(Z)-1,4-Bis((2-bromo-4,5-(methylenedioxy)phenyl)methoxy)-2-butene | 161720-73-6

• 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: (Z)-1,4-Bis((2-bromo-4,5-(methylenedioxy)phenyl)methoxy)-2-butene
• 英文别名: (Z)-1,4-Bis{[2-bromo-4,5-(methylenedioxy)phenyl]methoxy}-2-butene；5-bromo-6-[[(Z)-4-[(6-bromo-1,3-benzodioxol-5-yl)methoxy]but-2-enoxy]methyl]-1,3-benzodioxole
• CAS: 161720-73-6
• 化学式: C₂₀H₁₈Br₂O₆
• 分子量: 514.167
• InChiKey: NMYABTKZUYWQGX-UPHRSURJSA-N

物化性质

• 沸点：
  569.9±50.0 °C(predicted)
• 密度：
  1.658±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-1,4-Bis((2-bromo-4,5-(methylenedioxy)phenyl)methoxy)-2-butene 在 sodium periodate 、 四氧化锇 、 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 以78%的产率得到2-((2-Bromo-4,5-(methylenedioxy)phenyl)methoxy)ethanal
  参考文献：
  名称：

  Palladium-Promoted Intramolecular Addition of an Aryl Iodide to a Nitroalkene

  摘要：

  Iodoaryl nitroalkene 9 was found to undergo a palladium-promoted Heck cyclization in the presence of Pd(OAc)(2) (1.0 equiv), triphenylphosphine (2.0 equiv), and Ag2CO3 (2.0 equiv) in benzene at 25 degrees C to afford exocyclic 2,2-disubstituted-1-nitroalkene (Z)-2 as a single geometrical isomer (43%) along with the corresponding saturated nitroalkane 10 (40%). Subsequent selenylation of the nitroalkane, oxidative elimination, and olefin isomerization afforded (Z)-2 in 70% yield. The influence of Ag2CO3 and solvent on the cyclization and the mechanism of nitroalkane formation are proposed.

  DOI：

  10.1021/jo00109a037
• 作为产物：
  描述：

  5-溴-6-溴甲基-1,3-苯并二氧杂环戊二烯 、 顺式-1,2-二羟甲基乙烯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到(Z)-1,4-Bis((2-bromo-4,5-(methylenedioxy)phenyl)methoxy)-2-butene
  参考文献：
  名称：

  Palladium-Promoted Intramolecular Addition of an Aryl Iodide to a Nitroalkene

  摘要：

  Iodoaryl nitroalkene 9 was found to undergo a palladium-promoted Heck cyclization in the presence of Pd(OAc)(2) (1.0 equiv), triphenylphosphine (2.0 equiv), and Ag2CO3 (2.0 equiv) in benzene at 25 degrees C to afford exocyclic 2,2-disubstituted-1-nitroalkene (Z)-2 as a single geometrical isomer (43%) along with the corresponding saturated nitroalkane 10 (40%). Subsequent selenylation of the nitroalkane, oxidative elimination, and olefin isomerization afforded (Z)-2 in 70% yield. The influence of Ag2CO3 and solvent on the cyclization and the mechanism of nitroalkane formation are proposed.

  DOI：

  10.1021/jo00109a037

文献信息

• Palladium-Promoted Intramolecular Addition of an Aryl Iodide to a Nitroalkene
  作者：Scott E. Denmark、Mark E. Schnute

  DOI：10.1021/jo00109a037

  日期：1995.2

  Iodoaryl nitroalkene 9 was found to undergo a palladium-promoted Heck cyclization in the presence of Pd(OAc)(2) (1.0 equiv), triphenylphosphine (2.0 equiv), and Ag2CO3 (2.0 equiv) in benzene at 25 degrees C to afford exocyclic 2,2-disubstituted-1-nitroalkene (Z)-2 as a single geometrical isomer (43%) along with the corresponding saturated nitroalkane 10 (40%). Subsequent selenylation of the nitroalkane, oxidative elimination, and olefin isomerization afforded (Z)-2 in 70% yield. The influence of Ag2CO3 and solvent on the cyclization and the mechanism of nitroalkane formation are proposed.