2-hex-1-ynyloct-3-yne-1,2-diol | 1401246-04-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-hex-1-ynyloct-3-yne-1,2-diol
• 英文别名: 2-Hex-1-ynyloct-3-yne-1,2-diol
• CAS: 1401246-04-5
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: XAJZWQWIZOELBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-hex-1-ynyloct-3-yne-1,2-diol 在 copper dichloride 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以87%的产率得到2-butyl-4-hex-1-ynylfuran
  参考文献：
  名称：

  Copper-Catalyzed Synthesis of Substituted Furans and Pyrroles by Heterocyclodehydration and Tandem Heterocyclodehydration–Hydration of 3-Yne-1,2-diols and 1-Amino-3-yn-2-ol Derivatives

  摘要：

  CuCl2-catalyzed heterocyclodehydration of readily available 3-yne-1,2-diols and 1-amino-3-yn-2-ol derivatives afforded substituted furans and pyrroles, respectively, in good to high yields (53-99%) under mild conditions (MeOH as the solvent, 80-100 degrees C, 1-24 h). In the case of 2,2-dialkynyl-1,2-diols, bearing an additional alkynyl substituent at C-2, a cascade process, corresponding to copper-catalyzed heterocyclodehydration followed by acid-catalyzed hydration of the triple bond, was realized when the reaction was carried out in the presence of both CuCl2 and TsOH, leading to 3-acylfurans in one step and high yields (75-84%). Under the same conditions, N-Boc-2-alkynyl-1-amino-3-yn-2-ols were converted into the corresponding N-unsubstituted 3-acylpyrroles in low to fair yields (19-59%). However, working in the presence of added water and a large excess of CO2 (40 atm), in addition to CuCl2 and TsOH, caused a significant improvement of the yields of 3-acylpyrroles (68-87%), thus making the method of general synthetic applicability.

  DOI：

  10.1021/jo400533j
• 作为产物：
  描述：

  羟乙酸甲酯 、 1-己炔 在 正丁基锂 、 lithium bromide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以74%的产率得到2-hex-1-ynyloct-3-yne-1,2-diol
  参考文献：
  名称：

  碘化钯直接催化3-Yne-1,2-二醇衍生物的氧化羰基化反应合成呋喃-3-羧酸和4-亚甲基-4,5-二氢呋喃-3-羧酸酯

  摘要：

  通过PdI 2 / KI一步一步将各种在C-1上带有伯或仲醇基的3-yne-1,2-二醇衍生物1有效地转化为高附加值的呋喃-3-羧酸酯2 -催化的直接氧化羰基化反应，该反应是在酒精介质中，相对温和的条件下进行的（100℃，在40个大气压下，CO和空气的4/1混合物）。通过仅使用氧气作为外部氧化剂，通过连续的5-内挖-杂环-烷氧基羰基化-脱水过程，可以以相当高的分离产率（56-93％）获得羰基化呋喃2。在类似条件下，2-甲基-3-炔-1,2-二醇3带有叔醇基团的化合物，以令人满意的收率（58-70％）提供了4-亚甲基-4,5-二氢呋喃-3-羧酸酯4。

  DOI：

  10.1021/jo301628n

文献信息

• Synthesis of Furan-3-carboxylic and 4-Methylene-4,5-dihydrofuran-3-carboxylic Esters by Direct Palladium Iodide Catalyzed Oxidative Carbonylation of 3-Yne-1,2-diol Derivatives
  作者：Bartolo Gabriele、Raffaella Mancuso、Vito Maltese、Lucia Veltri、Giuseppe Salerno

  DOI：10.1021/jo301628n

  日期：2012.10.5

  A variety of 3-yne-1,2-diol derivatives 1, bearing a primary or secondary alcoholic group at C-1, have been efficiently converted into high value added furan-3-carboxylic esters 2 in one step by PdI2/KI-catalyzed direct oxidative carbonylation, carried out in alcoholic media under relatively mild conditions (100 °C under 40 atm of a 4/1 mixture of CO and air). Carbonylated furans 2 were obtained in

  通过PdI 2 / KI一步一步将各种在C-1上带有伯或仲醇基的3-yne-1,2-二醇衍生物1有效地转化为高附加值的呋喃-3-羧酸酯2 -催化的直接氧化羰基化反应，该反应是在酒精介质中，相对温和的条件下进行的（100℃，在40个大气压下，CO和空气的4/1混合物）。通过仅使用氧气作为外部氧化剂，通过连续的5-内挖-杂环-烷氧基羰基化-脱水过程，可以以相当高的分离产率（56-93％）获得羰基化呋喃2。在类似条件下，2-甲基-3-炔-1,2-二醇3带有叔醇基团的化合物，以令人满意的收率（58-70％）提供了4-亚甲基-4,5-二氢呋喃-3-羧酸酯4。
• Copper-Catalyzed Synthesis of Substituted Furans and Pyrroles by Heterocyclodehydration and Tandem Heterocyclodehydration–Hydration of 3-Yne-1,2-diols and 1-Amino-3-yn-2-ol Derivatives
  作者：Bartolo Gabriele、Lucia Veltri、Pierluigi Plastina、Raffaella Mancuso、Mabel V. Vetere、Vito Maltese

  DOI：10.1021/jo400533j

  日期：2013.5.17

  CuCl2-catalyzed heterocyclodehydration of readily available 3-yne-1,2-diols and 1-amino-3-yn-2-ol derivatives afforded substituted furans and pyrroles, respectively, in good to high yields (53-99%) under mild conditions (MeOH as the solvent, 80-100 degrees C, 1-24 h). In the case of 2,2-dialkynyl-1,2-diols, bearing an additional alkynyl substituent at C-2, a cascade process, corresponding to copper-catalyzed heterocyclodehydration followed by acid-catalyzed hydration of the triple bond, was realized when the reaction was carried out in the presence of both CuCl2 and TsOH, leading to 3-acylfurans in one step and high yields (75-84%). Under the same conditions, N-Boc-2-alkynyl-1-amino-3-yn-2-ols were converted into the corresponding N-unsubstituted 3-acylpyrroles in low to fair yields (19-59%). However, working in the presence of added water and a large excess of CO2 (40 atm), in addition to CuCl2 and TsOH, caused a significant improvement of the yields of 3-acylpyrroles (68-87%), thus making the method of general synthetic applicability.