4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylic acid methyl ester | 1227664-13-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylic acid methyl ester
• 英文别名: methyl 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate
• CAS: 1227664-13-2
• 化学式: C₁₃H₁₉BO₄S
• 分子量: 282.168
• InChiKey: GFIHVXCYZMZVNQ-UHFFFAOYSA-N

物化性质

• 沸点：
  393.9±42.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  73
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylic acid methyl ester 在 potassium phosphate 、 四(三苯基膦)钯 、 溴 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 26.25h， 生成 ethyl 5-(4-chlorophenyl)-4-methyl-3-(3-methyl-4-sulfamoylphenyl)thiophene-2-carboxylate
  参考文献：
  名称：

  HETEROARYL DERIVATIVES AS ALPHA7 NACHR MODULATORS

  摘要：

  公开的是一种具有式（I）的化合物，其中Z、m和R1-R6如本文所述，作为尤其是α7亚型的尼古丁乙酰胆碱受体的调节剂，在需要的受试者中使用，以及类似物、前药、同位素替代物、代谢物、药学上可接受的盐、多型体、溶剂合物、异构体、包合物和其共晶，可单独使用或与适当的其他药物组合使用，以及含有这种化合物和类似物的药物组合物。还公开了一种制备这些化合物的方法及其在治疗中的预期用途，特别是在预防和治疗阿尔茨海默病、轻度认知障碍、老年性痴呆等疾病中的用途。

  公开号：

  US20130331387A1
• 作为产物：
  描述：

  4-甲基噻吩-2-甲基羧酸盐 、 联硼酸频那醇酯 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 作用下， 以 正己烷 为溶剂， 反应 5.0h， 以92%的产率得到4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Ester-Directed Regioselective Borylation of Heteroarenes Catalyzed by a Silica-Supported Iridium Complex

  摘要：

  The ester-directed regioselective borylation of arenes catalyzed by a silica-supported monophosphine-Ir complex displayed a significantly broad substrate scope toward heteroaromatic compounds, including thiophene. pyrrole, furan, benzothiophene, benzofuran, indole, and carbazole derivatives. The regioselectivity is complementary to the selectivities observed in the heteroarene C-H borylation with the dtbpy-Ir catalyst system.

  DOI：

  10.1021/jo100352b

文献信息

• Heteroaryl derivatives as alpha7 nAChR modulators
  申请人：Sinha Neelima

  公开号：US09072731B2

  公开（公告）日：2015-07-07

  Disclosed is a compound of formula (I), wherein Z, m and R1-R6 are as described herein, as a modulator of nicotinic acetylcholine receptors particularly the α7 subtype, in a subject in need thereof, as well as analogs, prodrugs, isotopically substituted analogs, metabolites, pharmaceutically acceptable salts, polymorphs, solvates, isomers, clathrates, and co-crystal thereof, for use either alone or in combinations with suitable other medicaments, and pharmaceutical compositions containing such compounds and analogs. Also disclosed are a process of preparation of the compounds and the intended uses thereof in therapy, particularly in the prophylaxis and therapy of disorders such as Alzheimer's disease, mild cognitive impairment, senile dementia, and the like.

  本发明揭示了一种式为（I）的化合物，其中Z，m和R1-R6如本文所述，作为尼古丁酸乙酰胆碱受体特别是α7亚型的调节剂，用于需要此类治疗的患者，以及其类似物、前药、同位素替代类似物、代谢物、药学上可接受的盐、多晶型、溶剂化物、异构体、笼合物和共晶体，可单独使用或与适当的其他药物组合使用，以及包含此类化合物和类似物的制药组合物。本发明还揭示了制备该化合物的方法及其在治疗中的预防和治疗，特别是在阿尔茨海默病、轻度认知障碍、老年痴呆症等疾病的预防和治疗中的预期用途。
• Heteroaryl Derivatives as Alpha7 NACHR Modulators
  申请人：Lupin Limited

  公开号：US20150231143A1

  公开（公告）日：2015-08-20

  Disclosed is a compound of formula I: wherein Z, m and R 1 -R 6 are as described herein, as a modulator of nicotinic acetylcholine receptors particularly the α7 subtype, in a subject in need thereof, as well as analogues, prodrugs, isotopically substituted analogs, metabolites, pharmaceutically acceptable salts, polymorphs, solvates, isomers, clathrates, and co-crystal thereofs, for use either alone or in combinations with suitable other medicaments, and pharmaceutical compositions containing such compounds and analogues. Also disclosed are a process of preparation of the compounds and the intended uses thereof in therapy, particularly in the prophylaxis and therapy of disorders such as Alzheimer's disease, mild cognitive impairment, senile dementia, and the like.

  本发明涉及一种化合物，其化学式为I：其中Z、m和R1-R6如本文所述，作为尼古丁乙酰胆碱受体的调节剂，特别是α7亚型，在需要的受体中使用，以及类似物、前药、同位素替代物、代谢物、药学上可接受的盐、多晶型、溶剂合物、异构体、包合物和共晶体，可单独使用或与适当的其他药物组合使用，以及包含这种化合物和类似物的制药组合物。还公开了制备这些化合物的过程以及它们在治疗中的预防和治疗中的预期用途，特别是在阿尔茨海默病、轻度认知障碍、老年性痴呆等疾病的预防和治疗中使用。
• [EN] HETEROARYL DERIVATIVES AS ALPHA7 NACHR MODULATORS<br/>[FR] DÉRIVÉS HÉTÉROARYLE À TITRE DE MODULATEURS DES NACHR ALPHA 7
  申请人：LUPIN LTD

  公开号：WO2012114285A9

  公开（公告）日：2012-10-18
• HETEROARYL DERIVATIVES AS ALPHA7 NACHR MODULATORS
  申请人：Sinha Neelima

  公开号：US20130331387A1

  公开（公告）日：2013-12-12

  Disclosed is a compound of formula (I), wherein Z, m and R 1 -R 6 are as described herein, as a modulator of nicotinic acetylcholine receptors particularly the α7 subtype, in a subject in need thereof, as well as analogues, prodrugs, isotopically substituted analogs, metabolites, pharmaceutically acceptable salts, polymorphs, solvates, isomers, clathrates, and co-crystal thereof, for use either alone or in combinations with suitable other medicaments, and pharmaceutical compositions containing such compounds and analogues. Also disclosed are a process of preparation of the compounds and the intended uses thereof in therapy, particularly in the prophylaxis and therapy of disorders such as Alzheimer's disease, mild cognitive impairment, senile dementia, and the like.

  公开的是一种具有式（I）的化合物，其中Z、m和R1-R6如本文所述，作为尤其是α7亚型的尼古丁乙酰胆碱受体的调节剂，在需要的受试者中使用，以及类似物、前药、同位素替代物、代谢物、药学上可接受的盐、多型体、溶剂合物、异构体、包合物和其共晶，可单独使用或与适当的其他药物组合使用，以及含有这种化合物和类似物的药物组合物。还公开了一种制备这些化合物的方法及其在治疗中的预期用途，特别是在预防和治疗阿尔茨海默病、轻度认知障碍、老年性痴呆等疾病中的用途。
• Ester-Directed Regioselective Borylation of Heteroarenes Catalyzed by a Silica-Supported Iridium Complex
  作者：Soichiro Kawamorita、Hirohisa Ohmiya、Masaya Sawamura

  DOI：10.1021/jo100352b

  日期：2010.6.4

  The ester-directed regioselective borylation of arenes catalyzed by a silica-supported monophosphine-Ir complex displayed a significantly broad substrate scope toward heteroaromatic compounds, including thiophene. pyrrole, furan, benzothiophene, benzofuran, indole, and carbazole derivatives. The regioselectivity is complementary to the selectivities observed in the heteroarene C-H borylation with the dtbpy-Ir catalyst system.