1,2,4-三苯基-丁-3-炔-1,2-二醇 | 102705-79-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 中文名称: 1,2,4-三苯基-丁-3-炔-1,2-二醇
• 英文名称: 1,2,4-triphenylbut-3-yne-1,2-diol
• 英文别名: 1,2,4-Triphenylbut-3-yne-1,2-diol
• CAS: 102705-79-3
• 化学式: C₂₂H₁₈O₂
• 分子量: 314.384
• InChiKey: PWSFEASFEOWDMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  1,2,4-三苯基-丁-3-炔-1,2-二醇 在 gold(III) bromide 、 碘 、 silver trifluoromethanesulfonate 作用下， 以 水 为溶剂， 反应 2.0h， 以93%的产率得到3-iodo-2,4,5-triphenylfuran
  参考文献：
  名称：

  利用胶束效应：室温下金催化的水中脱水环化

  摘要：

  介绍了在水介质中金催化的二醇和三醇环化成相应杂环或螺环的第一个例子。这些反应发生在纳米胶束内，疏水作用在其中起作用，从而推动脱水，尽管周围有水。通过添加简单的盐，例如氯化钠，可以显着减少反应时间和催化剂负载。

  DOI：

  10.1021/ol403402h
• 作为产物：
  描述：

  magnesium,ethynylbenzene,bromide 、 安息香精油 在 乙醚 作用下， 生成 1,2,4-三苯基-丁-3-炔-1,2-二醇
  参考文献：
  名称：

  Salkind; Martinsson, Zhurnal Obshchei Khimii, 1936, vol. 6, p. 1085,1087

  摘要：

  DOI：

文献信息

• Sustainable Micellar Gold Catalysis - Poly(2-oxazolines) as Versatile Amphiphiles
  作者：Linda Lempke、Andrea Ernst、Fabian Kahl、Ralf Weberskirch、Norbert Krause

  DOI：10.1002/adsc.201600139

  日期：2016.4.28

  the gold‐catalyzed allene cycloisomerizations under aqueous micellar conditions is described. The polymers were prepared by ring‐opening cationic polymerization based on poly(2‐methyl‐2‐oxazoline) as hydrophilic segment and different hydrocarbon‐ or fluorocarbon‐based hydrophobic segments. The catalytic activity in the gold‐catalyzed allene cyclization is strongly dependent on the type of gold precursor

  描述了五种聚合物两亲物在水性胶束条件下在金催化的丙二烯环异构化中的应用。这些聚合物是通过以聚（2-甲基-2-恶唑啉）为亲水链段和不同的基于烃或碳氟化合物的疏水链段通过阳离子聚合开环阳离子而制备的。金催化的异戊烯环化反应中的催化活性在很大程度上取决于金前驱体的类型，本体水介质中的盐浓度以及聚合两亲物的浓度。用2 mol％的溴化金（III），1 mM的两亲物和5 M的氯化钠可获得最佳结果，不同杂环产品的收率超过80％。该催化剂体系也适用于炔二醇的脱水环化成呋喃。而且，
• 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。
• Access to Polysubstituted Furan Derivatives via Cascade Oxy-palladation and Hydrocarbofunctionalization of Unactivated Alkenes
  作者：Shivam Pandey、Rahul K. Shukla、Chandra M. R. Volla

  DOI：10.1021/acs.orglett.3c01571

  日期：2023.6.30

  the synthesis of biologically relevant multisubstituted furans is a much-desired yet challenging task. Herein, we report an efficient and versatile strategy involving two different pathways for the construction of diverse polysubstituted C3- and C2-substituted γ-furanyl carboxylic acid derivatives. The synthetic approach for C3-substituted furans involves intramolecular cascade oxy-palladation of alkyne-diols

  开发合成生物学相关的多取代呋喃的简便策略是一项非常理想但具有挑战性的任务。在此，我们报告了一种有效且通用的策略，涉及两种不同的途径来构建不同的多取代C3-和C2-取代的γ-呋喃基羧酸衍生物。C3 取代呋喃的合成方法涉及炔二醇的分子内级联氧钯化，然后是未活化烯烃的区域选择性配位插入。相比之下，C2 取代的呋喃仅通过以串联方式执行该方案来获得。
• Catalytic and highly enantioselective Friedel–Crafts type reactions of heteroaromatic compounds with trifluoropyruvate and glyoxylate by a dicationic palladium complex
  作者：Kohsuke Aikawa、Yuya Asai、Yūta Hioki、Koichi Mikami

  DOI：10.1016/j.tetasy.2014.06.013

  日期：2014.8

  The highly enantioselective Friedel-Crafts alkylation of furan and thiophene derivatives with trifluoropyruvate, which have never provided the high level of asymmetric induction and yield until now, was achieved by using dicationic palladium complexes as Lewis acid catalysts. Moreover, glyoxylate instead of trifluoropyruvate as an electrophile led to complete change of regioselectivity with 2-trimethylsilylated furan, thiophene, and pyrrole derivatives to give the corresponding heteroarylated products in high yields and enantioselectivities. The respective products with trifluoropyruvate and glyoxylate could also be obtained via sequential catalytic reaction; intramolecular cyclization of alkynyldiols using cationic Au catalyst followed by Friedel-Crafts type reactions using dicationic Pd catalyst. (C) 2014 Elsevier Ltd. All rights reserved.
• An efficient furan synthesis using heterogeneous catalysis
  作者：Simon J. Hayes、David W. Knight、Melanie D. Menzies、Mark O’Halloran、Wen-Fei Tan

  DOI：10.1016/j.tetlet.2007.08.102

  日期：2007.10

  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.