2-Bromo-5-[tert-butyl(dimethyl)silyl]oxyphenol | 1187189-23-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Bromo-5-[tert-butyl(dimethyl)silyl]oxyphenol
• CAS: 1187189-23-6
• 化学式: C₁₂H₁₉BrO₂Si
• 分子量: 303.271
• InChiKey: QNGMUIODUWKQFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Bromo-5-[tert-butyl(dimethyl)silyl]oxyphenol 在 ruthenium trichloride 、 sodium periodate 、 copper(l) iodide 、 Pd(PPh₃)₂Cl₂ 、 对甲苯磺酸 、 三乙基苯基氯化铵 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 26.0h， 生成
  参考文献：
  名称：

  Total synthesis of the 2-arylbenzo[b]furan-containing natural products from Artocarpus

  摘要：

  In this study, 2-arylbenzo[b]furan-containing derivatives moracin C (1) and moracin M (4), the natural products from Artocarpus, have been synthesized in highest overall yield to date (1, 7 steps with an overall yield of 41.9%; 4, 6 steps with an overall yield of 56.3%), and we also report the first total synthesis of artoindonesianin B-1 (2), another member of this family, in the same route (8 steps with an overall yield of 11.3%). This discovery provides a concise route for preparing enough amounts of 1, 2, and 4 as well as 2-arylbenzo[b]furan-containing natural product-like analogs (71-74) to explore the biological potential. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.05.093
• 作为产物：
  描述：

  3-((tert-butyldimethylsilyl)oxy)phenol 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以82%的产率得到2-Bromo-5-[tert-butyl(dimethyl)silyl]oxyphenol
  参考文献：
  名称：

  Total synthesis of the 2-arylbenzo[b]furan-containing natural products from Artocarpus

  摘要：

  In this study, 2-arylbenzo[b]furan-containing derivatives moracin C (1) and moracin M (4), the natural products from Artocarpus, have been synthesized in highest overall yield to date (1, 7 steps with an overall yield of 41.9%; 4, 6 steps with an overall yield of 56.3%), and we also report the first total synthesis of artoindonesianin B-1 (2), another member of this family, in the same route (8 steps with an overall yield of 11.3%). This discovery provides a concise route for preparing enough amounts of 1, 2, and 4 as well as 2-arylbenzo[b]furan-containing natural product-like analogs (71-74) to explore the biological potential. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.05.093

文献信息

• ortho-Formylation of oxygenated phenols
  作者：Øyvind W. Akselsen、Lars Skattebøl、Trond Vidar Hansen

  DOI：10.1016/j.tetlet.2009.08.101

  日期：2009.11

  Oxygenated phenols are mono-formylated using a mixture of paraformaldehyde, MgCl2, and Et3N in THF. In all cases but one, only one regioisomer of the salicylaldehyde is obtained in good to high yield. (C) 2009 Elsevier Ltd. All rights reserved.