(5-bromo(2H-benzo[d]1,3-dioxolan-4-yl))methoxymethane | 669051-20-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (5-bromo(2H-benzo[d]1,3-dioxolan-4-yl))methoxymethane
• 英文别名: 5-Bromo-4-(methoxymethyl)benzo[d][1,3]dioxole；5-bromo-4-(methoxymethyl)-1,3-benzodioxole
• CAS: 669051-20-1
• 化学式: C₉H₉BrO₃
• 分子量: 245.073
• InChiKey: HHKYJPJLSXPQPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5-bromo(2H-benzo[d]1,3-dioxolan-4-yl))methoxymethane 在 palladium diacetate 、 正丁基锂 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.58h， 生成 2-methoxy-5-[4-(methoxymethyl)(2H-benzo[d]1,3-dioxolen-5-yl)]-cyclohepta-2,4,6-trien-1-one
  参考文献：
  名称：

  Practical synthesis of biaryl colchicinoids containing 3′,4′-catechol ether-based A-rings via Suzuki cross-coupling with ligandless palladium in water

  摘要：

  Eight new biaryl colchicinoids containing 3',4'-methylene or benzodioxy ether bridges were synthesized. The key synthetic step employed a ligandless, aqueous Suzuki cross-coupling reaction catalyzed by Pd(OAc)(2) with tetrabutylammonium bromide (TBAB) and potassium carbonate (K2CO3). The biaryl Suzuki products were typically formed in 5-30 min and always in less than 1 h. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.016
• 作为产物：
  描述：

  1,3-苯并二氧戊环-4-烷基甲醇 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 (5-bromo(2H-benzo[d]1,3-dioxolan-4-yl))methoxymethane
  参考文献：
  名称：

  Practical synthesis of biaryl colchicinoids containing 3′,4′-catechol ether-based A-rings via Suzuki cross-coupling with ligandless palladium in water

  摘要：

  Eight new biaryl colchicinoids containing 3',4'-methylene or benzodioxy ether bridges were synthesized. The key synthetic step employed a ligandless, aqueous Suzuki cross-coupling reaction catalyzed by Pd(OAc)(2) with tetrabutylammonium bromide (TBAB) and potassium carbonate (K2CO3). The biaryl Suzuki products were typically formed in 5-30 min and always in less than 1 h. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.016

文献信息

• BODIPY STRUCTURE FLUORESCENCE PROBES FOR DIVERSE BIOLOGICAL APPLICATIONS
  申请人：National University of Singapore

  公开号：EP2794620B1

  公开（公告）日：2017-11-15
• Practical synthesis of biaryl colchicinoids containing 3′,4′-catechol ether-based A-rings via Suzuki cross-coupling with ligandless palladium in water
  作者：Amy Morin Deveau、Timothy L. Macdonald

  DOI：10.1016/j.tetlet.2003.11.016

  日期：2004.1

  Eight new biaryl colchicinoids containing 3',4'-methylene or benzodioxy ether bridges were synthesized. The key synthetic step employed a ligandless, aqueous Suzuki cross-coupling reaction catalyzed by Pd(OAc)(2) with tetrabutylammonium bromide (TBAB) and potassium carbonate (K2CO3). The biaryl Suzuki products were typically formed in 5-30 min and always in less than 1 h. (C) 2003 Elsevier Ltd. All rights reserved.