2-bromo-5-isopropoxy-4-methoxystyrene | 867313-46-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-bromo-5-isopropoxy-4-methoxystyrene
• 英文别名: 1-Bromo-2-ethenyl-5-methoxy-4-propan-2-yloxybenzene
• CAS: 867313-46-0
• 化学式: C₁₂H₁₅BrO₂
• 分子量: 271.154
• InChiKey: ZDRNFELUUSAYKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-5-isopropoxy-4-methoxystyrene 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以77%的产率得到2-(2-bromo-5-isopropoxy-4-methoxyphenyl)ethanol
  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 、 甲基三苯基溴化膦 在 sodium hydride 、 二甲基亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以81%的产率得到2-bromo-5-isopropoxy-4-methoxystyrene
  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.