2-(prop-2-yn-1-yl)oxirane | 59627-27-9

• 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: 2-(prop-2-yn-1-yl)oxirane
• 英文别名: -ethylenoxid；prop-2-ynyl-oxirane；Propargyloxirane；2-prop-2-ynyloxirane
• CAS: 59627-27-9
• 化学式: C₅H₆O
• 分子量: 82.102
• InChiKey: OVSJEFPNKYVHJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  2-(prop-2-yn-1-yl)oxirane 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 4.0h， 以90%的产率得到戊-4-炔-1,2-二醇
  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-5-(oxiran-2-yl)pent-3-yn-2-ol 在 氢氧化钾 作用下， 以89%的产率得到2-(prop-2-yn-1-yl)oxirane
  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

• Synthesis and dopaminergic activity of 3-substituted 1-(aminomethyl)-3,4-dihydro-5,6-dihydroxy-1H-2-benzopyrans: characterization of an auxiliary binding region in the D1 receptor
  作者：Michael P. DeNinno、Robert Schoenleber、Richard J. Perner、Linda Lijewski、Karen E. Asin、Donald R. Britton、Robert MacKenzie、John W. Kebabian

  DOI：10.1021/jm00112a034

  日期：1991.8

  The synthesis and dopaminergic activity of a series of C3 and nitrogen-substituted 1-(aminomethyl)-3,4-dihydro-5,6-dihydroxy-1H-2-benzopyrans (isochromans) is described. The synthesis of the compounds was stereospecific for the 1,3 cis isomer, and the enantioselective synthesis of both enantiomers of one of the analogoues (20) was achieved. It was determined that all of the dopaminergic activity resides in the [1R,3S] isomer. Generally, substitution at the C3 position provided compounds with very high potency (< 10 nm EC50) and selectivity for the D1 receptor, with a wide range of intrinsic activities (60-160%). Analogues containing C3 substituents including aryl, arylalkyl, and cyclic and acyclic alkyl groups showed a marked enhancement of dopaminergic activity compared to the unsubstituted compound. As a class, the drugs were orally active in the rat rotation model with a very long duration of action.
• SCHREURS P. H. M.; JONG A. J. DE; BRANDSMA L., REC. TRAV. CHIM. <RTCP-A3>, 1976, 95, NO 4, 75-78
  作者：SCHREURS P. H. M.、 JONG A. J. DE、 BRANDSMA L.

  DOI：——

  日期：——
• Hypohalogenation of vinyl- and allylacetylenes and some chemical transformations of the products
  作者：M. G. Veliev、O. A. Sadygov、Kh. M. Alimardanov、M. I. Shatirova

  DOI：10.1134/s1070428007110036

  日期：2007.11

  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.