2-(2-bromo-5-isopropoxy-4-methoxyphenyl)ethyl p-toluenesulfonate | 850346-69-9

• 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-(2-bromo-5-isopropoxy-4-methoxyphenyl)ethyl p-toluenesulfonate
• 英文别名: 2-(2-Bromo-4-methoxy-5-propan-2-yloxyphenyl)ethyl 4-methylbenzenesulfonate
• CAS: 850346-69-9
• 化学式: C₁₉H₂₃BrO₅S
• 分子量: 443.359
• InChiKey: WOCVRKLBKCKESK-UHFFFAOYSA-N

物化性质

• 沸点：
  534.2±50.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-bromo-5-isopropoxy-4-methoxyphenyl)ethyl p-toluenesulfonate 在 bis-triphenylphosphine-palladium(II) chloride 、 四(三苯基膦)钯 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 、 sodium carbonate 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 62.5h， 生成 methyl 2-bromo-8-isopropoxy-1-(4-isopropoxy-3-methoxyphenyl)-9-methoxy-5,6-dihydropyrrolo[2,1-a]isoquinoline-3-carboxylate
  参考文献：
  名称：

  Modular Total Synthesis of Lamellarin D

  摘要：

  A modular total synthesis of lamellarin D, a marine alkaloid with potent cytotoxic as well as topoisomerase I inhibition properties, has been accomplished. A sequential and regioselective bromination/Suzuki cross-coupling procedure was applied for the introduction of aryl groups at positions 1 and 2 of scaffold 1. Microwave-assisted 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) oxidation to yield pyrroloisoquinoline 15, followed by phenol group deprotection and subsequent lactonization, gave lamellarin D (18% in eight steps from 1).

  DOI：

  10.1021/jo051083a
• 作为产物：
  描述：

  2-bromo-4-methoxy-5-(1-methylethoxy)benzaldehyde 在 4-二甲氨基吡啶 、 dimethyl sulfide borane 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 2-(2-bromo-5-isopropoxy-4-methoxyphenyl)ethyl p-toluenesulfonate
  参考文献：
  名称：

  Modular Total Synthesis of Lamellarin D

  摘要：

  A modular total synthesis of lamellarin D, a marine alkaloid with potent cytotoxic as well as topoisomerase I inhibition properties, has been accomplished. A sequential and regioselective bromination/Suzuki cross-coupling procedure was applied for the introduction of aryl groups at positions 1 and 2 of scaffold 1. Microwave-assisted 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) oxidation to yield pyrroloisoquinoline 15, followed by phenol group deprotection and subsequent lactonization, gave lamellarin D (18% in eight steps from 1).

  DOI：

  10.1021/jo051083a

文献信息

• 5,6-Dihydropyrrolo[2,1-b]isoquinolines as scaffolds for synthesis of lamellarin analogues
  作者：Christian A. Olsen、Núria Parera、Fernando Albericio、Mercedes Álvarez

  DOI：10.1016/j.tetlet.2005.01.145

  日期：2005.3

  Efficient modular synthetic routes to open chain marine alkaloids such as lamellarins have been developed. 5,6-Dihydropyrrolo[2, 1-b]isoquinoline scaffolds were prepared, and protocols enabling regioselective bromination followed by Suzuki cross-coupling were established for the introduction of aryl groups onto the 2- and 3-positions. (C) 2005 Elsevier Ltd. All rights reserved.