epoxybutyne | 6924-81-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: epoxybutyne
• 英文别名: epoxy-3,4 butyne-1；2-ethynyloxirane；Epoxybutin；3,4-Epoxybutin-1；3,4-epoxy-but-1-yne；3,4-Epoxy-but-1-in；ethynyl-oxirane
• CAS: 6924-81-8
• 化学式: C₄H₄O
• 分子量: 68.0752
• InChiKey: WYFBDQAYFMKCER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  5
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  epoxybutyne 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 4.0h， 以85%的产率得到but-3-yne-1,2-diol
  参考文献：
  名称：

  乙烯基和烯丙基乙炔的次卤代化和产物的一些化学转化

  摘要：

  Hypohalogenation of 2-methylhex-5-en-3-yn-2-ol, 2-methylhept-6-en-3-yn-2-ol, and their methyl ethers at 303-328 K with hydrochloric or hydrobromic acid in the presence of hydrogen peroxide involves only the double bond to produce the corresponding halohydrins in fairly high yields. Kinetic parameters of these reactions were determined, and the allylacetylenic alcohol and its methyl ether were found to be more reactive than their vinylacetylenic analogs. Acetylenic halohydrins and oxiranes derived therefrom were shown to be quite reactive compounds which may be used as building blocks in organic synthesis.

  DOI：

  10.1134/s1070428007110036
• 作为产物：
  描述：

  2-methyl-4-(oxiran-2-yl)but-3-yn-2-ol 在 氢氧化钾 作用下， 以87%的产率得到epoxybutyne
  参考文献：
  名称：

  乙烯基和烯丙基乙炔的次卤代化和产物的一些化学转化

  摘要：

  Hypohalogenation of 2-methylhex-5-en-3-yn-2-ol, 2-methylhept-6-en-3-yn-2-ol, and their methyl ethers at 303-328 K with hydrochloric or hydrobromic acid in the presence of hydrogen peroxide involves only the double bond to produce the corresponding halohydrins in fairly high yields. Kinetic parameters of these reactions were determined, and the allylacetylenic alcohol and its methyl ether were found to be more reactive than their vinylacetylenic analogs. Acetylenic halohydrins and oxiranes derived therefrom were shown to be quite reactive compounds which may be used as building blocks in organic synthesis.

  DOI：

  10.1134/s1070428007110036

文献信息

• Enzymatic kinetic resolution of primary allenic alcohols. Application to the total synthesis and stereochemical assignment of striatisporolide A
  作者：Jan Deska、Jan-E. Bäckvall

  DOI：10.1039/b912128p

  日期：——

  Crude Porcine pancreatic lipase was successfully used for the kinetic resolution of axially chiral primary allenic alcohols providing very high enantioselectivities with E values above 200. This simple access to optically active allenes was applied to the total synthesis of the fungal metabolite (−)-striatisporolide A, allowing its unambiguous stereochemical assignment.

  粗猪胰脂肪酶已成功用于轴向手性伯烯丙醇的动力学拆分，提供了非常高的对映选择性，E值大于200。这种简单的旋光性丙二烯的获取方法可用于真菌代谢产物的全合成（-）-三甲酚内酯A，使其具有明确的立体化学分配。
• Golodova,K.G.; Yakimovich,S.I., Journal of Organic Chemistry USSR (English Translation), 1972, vol. 8, p. 2530 - 2536
  作者：Golodova,K.G.、Yakimovich,S.I.

  DOI：——

  日期：——
• Beny, Jean-Pierre; Pommelet, Jean-Claude; Chuche, Josselin, Bulletin de la Societe Chimique de France, 1981, vol. 2, # 9-10, p. 377 - 386
  作者：Beny, Jean-Pierre、Pommelet, Jean-Claude、Chuche, Josselin

  DOI：——

  日期：——
• Lespieau, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1925, vol. 180, p. 442
  作者：Lespieau

  DOI：——

  日期：——
• Kleijn, H.; Meijer, J.; Overbeek, G. C., Recueil des Travaux Chimiques des Pays-Bas, 1982, vol. 101, # 3, p. 97 - 101
  作者：Kleijn, H.、Meijer, J.、Overbeek, G. C.、Vermeer. P.

  DOI：——

  日期：——