6-羟基-4-苯基-3,4-二氢色烯-2-酮 | 57322-71-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 中文名称: 6-羟基-4-苯基-3,4-二氢色烯-2-酮
• 英文名称: 3,4-dihydro-6-hydroxy-4-phenyl-2H-1-benzopyran-2-one
• 英文别名: 6-hydroxy-4-phenyl-3,4-dihydrobenzopyran-2-one；(+/-)-6-hydroxy-4-phenyl-3,4-dihydrocoumarin；6-hydroxy-3,4-dihydro-4-phenylcoumarin；6-hydroxy-4-phenyldihydrocoumarin；6-hydroxy-4-phenyl-chroman-2-one；6-Hydroxy-4-phenyl-chroman-2-on；6-Hydroxy-4-phenyl-3,4-dihydrochromen-2-one
• CAS: 57322-71-1
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: CTYPLGFAIKYKIV-UHFFFAOYSA-N

物化性质

• 熔点：
  132-133 °C(Solv: ethanol (64-17-5))
• 沸点：
  395.4±41.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-羟基-4-苯基-3,4-二氢色烯-2-酮 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 12.0h， 以86%的产率得到(+/-)-6-acetoxy-4-phenyl-3,4-dihydrocoumarin
  参考文献：
  名称：

  Synthetic and novel biocatalytic resolution studies on (±)-5/6/7-acetoxy-4-aryl-3,4-dihydrocoumarins

  摘要：

  Eleven (+/-)-5/6/7-acetoxy-4-aryl-3,4-dihydrocoumarins have been synthesised in two steps starting from the coupling of cinnamic acid/substituted cinnamic acid with appropriate phenols, followed by acetylation in 50-83% overall yields. All hydroxy- and acetoxycoumarins were unambiguously identified on the basis of their spectral data. Candida antarctica lipase-catalysed deacetylation of these racemic acetoxydihydrocoumarins in dioxane occurred with moderate enantioselectivity. This is one of the rare examples of resolution using phenolic ester moiety as a remote handle for chiral recognition by a lipase. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00454-6
• 作为产物：
  描述：

  肉桂酸 在 对苯二酚 作用下， 以97%的产率得到6-羟基-4-苯基-3,4-二氢色烯-2-酮
  参考文献：
  名称：

  3,3-diphenylpropylamines and pharmaceutical compositions thereof

  摘要：

  式（I）的新型3,3-二苯基丙胺化合物，其中R.sup.1表示氢或甲基，R.sup.2、R.sup.3和R.sup.4独立表示氢、甲基、甲氧基、羟基、氨基甲酰基、磺酰基或卤素，X代表三级氨基-NR.sup.5，R.sup.6，其中R.sup.5和R.sup.6表示非芳香烃基，可以相同也可以不同，并且总共含有至少三个碳原子，它们可以与胺氮形成环，它们与生理上可接受的酸盐，当化合物可以是光学异构体时，它们的消旋混合物和单体对映体，它们作为药物的用途，特别是作为抗胆碱能药物的用途，它们用于制备抗胆碱能药物，含有新型胺的药物制剂，以及其制备方法。

  公开号：

  US05382600A1

文献信息

• Selective Synthesis of 3,4-Dihydrocoumarins and Chalcones from Substituted Aryl Cinnamic Esters
  作者：Jae-Ho Jeon、Deok-Mo Yang、Jong-Gab Jun

  DOI：10.5012/bkcs.2011.32.1.65

  日期：2011.1.20

  Coumarins are ubiquitous in plant kingdom and have been used as antitumor, antifungals, anticoagulants, insecticides. Chalcones are also widespread in plant kingdom and have been known to possess diverse biological activities; antibacterial, antifungal, antitumor and anti-inflammatory, etc. As they are considered as important natural products, numerous synthetic approaches have been reported up to the present. We devise a new selective method of preparing dihydrocoumarins and chalcones from aryl cinnamates by the selection of reagents. Dihydrocoumarin derivatives were prepared selectively by using intramolecular cyclization catalyzed by p-toluene sulfonic acid. Also, chalcones were prepared by Fries-rearrangement catalyzed by $TiCl_4$. This method can be used for preparing various coumarin & chalcone compounds.

  香豆素广泛存在于植物王国中，并已被用作抗癌剂、抗真菌剂、抗凝血剂和杀虫剂。查尔酮也在植物王国中广泛分布，并且已知具有多种生物活性，包括抗菌、抗真菌、抗癌和抗炎等。由于它们被认为是重要的天然产物，迄今为止已经报道了许多合成方法。我们设计了一种新的选择性方法，通过选择试剂，从芳基肉桂酸制备二氢香豆素和查尔酮。通过使用对甲苯磺酸催化的分子内环化反应，选择性地制备了二氢香豆素衍生物。此外，还通过三氯化钛催化的Fries重排反应制备了查尔酮。这种方法可以用于制备各种香豆素和查尔酮化合物。
• Solvent-free synthesis of 4-aryl-3,4-dihydrobenzopyran-2-ones via [3+3] cyclocoupling of phenols with cinnamic acid catalyzed by molecular iodine
  作者：Durga P. Kamat、Santosh G. Tilve、Vijayendra P. Kamat

  DOI：10.1016/j.tetlet.2012.06.069

  日期：2012.8

  Molecular iodine was used as a catalyst in the [3+3] cyclocoupling of phenols and cinnamic acids which proceeds via a tandem esterification–hydroarylation process at 120–130 °C under solvent-free conditions. Substituted 4-aryl-3,4-dihydrobenzopyran-2-ones were obtained in good yields.

  分子碘被用作苯酚和肉桂酸的[3 + 3]环偶联反应的催化剂，该过程在无溶剂条件下通过串联酯化-氢芳基化过程在120-130°C下进行。以高收率获得了取代的4-芳基-3,4-二氢苯并吡喃-2-酮。
• New amines, their use and preparation
  申请人：Kabi Pharmacia AB

  公开号：EP0325571B1

  公开（公告）日：1991-08-07
• Starkov, S. P., Journal of general chemistry of the USSR, 1983, vol. 53, # 9, p. 1892 - 1898
  作者：Starkov, S. P.

  DOI：——

  日期：——
• 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.