3-butynyl formate | 111515-60-7

• 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: 3-butynyl formate
• 英文别名: 3-(1-Butynyl) formate；But-3-ynyl formate
• CAS: 111515-60-7
• 化学式: C₅H₆O₂
• 分子量: 98.1014
• InChiKey: IVIYCMOSYIUWJH-UHFFFAOYSA-N

物化性质

• 沸点：
  124 °C(Press: 660 Torr)
• 密度：
  0.995±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  3-butynyl formate 在 十二羰基三钌 甲酸 作用下， 反应 3.0h， 生成 3-氧代丁基甲酸酯
  参考文献：
  名称：

  Hydration of alkynes in anhydrous medium with formic acid as water donor

  摘要：

  Formic acid has been found to hydrate alkynes in the absence of water to give oxo products and carbon monoxide. The scope of the reaction of alkynes and formic acid has been delineated. Hydrocarbon alkynes were found to be reactive in the absence of catalyst. Functionalized alkynes, in particular oxygenated alkynes, are inert toward formic acid but can be activated catalytically with Ru3(CO)12. Consequently, all the tested types of alkynes were found to give oxo products and CO with formic acid. The mechanism of the reaction was examined. With some alkynes, the primary oxo products underwent secondary reactions that gave rise to unexpected products.

  DOI：

  10.1021/jo00078a023
• 作为产物：
  描述：

  甲酸 、 3-丁炔-1-醇 反应 0.25h， 生成 3-butynyl formate
  参考文献：
  名称：

  Hydration of alkynes in anhydrous medium with formic acid as water donor

  摘要：

  Formic acid has been found to hydrate alkynes in the absence of water to give oxo products and carbon monoxide. The scope of the reaction of alkynes and formic acid has been delineated. Hydrocarbon alkynes were found to be reactive in the absence of catalyst. Functionalized alkynes, in particular oxygenated alkynes, are inert toward formic acid but can be activated catalytically with Ru3(CO)12. Consequently, all the tested types of alkynes were found to give oxo products and CO with formic acid. The mechanism of the reaction was examined. With some alkynes, the primary oxo products underwent secondary reactions that gave rise to unexpected products.

  DOI：

  10.1021/jo00078a023

文献信息

• C-H rather than O–H activation: synthesis and molecular structure of a cationic cis-hydrido-σ-acetylide complex of rhodium
  作者：Todd B. Marder、David Zargarian、Joseph C. Calabrese、Thomas H. Herskovitz、David Milstein

  DOI：10.1039/c39870001484

  日期：——

  Terminal alkynes, including those with acidic O–H groups, react with [Rh(PMe3)4]Cl in tetrahydrofuran (THF) or in water yielding cis-hydrido-σ-acetylide complexes via C-H activation; the molecular structure of cis-[Rh(PMe3)4(H)(CC–CH2OH)]Cl has been determined by X-ray diffraction.

  末端炔烃，包括带有酸性OH基团的炔烃，在四氢呋喃（THF）或水中与[Rh（PMe 3）4 ] Cl反应，通过CH活化生成顺式-氢化-σ-乙炔化物络合物；X射线衍射法测定了顺式-[Rh（PMe 3）4（H）（C C–CH 2 OH）] Cl的分子结构。
• Carlson, Charles G.; Hall, Judith E.; Huang, Yan Y., Canadian Journal of Chemistry, 1987, vol. 65, p. 2461 - 2463
  作者：Carlson, Charles G.、Hall, Judith E.、Huang, Yan Y.、Kotila, Sirpa、Rauk, Arvi、Tavares, Donald F.

  DOI：——

  日期：——
• CARLSON, CHARLES G.;HALL, JUDITH E.;HUANG, YAN. Y.;KOTILA, SIRPA;RAUK, AR+, CAN. J. CHEM., 65,(1987) N 10, 2461-2463
  作者：CARLSON, CHARLES G.、HALL, JUDITH E.、HUANG, YAN. Y.、KOTILA, SIRPA、RAUK, AR+

  DOI：——

  日期：——