4-chloro-2-(2'-furylmethylamino)phenol | 890657-57-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-chloro-2-(2'-furylmethylamino)phenol
• 英文别名: 4-Chloro-2-(furan-2-ylmethylamino)phenol
• CAS: 890657-57-5
• 化学式: C₁₁H₁₀ClNO₂
• 分子量: 223.659
• InChiKey: SBLIOYLCPQGMGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  45.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-chloro-2-(2'-furylmethylamino)phenol 在 potassium phosphate monohydrate 、 N,N-diisopropyl-2-(dicyclohexylphosphanyl)benzamide 、 水 、 palladium diacetate 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 3,4-dihydro-4-[(2-furyl)methyl]-3-oxo-6-(2-tolyl)-2H-1,4-benzoxazine
  参考文献：
  名称：

  Increasing appendage diversity on 3,4-dihydro-3-oxo-2H-1,4-benzoxazines via Aphos–Pd(OAc)2-catalyzed Suzuki–Miyaura cross-coupling of aryl chlorides

  摘要：

  A library of 32 members of 3,4-dihydro-3-oxo-2H-1,4-benzoxazines has been synthesized from two substituted 2-aminophenols via microwave-assisted one-pot regioselective annulation of 2-bromoalkanoates and subsequent Suzuki-Miyaura cross-coupling of the chloro-substituted scaffolds. The latter transformation was carried out using our Aphos-Pd(OAc)(2) catalyst and the coupling of the aryl chlorides with arylboronic acids proceeded under mild reaction conditions at 60-80 degrees C in THF-H2O (10:1) in the presence of K3PO4 center dot 3H(2)O as the base to furnish the corresponding biaryl products in 80-98% yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.057
• 作为产物：
  描述：

  糠醛 、 4-氯-2-氨基苯酚 在 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到4-chloro-2-(2'-furylmethylamino)phenol
  参考文献：
  名称：

  One-pot regioselective annulation toward 3,4-dihydro-3-oxo-2H-1,4-benzoxazine scaffolds under controlled microwave heating

  摘要：

  An efficient and general synthesis of 2-alkyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazines under controlled microwave heating has been established. It consists of a microwave-assisted reductive N-arylmethylation of substituted 2-aminophenols with aromatic aldehydes followed by a one-pot base-mediated regioselective O-alkylation of the N-arylmethyl-2-aminophenois with 2-bromoalkanoates to give the acyclic intermediates, which cyclize spontaneously to furnish the benzoxazine scaffolds in good to excellent yields. It was found that microwave heating over 180 degrees C was necessary for ring closure of the acyclic intermediates possessing an electron-withdrawing group. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.12.059

文献信息

• K₂CO₃/H₂O in [omim][BF₄] Ionic Liquid: A Green Medium for Efficient Room-Temperature Synthesis of<i>N</i>-Substituted 1,4-Benzoxazin-3-ones
  作者：Ali Sharifi、Mehdi Barazandeh、M. Saeed Abaee、Mojtaba Mirzaei

  DOI：10.1002/jhet.866

  日期：2012.7

  A medium consisting of K2CO3 and H2O in [omim][BF4] ionic liquid (IL) was used to synthesize N‐substituted 2H‐benzo[b][1,4]oxazin‐3(4H)‐one derivatives from their corresponding o‐aminophenols and 2‐bromoalkanoates. As a result, chemoselective formation of benzoxazinones in high yields has been observed at room temperature. After the reactions and separation of the products, the IL was recovered and

  使用在[omim] [BF 4 ]离子液体（IL）中由K 2 CO 3和H 2 O组成的介质合成N-取代的2 H-苯并[ b ] [1,4]恶嗪-3（4 H）-一种来自其相应的邻-氨基苯酚和2-溴代链烷酸酯的衍生物。结果，在室温下已观察到高产率的苯并恶嗪酮的化学选择性形成。在反应和产物分离之后，回收了IL，并成功地将其重新用于随后的反应中，而没有明显的活性损失。
• One-pot regioselective annulation toward 3,4-dihydro-3-oxo-2H-1,4-benzoxazine scaffolds under controlled microwave heating
  作者：Gaofeng Feng、Jinlong Wu、Wei-Min Dai

  DOI：10.1016/j.tet.2005.12.059

  日期：2006.5

  An efficient and general synthesis of 2-alkyl-3,4-dihydro-3-oxo-2H-1,4-benzoxazines under controlled microwave heating has been established. It consists of a microwave-assisted reductive N-arylmethylation of substituted 2-aminophenols with aromatic aldehydes followed by a one-pot base-mediated regioselective O-alkylation of the N-arylmethyl-2-aminophenois with 2-bromoalkanoates to give the acyclic intermediates, which cyclize spontaneously to furnish the benzoxazine scaffolds in good to excellent yields. It was found that microwave heating over 180 degrees C was necessary for ring closure of the acyclic intermediates possessing an electron-withdrawing group. (c) 2006 Elsevier Ltd. All rights reserved.
• Increasing appendage diversity on 3,4-dihydro-3-oxo-2H-1,4-benzoxazines via Aphos–Pd(OAc)2-catalyzed Suzuki–Miyaura cross-coupling of aryl chlorides
  作者：Gongli Yu、Yu Zheng、Jinlong Wu、Wei-Min Dai

  DOI：10.1016/j.tet.2013.09.057

  日期：2013.12

  A library of 32 members of 3,4-dihydro-3-oxo-2H-1,4-benzoxazines has been synthesized from two substituted 2-aminophenols via microwave-assisted one-pot regioselective annulation of 2-bromoalkanoates and subsequent Suzuki-Miyaura cross-coupling of the chloro-substituted scaffolds. The latter transformation was carried out using our Aphos-Pd(OAc)(2) catalyst and the coupling of the aryl chlorides with arylboronic acids proceeded under mild reaction conditions at 60-80 degrees C in THF-H2O (10:1) in the presence of K3PO4 center dot 3H(2)O as the base to furnish the corresponding biaryl products in 80-98% yields. (C) 2013 Elsevier Ltd. All rights reserved.