endo-2-butoxycarbonyl-5-norbornene

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: endo-2-butoxycarbonyl-5-norbornene
• 英文别名: butyl (1R,2R,4R)-bicyclo[2.2.1]hept-5-ene-2-carboxylate
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: RFIHUFUZAHTZOQ-OUAUKWLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  丙烯酸丁酯 、 环戊二烯 在 果糖 、 N,N-二甲基脲 作用下， 生成 exo-2-butoxycarbonyl-5-norbornene 、 endo-2-butoxycarbonyl-5-norbornene
  参考文献：
  名称：

  Low-melting sugar–urea–salt mixtures as solvents for Diels–Alder reactions

  摘要：

  将简单碳水化合物、尿素和无机盐的混合物加热至中等温度，即可获得甜味溶液，为有机反应提供新的手性介质。

  DOI：

  10.1039/b414515a

文献信息

• Diels–Alder Reaction of Cyclopentadiene and Alkyl Acrylates in the Presence of Pyrrolidinium Ionic Liquids with Various Anions
  作者：Waldemar Stefaniak、Ewa Janus、Eugeniusz Milchert

  DOI：10.1007/s10562-011-0558-6

  日期：2011.5

  The conversion and stereoselectivity of transformation to endo and exo norbornene derivatives was determined in the Diels-Alder reaction of cyclopentadiene with alkyl acrylates. The reactions were carried out in the pyrrolidinium ionic liquids in the presence of metal chlorides and trifluoromethanesulfonates as the catalysts. Shorter reaction times and higher conversions of dienophile were observed in a comparison with analogous cycloadditions carried out in the presence of conventional organic solvents. A higher stereoselectivity to the endo isomer was found in the majority of cases. The ionic liquids composed of 1-butyl-1-methylpyrrolidinium cation (Pyrr(1.4)) and various anions were used. The influence of ionic liquid anion and several metal chlorides and metal triflates used as the catalysts on the conversion was determined.
• Triethylsulfonium Bistriflimide as the Reaction Medium in Catalyzed and Uncatalyzed Cycloaddition [4 + 2]
  作者：Ewa Janus、Bożena Bittner

  DOI：10.1007/s10562-009-0211-9

  日期：2010.1

  Triethylsulfonium bistriflimide, [S-2.2.2][NTf2], has been tested and compared with other ionic liquids and molecular solvents as a medium in Diels-Alder reaction between cyclopentadiene and dimethyl maleate. Triflates and chlorides of different metals have been combined with [S-2.2.2][NTf2] and the catalytic activity of the systems formed have been determined. The effect of concentration of the catalysts in sulfonium ionic liquid and reactants on the yield and endo:exo ratio has been established. The representative catalyst-Yb(OTf)(3)center dot xH(2)O in [S-2.2.2][NTf2] has been examined in the reaction of cyclopentadiene with various dienophiles. The use of sulfonium ionic liquids permitted recycling the catalysts. For the best four catalytic systems, the products have been isolated.
• Oakes, R. Scott; Heppenstall, Toby J.; Shezad, Najam, Chemical Communications, 1999, # 16, p. 1459 - 1460
  作者：Oakes, R. Scott、Heppenstall, Toby J.、Shezad, Najam、Clifford, Anthony A.、Rayner, Christopher M.

  DOI：——

  日期：——