Methyl-3-methylbenzo[c]isoxazole-6-carboxylate | 1395101-67-3

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: Methyl-3-methylbenzo[c]isoxazole-6-carboxylate
• 英文别名: Methyl 3-methyl-2,1-benzoxazole-6-carboxylate
• CAS: 1395101-67-3
• 化学式: C₁₀H₉NO₃
• 分子量: 191.186
• InChiKey: YDHADMMKIBOWMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-乙酰基-3-硝基苯甲酸甲酯 在 tin(II) chloride dihdyrate 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 20.0h， 以89%的产率得到Methyl-3-methylbenzo[c]isoxazole-6-carboxylate
  参考文献：
  名称：

  One-pot synthesis of 2,1-benzisoxazoles (anthranils) by a stannous chloride-mediated tandem reduction–heterocyclization of 2-nitroacylbenzenes under neutral conditions

  摘要：

  Classically, 2,1-benzisoxazoles (anthranils) are prepared from 2-nitroacylbenzenes by a reductive heterocyclization reaction with Sn or SnCl2 concentrated HCl. Acid sensitive functionalities are expected to be incompatible with these conditions; milder approaches to the synthesis of 2,1-benzisoxazoles would be welcomed. We demonstrate that SnCl2 center dot 2H(2)O in a 1:1 mixture of EtOAc/MeOH is capable of mediating the tandem reduction-heterocyclization of a variety of 2-nitroacylbenzenes to their corresponding 2,1-benzisoxazoles in good to excellent yields under essentially neutral conditions. Importantly, several commonly used acid-labile protecting groups, including Boc carbamate, tert-butyl ether, and tert-butyl ester, proved orthogonal to these reaction conditions. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.006

文献信息

• TREATMENT OF DISEASES WITH COMBINATIONS OF ALPHA 7 NICOTINIC ACETYLCHOLINE RECEPTOR AGONISTS AND OTHER COMPOUNDS
  申请人：Pharmacia & Upjohn Company LLC

  公开号：EP1572205A2

  公开（公告）日：2005-09-14
• COMBINATION FOR THE TREATMENT OF ADHD
  申请人：Pharmacia & Upjohn Company LLC

  公开号：EP1572300A1

  公开（公告）日：2005-09-14
• TREATMENT OF DISEASES WITH ALPHA-7 NACH RECEPTOR FULL AGONISTS
  申请人：Pharmacia & Upjohn Company LLC

  公开号：EP1587511A2

  公开（公告）日：2005-10-26
• [EN] NICOTINIC ACETYLCHOLINE AGONISTS IN THE TREATMENT OF GLAUCOMA AND RETINAL NEUROPATHY<br/>[FR] AGONISTES NICOTINIQUES DE L'ACETYLCHOLINE DANS LE TRAITEMENT DU GLAUCOME ET D'UNE NEUROPATHIE DE LA RETINE
  申请人：UPJOHN CO

  公开号：WO2004039366A1

  公开（公告）日：2004-05-13

  The invention provides a use or method of treating glaucoma, diabetic retinopathy, or age-related macular degeneration by the administration of α7 nAChR agonists to a mammal in need thereof.
• [EN] TREATMENT OF DISEASES WITH COMBINATIONS OF ALPHA 7 NICOTINIC ACETYLCHOLINE RECEPTOR AGONISTS AND OTHER COMPOUNDS<br/>[FR] TRAITEMENT DE MALADIES A L'AIDE DE COMBINAISONS D'AGONISTES DU RECEPTEUR NICOTINIQUE DE L'ACETYLCHOLINE ALPHA 7 ET D'AUTRES COMPOSES
  申请人：UPJOHN CO

  公开号：WO2004052348A2

  公开（公告）日：2004-06-24

  The present invention relates to compositions and methods to treat diseases or condition with an α nAChR full agonist and an inhibitor of cholinesterase, and or beta secretase and or gamma secretase.