(R,E)-4,4'-(penta-1,4-diene-1,3-diyl)bis(methoxybenzene) | 1418147-90-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (R,E)-4,4'-(penta-1,4-diene-1,3-diyl)bis(methoxybenzene)
• 英文别名: 1-methoxy-4-[(1E,3R)-1-(4-methoxyphenyl)penta-1,4-dien-3-yl]benzene
• CAS: 1418147-90-6
• 化学式: C₁₉H₂₀O₂
• 分子量: 280.367
• InChiKey: JFPWOMOGZNTYSH-CDVVCGDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 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：

  (R,E)-4,4'-(penta-1,4-diene-1,3-diyl)bis(methoxybenzene) 在 甲基碘化镁 作用下， 以 乙醚 为溶剂， 160.0 ℃ 、20.0 kPa 条件下， 反应 1.0h， 以86%的产率得到(+)-(7R,E)-hinokiresinol
  参考文献：
  名称：

  Iridium-Catalyzed Enantioselective Allylic Vinylation

  摘要：

  The first example of Ir-catalyzed asymmetric substitution reaction with vinyl trifluoroborates is described. The direct reaction between branched, racemic allylic alcohols and potassium alkenyltrifluoroborates proceeded with high site selectivity and excellent enantioselectivity (up to 99%) mediated by an Ir-(P,olefin) complex. This method allows rapid access to various 1,4-dienes or trienes including the biologically active natural products (-)-nyasol and (-)-hinokiresinol.

  DOI：

  10.1021/ja311422z
• 作为产物：
  描述：

  potassium (E)-trifluoro(4-methoxystyryl)borate 、 1'-羟基草蒿脑 在 5-((11bS)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-yl)-5H-dibenzo[b,f]azepine 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 氢氟酸 、 四丁基硫酸氢铵 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 4.0h， 以94%的产率得到
  参考文献：
  名称：

  Iridium-Catalyzed Enantioselective Allylic Vinylation

  摘要：

  The first example of Ir-catalyzed asymmetric substitution reaction with vinyl trifluoroborates is described. The direct reaction between branched, racemic allylic alcohols and potassium alkenyltrifluoroborates proceeded with high site selectivity and excellent enantioselectivity (up to 99%) mediated by an Ir-(P,olefin) complex. This method allows rapid access to various 1,4-dienes or trienes including the biologically active natural products (-)-nyasol and (-)-hinokiresinol.

  DOI：

  10.1021/ja311422z

文献信息

• Iridium-Catalyzed Enantioselective Allylic Vinylation
  作者：James Y. Hamilton、David Sarlah、Erick M. Carreira

  DOI：10.1021/ja311422z

  日期：2013.1.23

  The first example of Ir-catalyzed asymmetric substitution reaction with vinyl trifluoroborates is described. The direct reaction between branched, racemic allylic alcohols and potassium alkenyltrifluoroborates proceeded with high site selectivity and excellent enantioselectivity (up to 99%) mediated by an Ir-(P,olefin) complex. This method allows rapid access to various 1,4-dienes or trienes including the biologically active natural products (-)-nyasol and (-)-hinokiresinol.