Ethyl 2-(4-hydroxybutyl)-2-cyclopropene-1-carboxylate | 362681-36-5

• 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-(4-hydroxybutyl)-2-cyclopropene-1-carboxylate
• 英文别名: Ethyl 2-(4-hydroxybutyl)cycloprop-2-ene-1-carboxylate；ethyl 2-(4-hydroxybutyl)cycloprop-2-ene-1-carboxylate
• CAS: 362681-36-5
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: RMLQWACRMKIURW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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-(4-hydroxybutyl)-2-cyclopropene-1-carboxylate 在 吡啶 、 indium 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 2-Acetoxymethyl-1-(4-acetoxybutyl)-1-allylcyclopropane
  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：

  5-hexyn-1-yl acetate 在 dirhodium tetraacetate potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 Ethyl 2-(4-hydroxybutyl)-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

• 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.