2,3-dihydro-3-phenyl-1H-naphtho[2,1-b]pyran | 13255-85-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2,3-dihydro-3-phenyl-1H-naphtho[2,1-b]pyran
• 英文别名: 3,4-dihydro-2-phenyl-2H-benzo[f]chromene；3-phenyl-2,3-dihydro-1H-benzo[f]chromene；3-phenyl-2,3-dihydro-1H-benzo[f]chromene
• CAS: 13255-85-1
• 化学式: C₁₉H₁₆O
• 分子量: 260.335
• InChiKey: ZIBOQYDDUXXWTB-UHFFFAOYSA-N

物化性质

• 熔点：
  86 °C
• 沸点：
  436.4±35.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 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：

  sodium 2-naphtholate 以 苯 为溶剂， 反应 5.0h， 生成 2,3-dihydro-3-phenyl-1H-naphtho[2,1-b]pyran
  参考文献：
  名称：

  Photocyclization of cinnamylnaphthols

  摘要：

  DOI：

  10.1016/s0040-4020(98)00147-1

文献信息

• Trapping of Active Methylene Intermediates with Alkenes, Indoles or Thiols: Towards Highly Selective Multicomponent Reactions
  作者：Yanlong Gu、Joël Barrault、François Jérôme

  DOI：10.1002/adsc.200900593

  日期：2009.12

  In this paper, a basic method to access new multicomponent reactions (MCRs) is reported. The mechanism of these MCRs is based on the trapping of methylene intermediates, formed in situ by reaction of formaldehyde with electron-rich carbons, with alkene, thiol or indole derivatives. According to our strategy, a wide range of valuable skeletons has been obtained in a one-pot reaction, thus allowing a

  在本文中，报告了一种访问新的多组分反应（MCR）的基本方法。这些MCR的机理基于对亚甲基中间体的捕获，该中间体是通过甲醛与富含电子的碳与烯烃，硫醇或吲哚衍生物反应原位形成的。根据我们的策略，通过一锅法反应已经获得了多种有价值的骨架，因此可以最大程度地减少浪费，成本和劳动力。所提出的方法展示了广泛的底物范围，并且发现羟基或羰基的α-位的富电子碳特别有效。更广泛地讲，这项工作为从最简单的有机组成部分之一甲醛创造分子复杂性和多样性提供了新的工具。
• 4,5-Dimethyl-2-Iodoxybenzenesulfonic Acid Catalyzed Site-Selective Oxidation of 2-Substituted Phenols to 1,2-Quinols
  作者：Muhammet Uyanik、Tatsuya Mutsuga、Kazuaki Ishihara

  DOI：10.1002/anie.201612463

  日期：2017.3.27

  dearomatization of 2‐substituted phenols to either 1,2‐benzoquinols or their cyclodimers, catalyzed by 4,5‐dimethyl‐2‐iodoxybenzenesulfonic acid with Oxone, has been developed. Natural products such as biscarvacrol and lacinilene C methyl ether could be synthesized efficiently under mild reaction conditions. Furthermore, both the reaction rate and site selectivity could be further improved by the introduction of

  已开发了由4,5-二甲基-2-碘氧基苯磺酸与Oxone催化的2-取代酚选择性地羟基化脱芳香化为1,2-苯并喹啉或其环二聚体。在温和的反应条件下，可以有效地合成天然产物，例如联萘香酚和乳香油基C甲醚。此外，通过在苯酚的2位引入三烷基甲硅烷基甲基取代基，可以进一步提高反应速度和位点选择性。通过[4 + 2]环加成级联反应可以将相应的1,2-喹诺酚转化为各种有用的结构基序。
• Synthesis of Chromans from the Reaction of O-quinone Methide Precursor with Substituted Styrenes
  作者：Sevim Bilgiç、Orhan Bilgiç、Bülent Büyükkıdan、Murat Gündüz

  DOI：10.3184/030823407x198131

  日期：2007.2

  cycloaddition reaction of 1-dimethylaminomethyl-2-naphthol and 2-dimethylaminomethyl-4,5-dimethylphenol with (un)substituted styrenes were investigated. 3,4-Dihydro 2-(un)substitutedphenyl-2H-benzo[f]chromenes and 2-(un)substitutedphenyl-6,7-dimethylchromans were isolated from the reaction of 1-dimethylaminomethyl-2-naphthol and 2-dimethylaminomethyl-4,5-dimethylphenol with (un)substituted styrenes. The yields

  在这项工作中，研究了 1-二甲基氨基甲基-2-萘酚和 2-二甲基氨基甲基-4,5-二甲基苯酚与（未）取代的苯乙烯的反电子需求 Diels-Alder 环加成反应。3,4-二氢2-(未)取代苯基-2H-苯并[f]色烯和2-(未)取代苯基-6,7-二甲基色满从1-二甲氨基甲基-2-萘酚和2-二甲氨基甲基-的反应中分离出来4,5-二甲基苯酚和（未）取代的苯乙烯。曼尼希碱的产率以及它们与（未）取代的苯乙烯的反应似乎从邻位取代到对位取代增加。
• Molecular iodine catalyst promoted synthesis of chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling
  作者：Mayuri M. Naik、Durga P. Kamat、Santosh G. Tilve、Vijayendra P. Kamat

  DOI：10.1016/j.tet.2014.05.093

  日期：2014.8

  Molecular iodine as an inexpensive catalyst is described in the construction of 2-substituted or 2,2-disubstituted chromans and 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling. For the synthesis of chromans, phenols and allylic alcohols were refluxed in chloroform in presence of 20 mol % I-2 while [3+3] cyclocoupling of phenols and cinnamic acids proceeded to give 4-aryl-3,4-dihydrobenzopyran-2-ones using 30 mol % I-2. Later reaction occurs via a tandem hydroarylation-esterification process at 120-130 degrees C under solvent free conditions. Chromans were obtained in 20-92% yields and substituted 4-aryl-3,4-dihydrobenzopyran-2-ones were obtained in 5-85% yields. (C) 2014 Elsevier Ltd. All rights reserved.