2,2,5,7-tetramethyl-2H-chromene | 205927-07-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2,2,5,7-tetramethyl-2H-chromene
• 英文别名: 2,2,5,7-Tetramethyl-2H-1-benzopyran；2,2,5,7-tetramethylchromene
• CAS: 205927-07-7
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: XZTNHYHSTPXJMV-UHFFFAOYSA-N

物化性质

• 沸点：
  276.5±40.0 °C(Predicted)
• 密度：
  0.982±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-(1,1-Dimethyl-prop-2-ynyloxy)-3,5-dimethyl-benzene 在 氯化铂 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以90%的产率得到2,2,5,7-tetramethyl-2H-chromene
  参考文献：
  名称：

  Pt(IV)-catalyzed cyclization of arene–alkyne substrates via C–H bond functionalization

  摘要：

  We herein report that PtCl4 has proven to be a hydroarylation catalyst with an efficiency and substrate scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-yne substrates of diverse structural features, including propargyl ethers, propargylamines, and alkynoate esters, providing good to excellent yields of the 6-endo products (chromenes, dihydroquinolines, and coumarins). In contrast, Pt(II), Pd(II), and Ga(III) salts were shown to be sensitive to the substitution on the alkyne moiety. PtCl4 is compatible with both terminal and disubstituted alkynes, as well as with various functionalities on the arene ring, including methyl, methoxyl, hydroxyl, protected amine, and halide. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.05.003

文献信息

• USE OF COMPOSITIONS OBTAINED BY CALCINING PARTICULAR METAL-ACCUMULATING PLANTS FOR IMPLEMENTING CATALYTICAL REACTIONS
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE

  公开号：US20150376224A1

  公开（公告）日：2015-12-31

  The use of metal-accumulating plants for implementing chemical reactions especially catalytical reactions.

  金属积累植物用于实现化学反应，特别是催化反应的使用。
• An efficient and simple method for synthesis of 2,2-disubstituted-2H-chromenes by condensation of a phenol with a 1,1-disubstituted propargyl alcohol using BF3·Et2O as the catalyst
  作者：Sridhar Madabhushi、Raveendra Jillella、Kondal Reddy Godala、Kishore Kumar Reddy Mallu、China Ramanaiah Beeram、Narsaiah Chinthala

  DOI：10.1016/j.tetlet.2012.07.077

  日期：2012.9

  An efficient and simple method for the synthesis of 2,2-disubstituted-2H-chromenes by one-step cyclocondensation of a phenol with a variety of 1,1-disubstituted propargyl alcohols using BF3·Et2O as the catalyst is described.

  描述了一种以BF 3 ·Et 2 O为催化剂，通过苯酚与多种1,1-二取代的炔丙基醇的一步式环缩合反应合成2,2-二取代的2 H-色烯的有效而简单的方法。
• Boronic acid/Brønsted acid co-catalyst systems for the synthesis of 2H-chromenes from phenols and α,β-unsaturated carbonyls
  作者：Victoria Dimakos、Tishaan Singh、Mark S. Taylor

  DOI：10.1039/c6ob01026a

  日期：——

  Protocols for the synthesis of substituted 2H-chromenes from α,β-unsaturated carbonyls and phenols are described. Optimal combinations of arylboronic acids and Brønsted acids have been identified, such that both can be employed in catalytic quantities to accelerate these condensations. The method has been used to synthesize a variety of substituted 2H-chromenes, as well as photochromic naphthopyrans

  描述了由α，β-不饱和羰基和苯酚合成取代的2 H-色烯的方案。已经确定了芳基硼酸和布朗斯台德酸的最佳组合，因此可以催化量同时使用两者来加速这些缩合反应。该方法已用于合成各种取代的2 H-苯甲基以及光致变色萘并吡喃。五氟苯基硼酸和二苯基次膦酸的使用使得亲电子试剂的范围扩大到包括α，β-不饱和酮。霍尔的硼酸“相变”已被开发出来，可以通过简单的液-液萃取将两种助催化剂从未纯化的反应混合物中分离出来。
• Pd-Catalyzed Formal [3 + 3] Heteroannulation of Allylic <i>gem</i>-Diacetates: Synthesis of Chromene-Based Natural Products and Exploration of Photochromic Properties
  作者：Prashant Kumar、Pravesh Kumar、Sugumar Venkataramani、S. S. V. Ramasastry

  DOI：10.1021/acscatal.1c05450

  日期：2022.1.21

  meta-substituted phenols) to produce novel polycyclic chromenes possessing spiro-, tri-, and tetrasubstituted carbon centers. The versatility of the method is demonstrated in the synthesis of several chromene-based bioactive natural products. Further, interesting photochromic properties of the new classes of benzo[f]chromenes are also discovered.

  很少探索钯催化的烯丙基偕二乙酸酯的烯丙基烷基化反应。这项工作揭示了烯丙基宝石-二乙酸酯的一种不寻常的化学反应模式，并将它们确立为合成复杂苯并[ f ]色烯系统的新原型。在反应条件下，二乙酸酯表现为 1,3-双阳离子等价物，并与 2-萘酚（和间位取代的酚）发生 [3 + 3] 杂环化反应，生成具有螺、三和四取代碳的新型多环色烯中心。该方法的多功能性在几种基于色烯的生物活性天然产物的合成中得到证明。此外，新类别苯并[ f]铬烯也被发现。
• A simple two steps ytterbium triflate-catalysed preparation of 2,2-dimethyl-2<i>h</i>-chromenes from salicylaldehydes and 2-methylpropene
  作者：Soizic Prado、Yves L. Janin、Pierre-Etienne Bost

  DOI：10.1002/jhet.5570430626

  日期：2006.11

  The preparation of various 2,2-dimethyl-2H-chromenes was achieved in two steps via an ytterbium triflate-catalysed reaction between salicylaldehydes, trimethylorthoformate and 2-methylpropene. From salicylaldehyde, two reaction products were characterised: 4-methoxy-2,2-dimethylchroman and 2-(1,3-dimethoxy-3-methylbutyl)phenol. The former compound probably results from a Lewis acid-catalysed [2+4]

  通过水杨醛醛，原甲酸三甲酯和2-甲基丙烯之间的三氟乙磺酸y催化的反应，可分两步完成各种2,2-二甲基-2 H-色烯的制备。由水杨醛表征两个反应产物：4-甲氧基-2，2-二甲基苯并吡喃和2-（1，3-二甲氧基-3-甲基丁基）苯酚。前一种化合物可能是由路易斯酸催化的中间体醌甲基化物和2-甲基丙烯之间的[2 + 4]环加成反应产生的，而后者可能是通过与醌甲基化物和2-甲基丙烯之间的羰基烯反应有关的反应而发生的。两种化合物都经过催化酸性处理，生成2,2-二甲基-2 H-chromene。从各种水杨醛开始，研究了该方法的范围。