methyl 1-methoxymethyl-1H-indole-3-carboxylate | 446866-05-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl 1-methoxymethyl-1H-indole-3-carboxylate
• 英文别名: methyl 1-methoxymethylindole-3-carboxylate；Methyl 1-(methoxymethyl)indole-3-carboxylate
• CAS: 446866-05-3
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: ALALKVCEVIMQIG-UHFFFAOYSA-N

物化性质

• 熔点：
  64.9-65.7 °C
• 沸点：
  342.9±22.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 1-methoxymethyl-1H-indole-3-carboxylate 在 sodium hydroxide 、 水 、 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 生成 1-(甲氧基甲基)吲哚-3-羧酸
  参考文献：
  名称：

  Cyanopyrrolidines useful for the treatment of inter alia metabolic syndrome

  摘要：

  公开号：

  EP1595866B1
• 作为产物：
  描述：

  吲哚-3-甲酸甲酯 、 氯甲基甲基醚 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.25h， 以100%的产率得到methyl 1-methoxymethyl-1H-indole-3-carboxylate
  参考文献：
  名称：

  Hydroheteroarylation of Alkynes under Mild Nickel Catalysis

  摘要：

  Nickel complexes having a bulky tri(sec-alkyl)phosphine ligand catalyze hydroheteroarylation of alkynes at 35 degrees C. Selective activation of an Ar-H bond over an Ar-CN bond of N-protected 3-cyanoindoles is achieved by a proper choice of ligand and/or an N-protecting group. The catalysis is applicable to a diverse range of heteroarenes to afford cis-hydroheteroarylation products in highly chemo- and stereoselective manners. Excellent regioselectivity is observed with unsymmetrical alkynes to give the corresponding heteroaryl-substituted ethenes having a larger substituent trans to an aryl group.

  DOI：

  10.1021/ja0623459

文献信息

• Fluorescent Diarylindoles by Palladium-Catalyzed Direct and Decarboxylative Arylations of Carboxyindoles
  作者：Mitsuru Miyasaka、Azusa Fukushima、Tetsuya Satoh、Koji Hirano、Masahiro Miura

  DOI：10.1002/chem.200900098

  日期：2009.4.6

  efficiently undergo successive diarylation accompanied by CH bond cleavage and decarboxylation upon treatment with aryl bromides in the presence of a palladium catalyst system to afford fluorescent 2,3‐diarylindoles. This facile synthetic method provides a highly efficient blue emitter with a quantum yield of 0.97 in the solid state (see scheme).

  简单和灿烂：1-取代的1 ħ -吲哚-2-羧酸的有效经历连续diarylation伴随被C 在钯催化剂体系的存在下，得到荧光2,3- diarylindoles与芳基溴化物处理时H键裂解和脱羧。这种简便的合成方法提供了一种高效的蓝色发射器，固态时的量子产率为0.97（请参见方案）。
• Photochemistry of 2-Indolyl Aryl Ethers: An Unexpected Rearrangement Leading to C-C Bond Formation
  作者：Ken S. Feldman、Daniela Boneva Vidulova

  DOI：10.3987/com-03-9762

  日期：——

  Two types of 2-(p-tolyloxy)indole were prepared and their reactivity was studied under photochemical conditions. The expected electrocyclization was not observed. Instead, unprecedented rearrangement products were obtained. The reaction outcome was found to depend on the viscosity of the media.

  制备了两种类型的2-(对甲苯氧基)吲哚，并在光化学条件下研究了它们的反应性。没有观察到预期的电环化。相反，获得了前所未有的重排产物。发现反应结果取决于介质的粘度。
• Dihydropyrazolopyridine compounds and pharmaceutical use thereof
  申请人：——

  公开号：US20040052822A1

  公开（公告）日：2004-03-18

  The present invention provides dihydropyrazolopyridine compounds represented by the formula (I): 1 wherein each symbol is as defined in the specification, optically active forms thereof, and pharmaceutically acceptable salts thereof and hydrates thereof. The compounds of the present invention show a selective and strong inhibitory activity on glycogen synthase kinase-3 beta (GSK-3&bgr;), and are useful as medicaments for prevention and/or treatment of diabetes, diabetic complications and neurodegenerative diseases or as immunopotentiators.

  本发明提供了由式(I)所表示的二氢吡唑吡啶化合物：其中每个符号如规范中所定义，其光学活性形式和药学上可接受的盐及其水合物。本发明的化合物在糖原合酶激酶-3 beta（GSK-3β）上表现出选择性和强烈的抑制活性，并可用作预防和/或治疗糖尿病、糖尿病并发症和神经退行性疾病或作为免疫增强剂的药物。
• DIHYDROPYRAZOLOPYRIDINE COMPOUNDS AND PHARMACEUTICAL USE THEREOF
  申请人：Mitsubishi Pharma Corporation

  公开号：EP1355909A2

  公开（公告）日：2003-10-29
• US6977262B2
  申请人：——

  公开号：US6977262B2

  公开（公告）日：2005-12-20