exo-acrylic acid bicyclo[2.2.1]hept-2-yl ester

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: exo-acrylic acid bicyclo[2.2.1]hept-2-yl ester
• 英文别名: 2-exo-bicyclo[2.2.1]heptyl acrylate；[(1R,2R,4S)-2-bicyclo[2.2.1]heptanyl] prop-2-enoate
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: IQYMRQZTDOLQHC-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  exo-acrylic acid bicyclo[2.2.1]hept-2-yl ester 在 Ni on Kieselguhr sodium hydroxide 、 氢气 、 对苯二酚 作用下， 以 乙醇 为溶剂， 70.0~120.0 ℃ 、10.13 MPa 条件下， 反应 4.5h， 生成 exo-2-norbornanol
  参考文献：
  名称：

  摘要：

  A simple and more environmentally friendly procedure than that traditionally used was developed for preparation of esters consisting in acrylic acid addition to bicyclo[2.2.1]hept-2-ene and its 5-alkyl derivatives. The acrylates obtained were subjected to hydrogenetion followed by hydrolysis of propionic acid esters. A number of new compounds was obtained; some among them possess a pleasant odor.

  DOI：

  10.1023/a:1013961731999
• 作为产物：
  描述：

  norbornene 、 丙烯酸 在 iron(III) trifluoromethanesulfonate 作用下， 以 二丁醚 为溶剂， 反应 18.0h， 以99%的产率得到exo-acrylic acid bicyclo[2.2.1]hept-2-yl ester
  参考文献：
  名称：

  Iron-catalysed green synthesis of carboxylic esters by the intermolecular addition of carboxylic acids to alkenes

  摘要：

  三氟甲磺酸铁，由FeCl3和三氟甲磺酸或FeCl3和银三氟甲磺酸盐原位形成，能高效催化羧酸对各种烯烃的分子间加成反应，生成羧酸酯；该反应适用于合成不稳定酯类，如丙烯酸酯。

  DOI：

  10.1039/b713951a

文献信息

• Iron-catalysed green synthesis of carboxylic esters by the intermolecular addition of carboxylic acids to alkenes
  作者：Jun-Chul Choi、Kazufumi Kohno、Daisuke Masuda、Hiroyuki Yasuda、Toshiyasu Sakakura

  DOI：10.1039/b713951a

  日期：——

  Iron triflate, in situ-formed from FeCl3 and triflic acid, or FeCl3 and silver triflate efficiently catalyse the intermolecular addition of carboxylic acids to various alkenes to yield carboxylic esters; the reaction is applicable to the synthesis of unstable esters, such as acrylates.

  三氟甲磺酸铁，由FeCl3和三氟甲磺酸或FeCl3和银三氟甲磺酸盐原位形成，能高效催化羧酸对各种烯烃的分子间加成反应，生成羧酸酯；该反应适用于合成不稳定酯类，如丙烯酸酯。
• Oxidative Alkenylation/Annulation of Benzimidates<i>via</i>Ruthenium(II)-Catalyzed CH Activation to Generate 3-Methyleneisoindolin-1-ones
  作者：Xing Guang Li、Min Sun、Kai Liu、Pei Nian Liu

  DOI：10.1002/adsc.201400727

  日期：2015.2.9

  AbstractA novel ruthenium‐catalyzed oxidative alkenylation/annulation cascade reaction is described for synthesizing 3‐methyleneisoindolin‐1‐ones. In the protocol, the NH imidate is applied efficiently as a directing group in ruthenium‐catalyzed CH activation, generating various 3‐methyleneisoindolin‐1‐ones with high regio‐ and stereoselectivity in moderate to good yields.magnified image
• ——
  作者：M. K. Mamedov、E. K. Nabieva、E. N. Dzhafarova

  DOI：10.1023/a:1013961731999

  日期：——

  A simple and more environmentally friendly procedure than that traditionally used was developed for preparation of esters consisting in acrylic acid addition to bicyclo[2.2.1]hept-2-ene and its 5-alkyl derivatives. The acrylates obtained were subjected to hydrogenetion followed by hydrolysis of propionic acid esters. A number of new compounds was obtained; some among them possess a pleasant odor.
• Synthesis of bi- and tricyclic acrylates in the presence of boron trifluoride etherate
  作者：M. K. Mamedov、R. A. Rasulova

  DOI：10.1134/s1070428010050039

  日期：2010.5

  The addition of acrylic acid to bicyclo[2.2.1]heptene hydrocarbons and tricyclo[5.2.1.0(2,6)]deca-3,8-diene catalyzed with BF(3)center dot O(C(2)H(5))(2) was studied and bi- and tricyclic esters of acrylic acid were synthesized that were reactive monomers for preparation of macromolecular compounds.