(R,E)-methyl 5-(bromo(4-chlorophenyl)methylene)-3-(3-(4-chlorophenyl)prop-2-yn-1-yl)-2-oxotetrahydrofuran-3-carboxylate | 1436871-98-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (R,E)-methyl 5-(bromo(4-chlorophenyl)methylene)-3-(3-(4-chlorophenyl)prop-2-yn-1-yl)-2-oxotetrahydrofuran-3-carboxylate
• 英文别名: methyl (3R,5E)-5-[bromo-(4-chlorophenyl)methylidene]-3-[3-(4-chlorophenyl)prop-2-ynyl]-2-oxooxolane-3-carboxylate
• CAS: 1436871-98-5
• 化学式: C₂₂H₁₅BrCl₂O₄
• 分子量: 494.169
• InChiKey: OWFDWDDIYZQOBU-ZSVKVYQISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二甲基-2.2-二(丙-2-炔基)丙二酸二乙酯 在 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 Hydroquinone 1,4-phthalazinediyl diether 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 为溶剂， 反应 15.25h， 生成 (R,E)-methyl 5-(bromo(4-chlorophenyl)methylene)-3-(3-(4-chlorophenyl)prop-2-yn-1-yl)-2-oxotetrahydrofuran-3-carboxylate
  参考文献：
  名称：

  Enantioselective, Desymmetrizing Bromolactonization of Alkynes

  摘要：

  Asymmetric bromolactonizations of alkynes are possible using a desymmetrization approach. The commercially available catalyst (DHQD)(2)PHAL promotes these cyclizations in combination with cheap NBS as a bromine source to give bromoenol lactones in high yield and with high enantioselectivity. The bromoenol lactone products, containing a tetrasubstituted alkene and a quaternary stereocenter are valuable building blocks for synthetic chemistry.

  DOI：

  10.1021/ja402910d

文献信息

• Enantioselective, Desymmetrizing Bromolactonization of Alkynes
  作者：Michael Wilking、Christian Mück-Lichtenfeld、Constantin G. Daniliuc、Ulrich Hennecke

  DOI：10.1021/ja402910d

  日期：2013.6.5

  Asymmetric bromolactonizations of alkynes are possible using a desymmetrization approach. The commercially available catalyst (DHQD)(2)PHAL promotes these cyclizations in combination with cheap NBS as a bromine source to give bromoenol lactones in high yield and with high enantioselectivity. The bromoenol lactone products, containing a tetrasubstituted alkene and a quaternary stereocenter are valuable building blocks for synthetic chemistry.