2-(Tert-butoxycarbonylamino)-4-(trifluoromethyl)benzoic acid | 141940-28-5

• 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: 2-(Tert-butoxycarbonylamino)-4-(trifluoromethyl)benzoic acid
• 英文别名: 2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-(trifluoromethyl)benzoic acid
• CAS: 141940-28-5
• 化学式: C₁₃H₁₄F₃NO₄
• 分子量: 305.254
• InChiKey: LAXIZJYUJKOGPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(Tert-butoxycarbonylamino)-4-(trifluoromethyl)benzoic acid 在 2-氯-1-甲基吡啶碘化物 、 盐酸 作用下， 以 乙腈 、 水 为溶剂， 反应 0.17h， 生成 7-(三氟甲基)-1H-苯并[d][1,3]噁嗪-2,4-二酮
  参考文献：
  名称：

  A phosgene and peroxide-free one-pot tandem synthesis of isatoic anhydrides involving anthranilic acid, Boc anhydride, and 2-chloro-N-methyl pyridinium iodide

  摘要：

  A phosgene and peroxide-free approach for the synthesis of isatoic anhydrides has been described. The synthesis involves the carbamate formation with Boc anhydride followed by in situ cyclization to afford the isatoic anhydride. The importance of this synthetic strategy is in the ease of operation, scalability, and preparation from readily available raw materials. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.10.034
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 仲丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 20.5h， 生成 2-(Tert-butoxycarbonylamino)-4-(trifluoromethyl)benzoic acid
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New 1,2-Dihydro-4-hydroxy-2-oxo-3-quinolinecarboxamides for Treatment of Autoimmune Disorders:  Structure−Activity Relationship

  摘要：

  Roquinimex-related 3-quinolinecarboxamide derivatives were prepared and evaluated for treatment of autoimmune disorders. The compounds were tested in mice for their inhibitory effects on disease development in the acute experimental autoimmune encephalomyelitis model and selected compounds in the beagle dog for induction of proinflammatory reaction. Structure-activity relationships are discussed. Compound 8c, laquinimod, showed improved potency and superior toxicological profile compared to the lead compound roquinimex (1b, Linomide) and was selected for clinical studies (currently in phase II).

  DOI：

  10.1021/jm031044w

文献信息

• Novel Heterocyclidene Acetamide Derivative
  申请人：Uchida Hideharu

  公开号：US20080287428A1

  公开（公告）日：2008-11-20

  A compound represented by formula (I′): (wherein m, n, and p each represent 0 to 2; q represents 0 or 1; R 1 represents halogen, a hydrocarbon group, a heterocyclic group, an alkoxy group, an alkoxycarbonyl group, a sulfamoyl group, a CN group, an NO 2 group, or the like; R 2 represents halogen, amino, a hydrocarbon group, an aromatic heterocyclic group, or an oxo group; X 1 represents O, —NR 3 —, or —S(O)r-; X 2 represents a methylene group, O, —NR 3 —, or —S(O)r-; Q′ represents a heteroaryl group, a heteroarylalkyl group, a substituted aryl group, or an aralkyl group; Cycle moiety represents an aryl ring or a heteroaryl ring; and the wavy line represents an E-isomer or a Z-isomer), a salt of the compound, or a solvate of the compound or the salt. A pharmaceutical composition and a transient receptor potential type I (TRPV1) receptor antagonist each contain, as an active ingredient, at least one of the compound, a salt of the compound, and a solvate of the compound or the salt.

  一个由式(I′)表示的化合物：（其中m、n和p分别表示0到2；q表示0或1；R1表示卤素、烃基、杂环基、烷氧基、烷氧羰基、磺酰胺基、CN基团、NO2基团等；R2表示卤素、氨基、烃基、芳香杂环基或醛基；X1表示O、—NR3—或—S(O)r-；X2表示亚甲基、O、—NR3—或—S(O)r-；Q′表示异芳基基团、异芳基烷基基团、取代芳基基团或芳基烷基基团；Cycle moiety代表芳基环或杂芳基环；波浪线表示E异构体或Z异构体），该化合物的盐，或该化合物或其盐的溶剂络合物。一种药物组合物和一种瞬时受体电位类型I（TRPV1）受体拮抗剂，每种包含至少一种该化合物、该化合物的盐，或该化合物或其盐的溶剂络合物作为活性成分。
• NOVEL HETEROCYCLIDENE ACETAMIDE DERIVATIVE
  申请人：MOCHIDA PHARMACEUTICAL CO., LTD.

  公开号：EP1908753A1

  公开（公告）日：2008-04-09

  A compound represented by formula (I'): (wherein m, n, and p each represent 0 to 2; q represents 0 or 1; R1 represents halogen, a hydrocarbon group, a heterocyclic group, an alkoxy group, an alkoxycarbonyl group, a sulfamoyl group, a CN group, an NO2 group, or the like; R2 represents halogen, amino, a hydrocarbon group, an aromatic heterocyclic group, or an oxo group; X1 represents O, -NR3-, or -S(O)r-; X2 represents a methylene group, O, -NR3-, or - S(O)r-; Q' represents a heteroaryl group, a heteroarylalkyl group, a substituted aryl group, or an aralkyl group; Cycle moiety represents an aryl ring or a heteroaryl ring; and the wavy line represents an E-isomer or a Z-isomer), a salt of the compound, or a solvate of the compound or the salt. A pharmaceutical composition and a transient receptor potential type I (TRPV1) receptor antagonist each contain, as an active ingredient, at least one of the compound, a salt of the compound, and a solvate of the compound or the salt.

  式 (I') 所代表的化合物： (其中 m、n 和 p 分别代表 0 至 2；q 代表 0 或 1；R1 代表卤素、烃基、杂环基、烷氧基、烷氧羰基、氨基磺酰基、CN 基、NO2 基或类似基团；R2 代表卤素、氨基、烃基、芳香杂环基或氧代基团；X1 代表 O、-NR3- 或 -S(O)r- ；X2代表亚甲基、O、-NR3-或-S(O)r-； Q'代表杂芳基、杂芳烷基、取代芳基或芳烷基；循环分子代表芳基环或杂芳环；波浪线代表E-异构体或Z-异构体）、化合物的盐、或化合物或盐的溶液。一种药物组合物和一种瞬时受体电位Ⅰ型（TRPV1）受体拮抗剂各自含有至少一种化合物、化合物的盐和化合物或盐的溶液作为活性成分。
• US8383839B2
  申请人：——

  公开号：US8383839B2

  公开（公告）日：2013-02-26
• A phosgene and peroxide-free one-pot tandem synthesis of isatoic anhydrides involving anthranilic acid, Boc anhydride, and 2-chloro-N-methyl pyridinium iodide
  作者：Chhaya Verma、Somesh Sharma、Arunendra Pathak

  DOI：10.1016/j.tetlet.2013.10.034

  日期：2013.12

  A phosgene and peroxide-free approach for the synthesis of isatoic anhydrides has been described. The synthesis involves the carbamate formation with Boc anhydride followed by in situ cyclization to afford the isatoic anhydride. The importance of this synthetic strategy is in the ease of operation, scalability, and preparation from readily available raw materials. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis and Biological Evaluation of New 1,2-Dihydro-4-hydroxy-2-oxo-3-quinolinecarboxamides for Treatment of Autoimmune Disorders:  Structure−Activity Relationship
  作者：Stig Jönsson、Gunnar Andersson、Tomas Fex、Tomas Fristedt、Gunnar Hedlund、Karl Jansson、Lisbeth Abramo、Ingela Fritzson、Olga Pekarski、Anna Runström、Helena Sandin、Ingela Thuvesson、Anders Björk

  DOI：10.1021/jm031044w

  日期：2004.4.1

  Roquinimex-related 3-quinolinecarboxamide derivatives were prepared and evaluated for treatment of autoimmune disorders. The compounds were tested in mice for their inhibitory effects on disease development in the acute experimental autoimmune encephalomyelitis model and selected compounds in the beagle dog for induction of proinflammatory reaction. Structure-activity relationships are discussed. Compound 8c, laquinimod, showed improved potency and superior toxicological profile compared to the lead compound roquinimex (1b, Linomide) and was selected for clinical studies (currently in phase II).