Ethyl 2-(3-hydroxypropyl)-2-cyclopropene-1-carboxylate | 362681-35-4

• 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-(3-hydroxypropyl)-2-cyclopropene-1-carboxylate
• 英文别名: Ethyl 2-(3-hydroxypropyl)cycloprop-2-ene-1-carboxylate；ethyl 2-(3-hydroxypropyl)cycloprop-2-ene-1-carboxylate
• CAS: 362681-35-4
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: NTHIOAVPUJIHND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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-(3-hydroxypropyl)-2-cyclopropene-1-carboxylate 在 吡啶 、 indium 、 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 2-Acetoxymethyl-1-(3-acetoxypropyl)-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：

  乙酸4-炔酯 在 dirhodium tetraacetate potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 Ethyl 2-(3-hydroxypropyl)-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

• Cis double allylation of cyclopropenes using cyclopropylindium reagents
  作者：Tsunehisa Hirashita、Fumio Shiraki、Kenji Onishi、Mamiko Ogura、Shuki Araki

  DOI：10.1039/b706539f

  日期：——

  The successive double allylation of cyclopropenes with allylindium sesquiiodide and allyl iodide proceeded with a cis-addition mode in the presence of other organometallics (e.g. Grignard reagent, cuprate, Et2Zn and Et3Al), giving the corresponding cis-diallylcyclopropanes in high yields.

  环丙烯与三碘化铟烯和烯丙基碘的连续双烯丙基化反应在其他有机金属化合物（如格里尼亚试剂、铜盐、二乙基锌和三乙基铝）的存在下以顺式加成模式进行，获得了高产率的相应顺式双烯丙基环丙烷。