3-methylbenzofuran-6-ol | 3652-66-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3-methylbenzofuran-6-ol
• 英文别名: 3-methyl-6-hydroxybenzofuran；6-hydroxy-3-methylbenzofuran；3-methyl-benzofuran-6-ol；3-Methyl-1-benzofuran-6-ol；6-Oxy-3-methyl-cumaron
• CAS: 3652-66-2
• 化学式: C₉H₈O₂
• 分子量: 148.161
• InChiKey: QHWIITORDRWUMO-UHFFFAOYSA-N

物化性质

• 熔点：
  103 °C
• 沸点：
  124.9±10.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  3-methylbenzofuran-6-ol 在 三氯化铝 、 sodium acetate 、 硝基苯 作用下， 生成 1-(6-hydroxy-3-methyl-benzofuran-2-yl)-ethanone
  参考文献：
  名称：

  Shah; Shah, Chemische Berichte, 1959, vol. 92, p. 2933,2936

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(2-bromoallyloxy)-phenol 在 trans-di(μ-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium(II) potassium carbonate 、 caesium carbonate 作用下， 以 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 生成 3-methylbenzofuran-6-ol
  参考文献：
  名称：

  阴离子加速钯介导的分子内环化：苯并呋喃，吲哚和苯并吡喃的合成

  摘要：

  使用卤代乙烯与酚的分子内交叉偶联获得取代的苯并稠合的杂环，例如吲哚，苯并呋喃和苯并吡喃。该转化代表了通往这些杂环的新途径，并且是在阴离子条件下使用钯环催化剂完成的。©1997爱思唯尔科学有限公司。

  DOI：

  10.1016/s0040-4039(97)01468-8

文献信息

• Regiodivergent Halogenation of Vinylogous Esters: One-Pot, Transition-Metal-Free Access to Differentiated Haloresorcinols
  作者：Xiaohong Chen、Jenny S. Martinez、Justin T. Mohr

  DOI：10.1021/ol503561x

  日期：2015.1.16

  vinylogous esters and sulfonyl halide halogen donors. Either the 4- or 6-haloresorcinol isomer is accessible from a common precursor. In contrast to conventional oxidants for arene halogenation, mild sulfonyl halides allow broad functional group compatibility. The strategy inherently differentiates the two resorcinol oxygen atoms and enhances the potential for complex molecule synthesis.

  我们报告了一种高效的方法，用于使用容易获得的乙烯基酯和磺酰卤卤素供体进行卤代间苯二酚衍生物的区域发散合成。4-或6-卤代间苯二酚异构体可从常见的前体获得。与用于芳烃卤化的常规氧化剂相比，温和的磺酰卤具有广泛的官能团相容性。该策略固有地区分了两个间苯二酚氧原子，并增强了复杂分子合成的潜力。
• 2-aminoethyl-benzofuran derivatives, preparation thereof and
  申请人：Synthelabo

  公开号：US06063810A1

  公开（公告）日：2000-05-16

  Compounds of formula (I), wherein A is a hydrogen atom or a hydroxyl group; B is a hydrogen atom or a C.sub.1-8 alkyl, C.sub.1-8 alkenyl, C.sub.1-8 fluoroalkyl or C.sub.1-8 perfluoroalkyl group; each of R.sub.1, R.sub.2 and R.sub.5, which are the same or different, is a hydrogen atom, a halogen such as chlorine, bromine or fluorine, a C.sub.1-8 alkyl, C.sub.1-8 alkenyl, C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkenyl, C.sub.6, C.sub.10 or C.sub.14 aryl, C.sub.1-6 alkoxycarbonyl, C.sub.1-6 hydroxyalkyl, C.sub.1-6 alkoxyalkyl, C.sub.1-6 alkoxy, C.sub.1-8 fluoroalkyl or C.sub.1-8 perfluoroalkyl group, or R.sub.1 and R.sub.2 taken together form a C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkenyl or C.sub.6, C.sub.10 or C.sub.14 aryl ring, except for compounds in which R.sub.1 and R.sub.2 are both hydrogen; each of R.sub.3 and R.sub.4, which are the same or different, is a hydrogen atom or a C.sub.1-8 alkyl, C.sub.1-8 alkenyl, C.sub.3-8 cycloalkyl or C.sub.3-8 cycloalkenyl group, or R.sub.3 and R.sub.4 taken together form a C.sub.2-6 cycloalkyl or C.sub.3-6 cycloalkenyl ring, e.g., piperidyl, azetidinyl or pyrrolidyl; in the form of enantiomers, diastereoisomers or mixtures thereof, including racemic mixtures;, as well as pharmaceutically acceptable acid addition salts thereof. The compounds may be used in therapy.

  式(I)的化合物，其中A是氢原子或羟基；B是氢原子或C.sub.1-8烷基，C.sub.1-8烯基，C.sub.1-8氟烷基或C.sub.1-8全氟烷基基团；R.sub.1，R.sub.2和R.sub.5中的每一个，它们相同或不同，是氢原子，卤素如氯，溴或氟，C.sub.1-8烷基，C.sub.1-8烯基，C.sub.3-8环烷基，C.sub.3-8环烯基，C.sub.6，C.sub.10或C.sub.14芳基，C.sub.1-6烷氧羰基，C.sub.1-6羟基烷基，C.sub.1-6烷氧基烷基，C.sub.1-6烷氧基，C.sub.1-8氟烷基或C.sub.1-8全氟烷基基团，或R.sub.1和R.sub.2一起形成C.sub.3-8环烷基，C.sub.3-8环烯基或C.sub.6，C.sub.10或C.sub.14芳基环，但不包括R.sub.1和R.sub.2均为氢的化合物；R.sub.3和R.sub.4中的每一个，它们相同或不同，是氢原子或C.sub.1-8烷基，C.sub.1-8烯基，C.sub.3-8环烷基或C.sub.3-8环烯基基团，或R.sub.3和R.sub.4一起形成C.sub.2-6环烷基或C.sub.3-6环烯基环，例如哌啶基，氮杂环丙基或吡咯基；以对映体，非对映异构体或它们的混合物的形式存在，包括外加药用酸盐。这些化合物可用于治疗。
• Antidiabetic bicyclic compounds
  申请人：Ge Min

  公开号：US20070265332A1

  公开（公告）日：2007-11-15

  Tricyclic compounds containing a cyclopropyl carboxylic acid or carboxylic acid derivative (e.g. amide) fused to a bicyclic ring, including pharmaceutically acceptable salts and prodrugs thereof, are agonists of G-protein coupled receptor 40 (GPR40) and are useful as therapeutic compounds, particularly in the treatment of Type 2 diabetes mellitus, and of conditions that are often associated with this disease, including obesity and lipid disorders, such as mixed or diabetic dyslipidemia, hyperlipidemia, hypercholesterolemia, and hypertriglyceridemia.

  含有环丙基羧酸或羧酸衍生物（如酰胺）的三环化合物与融合到双环环上的G蛋白偶联受体40（GPR40）是激动剂，并且可用作治疗化合物，特别是在治疗2型糖尿病方面，以及与该疾病常相关的病症，包括肥胖和脂质紊乱，如混合性或糖尿病性脂质代谢异常、高血脂、高胆固醇血症和高甘油三酯血症。
• Toluene dioxygenase-catalyzed cis-dihydroxylation of benzo[b]thiophenes and benzo[b]furans: synthesis of benzo[b]thiophene 2,3-oxide
  作者：Derek R. Boyd、Narain D. Sharma、Ian N. Brannigan、Timothy A. Evans、Simon A. Haughey、Brian T. McMurray、John F. Malone、Peter B. A. McIntyre、Paul J. Stevenson、Christopher C. R. Allen

  DOI：10.1039/c2ob26120k

  日期：——

  cis-dihydroxylation of benzo[b]thiophene, benzo[b]furan and several methyl substituted derivatives was found to occur in both the carbocyclic and heterocyclic rings. Relative and absolute configurations and enantiopurities of the resulting dihydrodiols were determined. Hydrogenation of the alkene bond in carbocyclic cis-dihydrodiols and ring-opening epimerization/reduction reactions of heterocyclic cis/trans-dihydrodiols

  发现苯并[ b ]噻吩，苯并[ b ]呋喃和几种甲基取代的衍生物的酶促顺式-二羟基化在碳环和杂环中均发生。确定了所得二氢二醇的相对和绝对构型以及对映体纯度。还研究了碳环顺式-二氢二醇中烯烃键的氢化和杂环式顺式/反式-二氢二醇的开环差向异构/还原反应。苯并[ b ]噻吩和苯并[ b ]呋喃的相对稳定的杂环二氢二醇显示出对反式的强烈偏好在水溶液中的构型。苯并[ b ]噻吩的2,3-二氢二醇代谢物在不稳定的氧化芳烃苯并[ b ]噻吩2,3-氧化物的化学酶法合成中用作前体。
• Topically active carbonic anhydrase inhibitors. 3. Benzofuran- and indole-2-sulfonamides
  作者：Samuel L. Graham、Jacob M. Hoffman、Pierre Gautheron、Stuart R. Michelson、Thomas H. Scholz、Harvey Schwam、Kenneth L. Shepard、Anthony M. Smith、Robert L. Smith

  DOI：10.1021/jm00164a045

  日期：1990.2

  Derivatives of benzofuran- and indole-2-sulfonamide were prepared for evaluation as topically active ocular hypotensive agents. These compounds were found to be excellent inhibitors of carbonic anhydrase and to lower intraocular pressure in a rabbit model of ocular hypertension. However, the development of these compounds for clinical use was precluded by the observation that they cause dermal sensitization

  制备苯并呋喃-和吲哚-2-磺酰胺的衍生物作为局部活性的眼用降压药进行评估。在兔子高眼压症模型中，发现这些化合物是出色的碳酸酐酶抑制剂，并能降低眼内压。然而，由于观察到它们引起豚鼠的皮肤致敏作用而阻止了这些化合物用于临床用途的开发。进一步证明了亲电性（通过与还原型谷胱甘肽的体外反应性评估）与皮肤致敏性之间的相关性。