1,2-diphenyl-oct-3-yne-1,2-diol | 104045-12-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2-diphenyl-oct-3-yne-1,2-diol
• 英文别名: 1,2-diphenyloct-3-yne-1,2-diol
• CAS: 104045-12-7
• 化学式: C₂₀H₂₂O₂
• 分子量: 294.393
• InChiKey: YJNVQDZHBBXWAG-UHFFFAOYSA-N

物化性质

• 熔点：
  96 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
• 沸点：
  478.5±45.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  1,2-diphenyl-oct-3-yne-1,2-diol 在 silver(I) nitrate on silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以98%的产率得到5-butyl-2,3-diphenylfuran
  参考文献：
  名称：

  An efficient furan synthesis using heterogeneous catalysis

  摘要：

  A wide variety of 3-alkyne-1,2-diols have been found to undergo exceptionally clean 5-endo-dig cyclisations followed by dehydration at ambient temperature to give the corresponding furans in essentially quantitative yields when exposed to 10 mol % of 10%,w/w silver(1) nitrate absorbed on silica gel. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.08.102
• 作为产物：
  描述：

  安息香精油 、 1-己炔 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 18.0h， 以68%的产率得到1,2-diphenyl-oct-3-yne-1,2-diol
  参考文献：
  名称：

  通过 5-endo-dig 环化快速合成 β-碘呋喃

  摘要：

  使用碘作为亲电子试剂的 3-炔烃-1,2-二醇的 5-endo-dig 环化顺利进行，以提供相应 β-碘呋喃的优异产率。必要的前体可从许多不同的方法中获得，特别是共轭烯炔的区域选择性双羟基化和将乙炔加成到 α-羟基羰基上。最初的碘呋喃可以使用多种策略进行同系化，从各种过渡金属催化偶联到卤素-金属交换以及随后与亲电子试剂的偶联。因此，该方法总体上代表了一种灵活、相对简短且非常有效的方法来处理各种高度取代的呋喃。© Wiley-VCH Verlag GmbH & Co. KGaA，2007 年。

  DOI：

  10.1002/ejoc.200700681

文献信息

• Synthesis of Substituted Furan/Pyrrole-3-carboxamides through a Tandem Nucleopalladation and Isocyanate Insertion
  作者：Manda Rajesh、Surendra Puri、Ruchir Kant、Maddi Sridhar Reddy

  DOI：10.1021/acs.orglett.6b02077

  日期：2016.9.2

  furanyl- and pyrrolyl-3-carboxamides from readily available 3-alkyne-1,2-diols and 1-amino-3-alkyn-2-ols using isocyanate as amido surrogate is demonstrated. The approach constitutes a successful unprecedented combination of heteropalladation and isocyanate insertion, a new avenue for novel amide bond constructions. The mechanism likely involves a 6-membered oxaaminopalladacycle as the key intermediate.

  证明了使用异氰酸酯作为酰胺代用品可以从现成的3-炔基-1,2-二醇和1-氨基-3-炔基-2-醇中获得呋喃基和吡咯基3-羧酰胺。该方法构成了异palpalpalation和异氰酸酯插入成功的前所未有的组合，这是新型酰胺键结构的新途径。该机制可能涉及6元的oxaaminopalladacycle作为关键中间体。
• On the highly stereoselective addition of lithio-acetylides to α-hydroxy-ketones
  作者：Damian Dunford、Mathilde Guyader、Simon Jones、David W. Knight、Michael B. Hursthouse、Simon J. Coles

  DOI：10.1016/j.tetlet.2008.02.032

  日期：2008.3

  Addition of 2 equiv of a lithio-acetylide to an unprotected alpha-hydroxy ketone is extremely stereoselective in examples where the two ketone substituents are relatively large. (C) 2008 Elsevier Ltd. All rights reserved.
• 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.
• WO2006/100479
  申请人：——

  公开号：——

  公开（公告）日：——