2-{[(3-phenylprop-2-ynyl)oxy]methyl}oxiran | 42468-63-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-{[(3-phenylprop-2-ynyl)oxy]methyl}oxiran
• 英文别名: (3-phenyl-prop-2-ynyloxymethyl)-oxirane；2-{[(3-Phenylprop-2-yn-1-yl)oxy]methyl}oxirane；2-(3-phenylprop-2-ynoxymethyl)oxirane
• CAS: 42468-63-3
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: LIHPMMGNQGWPDD-UHFFFAOYSA-N

物化性质

• 沸点：
  311.7±22.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  21.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-{[(3-phenylprop-2-ynyl)oxy]methyl}oxiran 在 bis(1,5-cyclooctadiene)nickel (0) 、 三乙基硼 、 三丁基膦 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以50%的产率得到(5Z)-5-benzylidenetetrahydro-2H-pyran-3-ol
  参考文献：
  名称：

  Nickel-Catalyzed Reductive Coupling of Alkynes and Epoxides

  摘要：

  Nickel-catalyzed, intramolecular and intermolecular reductive coupling of alkynes and epoxides affords synthetically useful homoallylic alcohols of defined alkene geometry. Very high regioselectivity is generally observed, and cyclizations proceed with complete selectivity for endo epoxide opening. This catalytic reaction represents the first use of a non-pi-based electrophile in a growing class of nickel-catalyzed, multicomponent coupling reactions, and is the first catalytic method of reductive coupling of alkynes and epoxides that is effective for both intermolecular and intramolecular cases, and mechanistically distinct from these, possibly involving a nickella(II)oxetane.

  DOI：

  10.1021/ja0361401
• 作为产物：
  描述：

  3-苯基-2-丙炔-1-醇 、 环氧氯丙烷 在 sodium hydroxide 、 四丁基硫酸氢铵 、 臭氧 作用下， 以71%的产率得到2-{[(3-phenylprop-2-ynyl)oxy]methyl}oxiran
  参考文献：
  名称：

  Nickel-Catalyzed Reductive Coupling of Alkynes and Epoxides

  摘要：

  Nickel-catalyzed, intramolecular and intermolecular reductive coupling of alkynes and epoxides affords synthetically useful homoallylic alcohols of defined alkene geometry. Very high regioselectivity is generally observed, and cyclizations proceed with complete selectivity for endo epoxide opening. This catalytic reaction represents the first use of a non-pi-based electrophile in a growing class of nickel-catalyzed, multicomponent coupling reactions, and is the first catalytic method of reductive coupling of alkynes and epoxides that is effective for both intermolecular and intramolecular cases, and mechanistically distinct from these, possibly involving a nickella(II)oxetane.

  DOI：

  10.1021/ja0361401

文献信息

• Synthesis and Anticancer Activity of 5-(Propargyloxymethyl)-2-oxazolidinones
  作者：R.B. Fugitt、L.C. Martinelli

  DOI：10.1002/jps.2600620637

  日期：1973.6

  determine the feasibility of producing a tissue-specific anticancer agent, a series of 2-oxazolidinones bearing an alkynoxymethyl side chain in the 5-position was prepared. These compounds were submitted to the National Cancer Institute for testing against L-1210 and/or P-388 tumor test systems. None of the compounds showed significant anticancer activity. The synthetic procedures and NMR spectral properties

  摘要：为了确定生产组织特异性抗癌剂的可行性，制备了一系列在5位带有炔氧基甲基侧链的2-恶唑烷酮。这些化合物已提交给美国国家癌症研究所，以针对L-1210和/或P-388肿瘤测试系统进行测试。这些化合物均未显示出显着的抗癌活性。描述了标题化合物的合成方法和NMR光谱性质。
• Nickel-Catalyzed Reductive Coupling of Alkynes and Epoxides
  作者：Carmela Molinaro、Timothy F. Jamison

  DOI：10.1021/ja0361401

  日期：2003.7.1

  Nickel-catalyzed, intramolecular and intermolecular reductive coupling of alkynes and epoxides affords synthetically useful homoallylic alcohols of defined alkene geometry. Very high regioselectivity is generally observed, and cyclizations proceed with complete selectivity for endo epoxide opening. This catalytic reaction represents the first use of a non-pi-based electrophile in a growing class of nickel-catalyzed, multicomponent coupling reactions, and is the first catalytic method of reductive coupling of alkynes and epoxides that is effective for both intermolecular and intramolecular cases, and mechanistically distinct from these, possibly involving a nickella(II)oxetane.