methyl 3-phenylbenzo[b]thiophene-2-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: methyl 3-phenylbenzo[b]thiophene-2-carboxylate
• 英文别名: 3-Phenylbenzo[b]thiophene-2-carboxylic acid methyl ester；methyl 3-phenyl-1-benzothiophene-2-carboxylate
• 化学式: C₁₆H₁₂O₂S
• 分子量: 268.336
• InChiKey: IHAFEVZYEBKJDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 3-phenylbenzo[b]thiophene-2-carboxylate 在 水 、 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 以95%的产率得到3-phenylbenzo[b]thiophene-2-carboxylic acid
  参考文献：
  名称：

  Investigation of thiazolyl–benzothiophenamides as potential agents for African sleeping sickness

  摘要：

  非洲睡眠病是一种潜在致命的忽视疾病，影响撒哈拉以南的非洲。

  DOI：

  10.1039/d0md00277a
• 作为产物：
  描述：

  2-硝基苯甲腈 在 potassium phosphate 、 四(三苯基膦)钯 、 亚硝酸特丁酯 、 potassium hydroxide 、 copper(ll) bromide 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 7.0h， 生成 methyl 3-phenylbenzo[b]thiophene-2-carboxylate
  参考文献：
  名称：

  Design and synthesis of condensed thienocoumarins by Suzuki–Miyaura reaction/lactonization tandem protocol

  摘要：

  A concise and efficient approach to a series of chromen-4-ones with fused thiophene ring has been developed using the Suzuki-Miyaura reaction of bromothiophene-2- and 3-carboxylates with 2-methoxyboronic acids and subsequent cyclization of prepared alkyl (2-methoxy)aryl thiophene-2- and 3-carboxylates under the action of BBr3/KOtBu. Starting bromothiophenes are easily obtained from corresponding commercially available aminothiophenes by diazotization/bromination reaction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.096

文献信息

• Room-Temperature Suzuki-Miyaura Coupling of Heteroaryl Chlorides and Tosylates
  作者：Junfeng Yang、Sijia Liu、Jian-Feng Zheng、Jianrong Steve Zhou

  DOI：10.1002/ejoc.201200918

  日期：2012.11

  Suzuki–Miyaura coupling of heteroaryls is an important method for the preparation of compound libraries for medicinal chemistry and materials research. Although many catalysts have been developed, none of them have been generally applicable to the coupling reactions of heteroaryl chlorides and tosylates at room temperature. We discovered that a catalyst combination of Pd(OAc)2 and XPhos (2-dicyclohexylphosphanyl-2′

  杂芳基的 Suzuki-Miyaura 偶联是制备用于药物化学和材料研究的化合物库的重要方法。尽管已经开发了许多催化剂，但它们都没有普遍适用于杂芳基氯与甲苯磺酸酯在室温下的偶联反应。我们发现 Pd(OAc)2 和 XPhos（2-二环己基膦酰基-2',4',6'-三异丙基联苯）的催化剂组合可以有效地催化这些偶联。除了催化剂的选择，在含水醇溶剂中使用氢氧化物碱对于快速偶联也是必不可少的。这些条件促进了活性催化剂（XPhos）Pd0 的快速释放，并加速了催化循环中的金属转移。大多数杂芳基氯（31 个实例）和甲苯磺酸盐（17 个实例）的主要家族在室温下在几分钟到几小时内达到完全转化。该方法可以很容易地扩大规模以进行克级合成。此外，我们检查了整个反应中偶联伙伴的相对反应性。富电子杂芳基氯化物和甲苯磺酸盐的反应速度比缺电子杂芳基化合物慢，顺序为吲哚、吡咯呋喃、噻吩>吡啶。类似地，缺电子芳基硼酸的反应
• METHOD FOR PROMOTING PLANT GROWTH
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20150282482A1

  公开（公告）日：2015-10-08

  The present invention provides a method for promoting plant growth, which comprises treating a plant with a compound represented by the following Formula (1): provided that a method for promoting plant growth which comprises treating plants with a compound corresponding to any one of the following (1) to (8) is excluded: (1) Methyl 4-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, (2) Methyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, (3) Methyl 6-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, (4) Methyl 7-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, (5) Ethyl 4-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, (6) Ethyl 5-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, (7) Ethyl 6-(trifluoromethyl)benzo[b]thiophene-2-carboxylate, and (8) Ethyl 7-(trifluoromethyl)benzo[b]thiophene-2-carboxylate.

  本发明提供了一种促进植物生长的方法，包括用下式表示的化合物处理植物： 只要排除用与以下任一化合物相对应的化合物处理植物的促进植物生长方法：(1) 甲基4-(三氟甲基)苯并[b]噻吩-2-羧酸酯，(2) 甲基5-(三氟甲基)苯并[b]噻吩-2-羧酸酯，(3) 甲基6-(三氟甲基)苯并[b]噻吩-2-羧酸酯，(4) 甲基7-(三氟甲基)苯并[b]噻吩-2-羧酸酯，(5) 乙基4-(三氟甲基)苯并[b]噻吩-2-羧酸酯，(6) 乙基5-(三氟甲基)苯并[b]噻吩-2-羧酸酯，(7) 乙基6-(三氟甲基)苯并[b]噻吩-2-羧酸酯，以及(8) 乙基7-(三氟甲基)苯并[b]噻吩-2-羧酸酯。
• Facile Access to Benzothiophenes through Metal-Free Iodine-­Catalyzed Intermolecular Cyclization of Thiophenols and Alkynes
  作者：Daoshan Yang、Hua Wang、Kelu Yan、Mengqi Zhang、Wei Wei、Yao Liu、Laijin Tian

  DOI：10.1055/s-0034-1378841

  日期：——

  A novel iodine-catalyzed method for the synthesis of benzothiophene derivatives through cascade reactions of substituted thiophenols with alkynes has been demonstrated under metal- and solvent-free conditions. The present protocol uses inexpensive and environmentally friendly molecular iodine as the catalyst, and the corresponding products are obtained in moderate to excellent yields. Such an efficient

  在无金属和无溶剂条件下，证明了一种通过取代苯硫酚与炔烃的级联反应合成苯并噻吩衍生物的新型碘催化方法。本协议使用廉价且环保的分子碘作为催化剂, 并以中等至优良的收率获得相应的产品。这种高效、经济和绿色的转化应该为有机和药物化学中的各种苯并噻吩提供一种有吸引力的方法。
• [EN] INHIBITORS OF HISTONE DEACETYLASE<br/>[FR] INHIBITEURS DE L'HISTONE DÉACÉTYLASE
  申请人：METHYLGENE INC

  公开号：WO2009055917A1

  公开（公告）日：2009-05-07

  This invention relates to compounds and methods for the inhibition of HDAC enzymatic activity. More particularly, the invention provides for compounds of formula (I), (I) and N-oxides, hydrates, solvates, pharmaceutically acceptable salts, prodrugs and complexes thereof, and racemic and scalemic mixtures, diastereomers and enantiomers thereof, wherein L, M, n, R, W, X and Y are as defined in the specification.

  这项发明涉及化合物和用于抑制HDAC酶活性的方法。更具体地，该发明提供了符合式(I)、(I)和N-氧化物、水合物、溶剂合物、药用可接受盐、前药和其复合物、外消旋和手性混合物、非对映异构体和对映体的化合物，其中L、M、n、R、W、X和Y如规范中定义的。
• <i>ortho</i> ‐C−H Arylation of Benzoic Acids with Aryl Bromides and Chlorides Catalyzed by Ruthenium
  作者：Agostino Biafora、Thilo Krause、Dagmar Hackenberger、Florian Belitz、Lukas J. Gooßen

  DOI：10.1002/anie.201607270

  日期：2016.11.14

  of catalytic amounts of [(p‐cym)RuCl2]2/PEt3⋅HBF4, K2CO3 as the base, and NMP as the solvent efficiently mediates the ortho‐C−H arylation of benzoic acids with aryl bromides at 100 °C. Replacing the phosphine ligand with the amino acid dl‐pipecolinic acid enables the analogous transformation with aryl chlorides. The key advantage of this broadly applicable transformation is the use of an inexpensive

  包括催化量的一种系统，[（p -cym）的RuCl 2 ] 2 / PET 3 ⋅HBF 4，K 2 CO 3作为碱，和NMP作为溶剂有效地介导了邻位的苯甲酸与-C-H芳基化100°C时的芳基溴化物。用氨基酸dl-胡椒碱取代膦配体可实现与芳基氯化物的类似转化。这种广泛适用的转化方法的主要优点是使用廉价的钌催化剂，结合简单的羧酸盐作为导向基团，可以将其无痕除去或用作脱羧ipso的锚定点 换人。