(S)-5-phenyl-3-(2-phenylethynyl)pent-4-yne-2,3-diol | 1431620-35-7

• 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: (S)-5-phenyl-3-(2-phenylethynyl)pent-4-yne-2,3-diol
• 英文别名: (2S)-5-phenyl-3-phenylethynyl-pent-4-yne-2,3-diol；(S)-5-phenyl-3-(phenylethynyl)pent-4-yne-2,3-diol
• CAS: 1431620-35-7
• 化学式: C₁₉H₁₆O₂
• 分子量: 276.335
• InChiKey: LOPXKSREZDGBIY-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-5-phenyl-3-(2-phenylethynyl)pent-4-yne-2,3-diol 在 SiO₂-supported NaIO₄ 作用下， 以 醋酸异丙酯 为溶剂， 以95%的产率得到1,5-diphenyl-penta-1,4-diyn-3-one
  参考文献：
  名称：

  乳酸乙酯作为合成二炔酮的可再生羰基来源

  摘要：

  乳酸乙酯是一种可持续的原料，是合成高附加值化学品（如跳过的二酮）以及在金催化的转座后结合的二酮的极具吸引力的基础。绿色溶剂参与所有步骤，最终双炔酮的收率很高，在某些情况下，无需任何纯化即可以纯净形式分离出最终的二炔酮。

  DOI：

  10.1039/c8gc03275k
• 作为产物：
  描述：

  L(-)-乳酸乙酯 、 苯乙炔 在 正丁基锂 作用下， 以 2-甲基四氢呋喃 、 正己烷 为溶剂， 反应 3.5h， 以84%的产率得到(S)-5-phenyl-3-(2-phenylethynyl)pent-4-yne-2,3-diol
  参考文献：
  名称：

  乳酸乙酯作为合成二炔酮的可再生羰基来源

  摘要：

  乳酸乙酯是一种可持续的原料，是合成高附加值化学品（如跳过的二酮）以及在金催化的转座后结合的二酮的极具吸引力的基础。绿色溶剂参与所有步骤，最终双炔酮的收率很高，在某些情况下，无需任何纯化即可以纯净形式分离出最终的二炔酮。

  DOI：

  10.1039/c8gc03275k

文献信息

• Regiodivergent Hydration–Cyclization of Diynones under Gold Catalysis
  作者：Marta Solas、Miguel A. Muñoz、Samuel Suárez-Pantiga、Roberto Sanz

  DOI：10.1021/acs.orglett.0c02892

  日期：2020.10.2

  Skipped diynones, efficiently prepared from biomass-derived ethyl lactate, undergo a tandem hydration–oxacyclization reaction under gold(I) catalysis. Reaction conditions have been developed for a switchable process that allows selective access to 4-pyrones or 3(2H)-furanones from the same starting diynones. Further application of this methodology in the total synthesis of polyporapyranone B was demonstrated

  由生物质衍生的乳酸乙酯有效制备的已跳过的二炔酮，在金（I）催化下经历了串联水合-氧环化反应。已经开发了用于可切换过程的反应条件，该过程允许从相同的起始二炔酮选择性地获得4-吡喃酮或3（2 H）-呋喃酮。证明了该方法在聚吡喃酮B的全合成中的进一步应用。
• Poly(ethylene glycol) as a Reaction Matrix in Platinum- or Gold-Catalyzed Cycloisomerization: A Mechanistic Investigation
  作者：Rosella Spina、Evelina Colacino、Jean Martinez、Frédéric Lamaty

  DOI：10.1002/chem.201203800

  日期：2013.3.18

  Design for diversity: A new catalytic system based on PEG‐3400 and a metal salt (Pt or Au) was designed to efficiently perform a cycloisomerization reaction under microwave irradiation, which gave diverse heterocycles in good to excellent yields, after a precipitation/filtration procedure (see scheme).

  多样性设计：设计了一种基于PEG-3400和金属盐（Pt或Au）的新型催化体系，可以在微波辐射下有效地进行环异构化反应，经过沉淀/过滤后，该杂环化合物可以以优良的产率获得优异的多样化杂环（请参阅方案）。
• 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.