tert-butyl benzo[c]isoxazole-6-carboxylate | 1395101-72-0

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: tert-butyl benzo[c]isoxazole-6-carboxylate
• 英文别名: Tert-butyl 2,1-benzoxazole-6-carboxylate；tert-butyl 2,1-benzoxazole-6-carboxylate
• CAS: 1395101-72-0
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: XCQZESPRAHLXCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  tert-butyl 4-formyl-3-nitrobenzoate 在 tin(II) chloride dihdyrate 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 20.0h， 以78%的产率得到tert-butyl benzo[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

• One-pot synthesis of 2,1-benzisoxazoles (anthranils) by a stannous chloride-mediated tandem reduction–heterocyclization of 2-nitroacylbenzenes under neutral conditions
  作者：Jay Chauhan、Steven Fletcher

  DOI：10.1016/j.tetlet.2012.07.006

  日期：2012.9

  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.