4-甲基-3-呋喃甲酸 | 101870-15-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 中文名称: 4-甲基-3-呋喃甲酸
• 中文别名: 4-甲基-3-呋喃羧酸
• 英文名称: 4-methyl-3-furancarboxylic acid
• 英文别名: 4-methylfuran-3-carboxylic acid
• CAS: 101870-15-9
• 化学式: C₆H₆O₃
• mdl: MFCD15143778
• 分子量: 126.112
• InChiKey: XOEFJYKFWPVPNZ-UHFFFAOYSA-N

物化性质

• 熔点：
  138-139 °C
• 沸点：
  234.3±20.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-甲基-3-呋喃甲酸 在 咪唑 、 4-二甲氨基吡啶 、 lithium hydroxide 、 diethylphosphoryl cyanide 、 氧气 、 rose bengal 、 三乙胺 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 pyridinium chlorochromate 、 (S)-2-甲基-CBS-恶唑硼烷 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 63.33h， 生成 (R)-3-(Diethyl-isopropyl-silanyloxy)-3-(4-methyl-2,5-dioxo-2,5-dihydro-furan-3-yl)-propionic acid benzyl ester
  参考文献：
  名称：

  （+）-互变霉素的全合成

  摘要：

  会聚立体控制（+）的总合成- tautomycin（1），蛋白质的特异性抑制剂丝氨酸/苏氨酸磷酸酶，已经通过C的酯化实现1. -C 7片段A' 7 4与C 1 - ç 26片段B' 7 6通过改进的山口方法和C的醛醇缩合反应17 -C 26片段C 5与C 1 -C 16片段d 6使用LDA作为关键步骤。片段5和6 分别以立体声控制的方式构造。

  DOI：

  10.1016/0040-4020(96)00811-3
• 作为产物：
  描述：

  4-甲基-呋喃-2,3-二羧酸 生成 4-甲基-3-呋喃甲酸
  参考文献：
  名称：

  合成β-甲基呋喃

  摘要：

  DOI：

  10.1002/hlca.19310140609

文献信息

• [EN] CYCLOOXYGENASE-2 INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE CYCLO-OXYGÉNASE 2 ET LEURS UTILISATIONS
  申请人：BROAD INST INC

  公开号：WO2021050700A1

  公开（公告）日：2021-03-18

  The present disclosure describes compounds of the formula: (I), (II), (III), (IV), (V). The compounds described herein may be cyclooxygenase (COX) (e.g., cyclooxygenase 2 (COX2)) inhibitors. The compounds may be radiolabeled. The compounds (e.g., radiolabeled compounds) may be useful (e.g., as positron emission tomography (PET) imaging agents) for diagnosing a disease. The compounds may also be useful for treating or preventing a disease. The present disclosure also describes pharmaceutical compositions and kits including the compounds; and methods of using the compounds.

  本公开描述了以下式的化合物：(I)，(II)，(III)，(IV)，(V)。本文描述的化合物可能是环氧合酶（COX）（例如，环氧合酶2（COX2））抑制剂。这些化合物可能被放射标记。这些化合物（例如，放射标记化合物）可能用于诊断疾病（例如，作为正电子发射断层扫描（PET）成像剂）。这些化合物也可能用于治疗或预防疾病。本公开还描述了包括这些化合物的药物组合物和试剂盒；以及使用这些化合物的方法。
• A brief, stereoselective total synthesis of the guaiane sesquiterpene (±)-gnididione
  作者：Colin P. Dell、David W. Knight

  DOI：10.1039/c39870000349

  日期：——

  A total synthesis of the guaiane sesquiterpene (±)-gnididione (1) has been achieved using carbanion chemistry at each key stage.

  在每个关键阶段都使用碳负离子化学技术完成了愈创树倍半萜烯（±）-gnididione（1）的全合成。
• Regioselective Preparation of 2,4-, 3,4-, and 2,3,4-Substituted Furan Rings. 2.¹ Regioselective Lithiation of 2-Silylated-3-substituted Furan Rings
  作者：Edward Bures、James A. Nieman、Shuyuan Yu、Patrick G. Spinazzé、Jean-Louis J. Bontront、Ian R. Hunt、Arvi Rauk、Brian A. Keay

  DOI：10.1021/jo971098b

  日期：1997.12.1

  A new method for the preparation of 3,4- and 2,5-disubstituted furan rings is described. A variety of 2-silylated-3-(hydroxymethyl)furans and 2-silylated-3-furoic acids lithiate exclusively at C-4 when treated with 2.2 equivs of BuLi. The resulting dianions were quenched with a variety of electrophiles to provide 2-silylated-3-(hydroxymethyl)-substituted furans and 2-silylated-4-substituted 3-furoic acids in good to excellent yields. Removal of the silyl group (n-Bu4NF) provided a variety of 4-substituted-3-(hydroxymethyl)furans and methyl 4-substituted-3-furoates, respectively. The latter esters were prepared due to difficulties encountered in isolating 4-substituted-3-furoic acids. The site of lithiation was altered by protecting the 3-hydroxyl group with a triethylsilane. Lithiation of 2-silylated-3-(((triethylsilyl)oxy)methyl)furan with 1.2 equivs of BuLi followed by the addition of electrophiles provided 2-silylated-3-(((triethylsilyl)oxy)methyl)-5-substituted furan rings. Subsequent removal of both silyl groups provided 2,4-disubstituted furan rings in moderate to good yields. A rationale is provided to explain why protection of the hydroxyl group at C-3 leads to a change in lithiation from the C-4 to the C-5 position of the furan ring. In addition, an explanation for the observed effect of adding HMPA or LiCl to the solution during the lithiation of 2-(tert-butyldimethylsilyl)-3-(hydroxymethyl)furan is provided.
• Synthesis and biological properties of novel glucocorticoid androstene C-17 furoate esters
  作者：David A. Sandham、Lucy Barker、David Beattie、David Beer、Louise Bidlake、David Bentley、Keith D. Butler、Sarah Craig、David Farr、Claire Ffoulkes-Jones、John R. Fozard、Sandra Haberthuer、Colin Howes、Deborah Hynx、Sarah Jeffers、Thomas H. Keller、Paul A. Kirkham、Janet C. Maas、Lazzaro Mazzoni、Andrew Nicholls、Gaynor E. Pilgrim、Elisabeth Schaebulin、Gillian M. Spooner、Rowan Stringer、Pamela Tranter、Katharine L. Turner、Morris F. Tweed、Christoph Walker、Simon J. Watson、Bernard M. Cuenoud

  DOI：10.1016/j.bmc.2004.06.027

  日期：2004.10

  A series of novel corticosteroid derivatives featuring C-17 furoate ester functionality have been synthesised. Profiling in vitro and in vivo has resulted in the identification of a compound with a longer duration of action and a lower oral side effect profile in rodents compared to budesonide. (C) 2004 Elsevier Ltd. All rights reserved.
• SYNTHESIS OF NEO-tANSHINLACTONE VIA THE PALLADIUM-MEDIATED INTRAMOLECULAR BIARYL COUPLING REACTION
  作者：Hitoshi Abe、Toshitaka Kawai、Yoshinori Komatsu、Yasuo Takeuchi、Yoshikazu Horino

  DOI：10.3987/com-12-s(n)87

  日期：——

  Neo-tanshinlactone (1) was synthesized by the intramolecular aryl-aryl coupling reaction of the precursor ester, which was prepared from the corresponding furan carboxylic acid (13) and naphthol (3), using a palladium reagent.