。聚合物负载的手性氟化二氢吡啶鎓（II）配合物催化甲硅烷基烯醇醚与[ N-（2-硝基苯基磺酰基）亚氨基]苯基碘丁烷（NsNIPh）的胺化反应，以高收率和高对映选择性提供α-氨基酮。在固体反应物的存在下，催化剂的使用量高达20倍，很容易经受住搅拌。

  DOI：

  10.1002/adsc.201200219
• 作为产物：
  描述：

  3,4,5,6-四氟邻苯二腈 在 sodium hydroxide 、 锌 作用下， 生成 3,4,6-trifluoro-5-hydroxyphthalic acid
  参考文献：
  名称：

  Process Improvements in the Synthesis of 2,4,5-Trifluorobenzoic Acid. Selective Hydrodefluorination of Tetrafluorophthalimides

  摘要：

  An improved preparation of the fluoroquinolone antibacterial intermediate 2,4,5-trifluorobenzoic acid is described. A combination of a selective hydrodefluorination and hydrolysis reaction of 3,4,5,6-tetrafluoro-N-methylphthalimide leading to 3,5,6-trifluorophthalic acid was key to the success of the profess. In addition the development of a two-step, one-pot imidization/halogen exchange from tetrachlorophthalic anhydride to 3,4,5,6-tetrafluoro-N-methylphthalimide in sulfolane solvent is detailed.

  DOI：

  10.1021/op970244c

文献信息

• TAU-PROTEIN TARGETING PROTACS AND ASSOCIATED METHODS OF USE
  申请人：Arvinas, Inc.

  公开号：US20180125821A1

  公开（公告）日：2018-05-10

  The present disclosure relates to bifunctional compounds, which find utility as modulators of tau protein. In particular, the present disclosure is directed to bifunctional compounds, which contain on one end a VHL or cereblon ligand which binds to the E3 ubiquitin ligase and on the other end a moiety which binds tau protein, such that tau protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of tau. The present disclosure exhibits a broad range of pharmacological activities associated with degradation/inhibition of tau protein. Diseases or disorders that result from aggregation or accumulation of tau protein are treated or prevented with compounds and compositions of the present disclosure.

  本公开涉及双功能化合物，其作为tau蛋白的调节剂具有实用性。具体而言，本公开涉及含有一端结合到E3泛素连接酶的VHL或cereblon配体，另一端结合到tau蛋白的双功能化合物，使得tau蛋白与泛素连接酶靠近，以实现tau蛋白的降解（和抑制）。本公开展示了与tau蛋白降解/抑制相关的广泛药理活性。本公开的化合物和组合物用于治疗或预防由tau蛋白聚集或积累导致的疾病或紊乱。
• Trifluorohydroxyaromatic acid and preparation thereof
  申请人：UBE Industries, Ltd.

  公开号：US04831190A1

  公开（公告）日：1989-05-16

  There are disclosed 2,4,5-Trifluoro-3-hydroxybenzoic acid represented by the following formula (I): ##STR1## and a salt thereof and a process for preparing the same. Further, there is disclosed a process for preparing 3,5,6-trifluoro-4-hydroxyphthalic acid, which is employed for preparing the above compound.

  本发明公开了以下公式（I）所代表的2,4,5-三氟-3-羟基苯甲酸：##STR1##及其盐和制备该化合物的方法。此外，本发明还公开了制备3,5,6-三氟-4-羟基邻苯二甲酸的方法，该方法用于制备上述化合物。
• Development of Tubulin-Polymerization Inhibitors Based on the Thalidomide Skeleton
  作者：Hiroshi Aoyama、Tomomi Noguchi、Takashi Misawa、Takanori Nakamura、Hiroyuki Miyachi、Yuichi Hashimoto、Hisayoshi Kobayashi

  DOI：10.1248/cpb.55.944

  日期：——

  We synthesized a series of compounds based on the potent tubulin-polymerization inhibitor 5-hydroxy-2-(2,6-diisopropylphenyl)-1H-isoindole-1,3-dione [5HPP-33 (3)], which is structurally derived from thalidomide (1), and investigated their inhibitory effects on tubulin polymerization. Direct interaction between 5HPP-33 (3) and α,β-tubulin heterodimer protein was demonstrated by means of a surface plasmon resonance study.

  我们合成了一系列化合物，这些化合物基于强效微管蛋白聚合抑制剂5-羟基-2-(2,6-二异丙基苯基)-1H-异吲哚-1,3-二酮[5HPP-33 (3)]，该化合物在结构上源自沙利度胺(1)，我们研究了它们对微管蛋白聚合的抑制作用。通过表面等离子共振研究，证明了5HPP-33 (3)与α,β-微管蛋白异二聚体之间的直接相互作用。
• Process for the preparation of esters of aromatic carboxylic acids
  申请人：Hoechst Aktiengesellschaft

  公开号：US05744628A1

  公开（公告）日：1998-04-28

  The present invention relates to a process for the preparation of compounds of the formula (1) R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 ArCOOR (1) in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are hydrogen, a halogen, an alkyl or alkoxy group having 1 to 6 carbon atoms, OR, NHR, NR.sub.2, SR or COOR, R being an alkyl radical having 1 to 4 carbon atoms, Ar is an aryl radical having 6 to 12 carbon atoms and the radical R identified in formula (1) has the above meaning, by reacting a compound of the formula (2) R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 ArCOOH (2) in which R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are identical or different and are hydrogen, a halogen, an alkyl or alkoxy group having 1 to 6 carbon atoms, OH, NH.sub.2, NHR, SH or COOH and Ar has the same meaning as in formula (1), with a sulfate of the formula (RO).sub.2 SO.sub.2, in which R has the above meaning, at a pH from 5 to 12 in the presence of a water-insoluble tertiary amine and water at a temperature from 10.degree. to 120.degree. C. in the presence or absence of a water-insoluble solvent and with addition of a base.

  本发明涉及一种制备式（1）R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 ArCOOR（1）化合物的方法，其中R.sup.1，R.sup.2，R.sup.3，R.sup.4和R.sup.5相同或不同，分别为氢，卤素，具有1至6个碳原子的烷基或烷氧基，OR，NHR，NR.sub.2，SR或COOR，其中R为具有1至4个碳原子的烷基基团，Ar为具有6至12个碳原子的芳基基团，式（1）中所识别的基团R具有上述含义，通过将式（2）R.sup.1 R.sup.2 R.sup.3 R.sup.4 R.sup.5 ArCOOH（2）化合物与式（RO）.sub.2 SO.sub.2的硫酸盐在水不溶性三级胺和水的存在下，在pH为5至12的温度为10℃至120℃的条件下，加入水不溶性溶剂和碱，反应制备而得。其中R.sup.1，R.sup.2，R.sup.3，R.sup.4和R.sup.5相同或不同，分别为氢，卤素，具有1至6个碳原子的烷基或烷氧基，OH，NH.sub.2，NHR，SH或COOH，Ar与式（1）中相同。
• 4-oxoquinoline-3-carboxylic acid derivatives and their use
  申请人：Sankyo Company Limited

  公开号：US05073556A1

  公开（公告）日：1991-12-17

  Compounds of formula (I): ##STR1## (in which: R.sup.1 represents fluorinated methoxy; R.sup.2 represents a nitrogen-containing heterocyclic group and R.sup.3 represents hydrogen or amino) and pharmaceutically acceptable salts, esters and amides thereof are valuable antibacterial agents, which may be prepared by reacting a compound similar to that of formula (I) but in which R.sup.2 is replaced by a halogen atom with a compound providing the required group R.sup.2.

  化合物的公式 (I): ##STR1##(其中: R.sup.1代表氟代甲氧基; R.sup.2代表含氮杂环基团，R.sup.3代表氢或氨基)以及其药学上可接受的盐、酯和酰胺是有价值的抗菌剂，可以通过将类似于公式 (I)中R.sup.2被卤素原子取代的化合物与提供所需的R.sup.2基团的化合物反应而制备得到。