Ethyl 2-(2-hydroxyethyl)-2-cyclopropene-1-carboxylate | 362681-34-3

• 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: Ethyl 2-(2-hydroxyethyl)-2-cyclopropene-1-carboxylate
• 英文别名: ethyl 2-(2-hydroxyethyl)cycloprop-2-ene-1-carboxylate
• CAS: 362681-34-3
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: RHUJWVYOEOYRJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 2-(2-hydroxyethyl)-2-cyclopropene-1-carboxylate 在 吡啶 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 3-(Acetoxymethyl)-1-(2-acetoxyethyl)cyclopropene
  参考文献：
  名称：

  Allylindation of Cyclopropenes in Organic and Aqueous Media: Switching the Regio- and Stereoselectivity Based on the Chelation with a Hydroxyl Group and the Crystal Structure of the Cyclopropylindium Product

  摘要：

  Hydroxy-bearing cyclopropenes react with allylindium reagents to undergo clean allylindation both in organic and aqueous media, in which the chelation of the hydroxyl group to indium plays the central role. The regio-and stereoselectivity have been regulated both by the location of the hydroxyl group in the molecules and the reaction solvents. In particular, the allylindation in water shows marked differences from that in organic solvents; the regio- and stereoselectivity have totally been reversed compared with those in organic solvents. Unusually stable cyclopropylindium compounds have been isolated from the reaction of 1-(omega -hydroxyalkyl)-cyclopropenes and the structure has fully been established by X-ray crystallography.

  DOI：

  10.1002/1521-3765(20010702)7:13<2784::aid-chem2784>3.0.co;2-a
• 作为产物：
  描述：

  Ethyl 2-(2-acetoxyethyl)-2-cyclopropene-1-carboxylate 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 70.0h， 以52%的产率得到Ethyl 2-(2-hydroxyethyl)-2-cyclopropene-1-carboxylate
  参考文献：
  名称：

  Allylindation of Cyclopropenes in Organic and Aqueous Media: Switching the Regio- and Stereoselectivity Based on the Chelation with a Hydroxyl Group and the Crystal Structure of the Cyclopropylindium Product

  摘要：

  Hydroxy-bearing cyclopropenes react with allylindium reagents to undergo clean allylindation both in organic and aqueous media, in which the chelation of the hydroxyl group to indium plays the central role. The regio-and stereoselectivity have been regulated both by the location of the hydroxyl group in the molecules and the reaction solvents. In particular, the allylindation in water shows marked differences from that in organic solvents; the regio- and stereoselectivity have totally been reversed compared with those in organic solvents. Unusually stable cyclopropylindium compounds have been isolated from the reaction of 1-(omega -hydroxyalkyl)-cyclopropenes and the structure has fully been established by X-ray crystallography.

  DOI：

  10.1002/1521-3765(20010702)7:13<2784::aid-chem2784>3.0.co;2-a

文献信息

• Radical Homopolymerization of Linear α‐Olefins Enabled by 1,4‐Cyano Group Migration
  作者：Bang An、Litao Zhou、Shuai Liu、Yaxin Zheng、Changhu Li、Feichen Cui、Chaowei Yue、Hua Liu、Yang Sui、Chonglei Ji、Jiajun Yan、yifan li

  DOI：10.1002/anie.202402511

  日期：——

  Radical homopolymerization of linear α-olefins has been developed. The success of this polymerization relies on the high efficiency of 1,4-cyano group migration. This approach can be applied to homopolymerize α- substituted styrenes or acrylates. As a chain transfer agent, a symmetric allylic sulfide is created to regulate the propagating thiyl radicals over the polymerization process.

  线性α-烯烃的自由基均聚已被开发出来。该聚合的成功依赖于1,4-氰基迁移的高效率。该方法可用于均聚α-取代苯乙烯或丙烯酸酯。作为链转移剂，产生对称烯丙基硫醚来调节聚合过程中的硫基自由基的增长。
• Allylindation of Cyclopropenes in Organic and Aqueous Media: Switching the Regio- and Stereoselectivity Based on the Chelation with a Hydroxyl Group and the Crystal Structure of the Cyclopropylindium Product
  作者：Shuki Araki、Fumio Shiraki、Takashi Tanaka、Hiroyuki Nakano、Kandasamy Subburaj、Tsunehisa Hirashita、Hatsuo Yamamura、Masao Kawai

  DOI：10.1002/1521-3765(20010702)7:13<2784::aid-chem2784>3.0.co;2-a

  日期：2001.7.2

  Hydroxy-bearing cyclopropenes react with allylindium reagents to undergo clean allylindation both in organic and aqueous media, in which the chelation of the hydroxyl group to indium plays the central role. The regio-and stereoselectivity have been regulated both by the location of the hydroxyl group in the molecules and the reaction solvents. In particular, the allylindation in water shows marked differences from that in organic solvents; the regio- and stereoselectivity have totally been reversed compared with those in organic solvents. Unusually stable cyclopropylindium compounds have been isolated from the reaction of 1-(omega -hydroxyalkyl)-cyclopropenes and the structure has fully been established by X-ray crystallography.