(E)-4-(4-(naphthalen-3-yl)but-2-en-1-yl)-3,6-dihydro-2H-pyran | 1427271-57-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-4-(4-(naphthalen-3-yl)but-2-en-1-yl)-3,6-dihydro-2H-pyran
• 英文别名: 4-[(E)-4-naphthalen-2-ylbut-2-enyl]-3,6-dihydro-2H-pyran
• CAS: 1427271-57-5
• 化学式: C₁₉H₂₀O
• 分子量: 264.367
• InChiKey: NKSMHEJPSRGIQB-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-萘硼酸 、 1,3-丁二烯 、 3,6-二氢-2H-吡喃-4-三氟甲烷磺酸盐 在 potassium fluoride 、 tris-(dibenzylideneacetone)dipalladium(0) 作用下， 以 正己烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 16.0h， 以86%的产率得到
  参考文献：
  名称：

  Palladium-Catalyzed 1,4-Difunctionalization of Butadiene To Form Skipped Polyenes

  摘要：

  A palladium-catalyzed 1,4-addition across the commodity chemical 1,3-butadiene to afford skipped polyene products is reported. Through a palladium sigma -> pi -> sigma allyl isomerization, two new carbon-carbon bonds are formed with high regioselectivity and trans stereoselectivity of the newly formed alkene. The utility of this method is highlighted by the successful synthesis of the ripostatin A skipped triene core.

  DOI：

  10.1021/ja3110544

文献信息

• Palladium-Catalyzed 1,4-Difunctionalization of Butadiene To Form Skipped Polyenes
  作者：Matthew S. McCammant、Longyan Liao、Matthew S. Sigman

  DOI：10.1021/ja3110544

  日期：2013.3.20

  A palladium-catalyzed 1,4-addition across the commodity chemical 1,3-butadiene to afford skipped polyene products is reported. Through a palladium sigma -> pi -> sigma allyl isomerization, two new carbon-carbon bonds are formed with high regioselectivity and trans stereoselectivity of the newly formed alkene. The utility of this method is highlighted by the successful synthesis of the ripostatin A skipped triene core.