8-(naphthalen-1-yl)-2H-chromen-2-one | 3023-98-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 8-(naphthalen-1-yl)-2H-chromen-2-one
• 英文别名: 2H-naphtho[2,3-b]pyran-2-one；2H-benzo[g]chromen-2-one；6,7-benzocoumarin；benzo[g]chromen-2-one；3c-(3-Hydroxy-[2]naphthyl)-acrylsaeure-lacton；Benzo[g]chromen-2-on；benzo[g]chromen-2-one
• CAS: 3023-98-1
• 化学式: C₁₃H₈O₂
• 分子量: 196.205
• InChiKey: JKOCGAMDKVAHCI-UHFFFAOYSA-N

物化性质

• 熔点：
  163-164 °C
• 沸点：
  402.6±14.0 °C(Predicted)
• 密度：
  1.297±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-(naphthalen-1-yl)-2H-chromen-2-one 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 aluminum nickel 、 对甲苯磺酸 作用下， 以 乙醚 、 苯 为溶剂， 反应 4.0h， 生成 3,4-dihydro-2H-naphtho[2,3-b]pyran
  参考文献：
  名称：

  Ranade, Anup A.; Joseph, Augustine R.; Kumbhar, Virendra B., Journal of Chemical Research, Miniprint, 2003, # 8, p. 857 - 868

  摘要：

  DOI：
• 作为产物：
  描述：

  5,6,7,8-四氢-2-萘酚 在 硫酸 、 过氧化苯甲酰 作用下， 生成 8-(naphthalen-1-yl)-2H-chromen-2-one
  参考文献：
  名称：

  Nakabayashi, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1957, vol. 77, p. 527,530

  摘要：

  DOI：

文献信息

• INTRACELLULAR DELIVERY VEHICLE
  申请人：KIRIN KABUSHIKI KAISHA

  公开号：US20190137503A1

  公开（公告）日：2019-05-09

  An intracellular delivery vehicle of which surface is covered by a positive charge, an intracellular delivery complex in which a component or compound desired is loaded in the intracellular delivery vehicle, a temperature-sensitive probe comprising the intracellular delivery complex, and a method for measuring the intracellular temperature by the temperature-sensitive probe are disclosed. The intracellular delivery vehicle is useful on account of its capability of easily delivering the component or compound desired inside the cell without inhibiting cell proliferation.

  一个表面覆盖正电荷的细胞内传递载体，一个所需成分或化合物装载在细胞内传递载体中的细胞内传递复合物，包括细胞内传递复合物的温度敏感探针，以及通过温度敏感探针测量细胞内温度的方法被揭示。由于其能够轻松将所需成分或化合物传递到细胞内而不抑制细胞增殖，这种细胞内传递载体非常有用。
• Rh-Catalyzed Synthesis of Coumarin Derivatives from Phenolic Acetates and Acrylates <i>via</i> C–H Bond Activation
  作者：Sunita K. Gadakh、Soumen Dey、Arumugam Sudalai

  DOI：10.1021/acs.joc.5b01713

  日期：2015.11.20

  An efficient annulation strategy involving the reaction of phenolic acetates with acrylates in the presence of [Rh2(OAc)4] as catalyst and formic acid as reducing agent, leading to the high yield synthesis of coumarin derivatives, has been developed. The addition of NaOAc as a base increased the yield of the products. The reaction is quite successful for both electron-rich as well as electron-deficient

  已经开发出一种有效的环化策略，该方法涉及在[Rh 2（OAc）4 ]作为催化剂和甲酸作为还原剂的存在下使酚醛乙酸酯与丙烯酸酯反应，从而导致香豆素衍生物的高收率合成。加入NaOAc作为碱提高了产物的产率。该反应是相当成功二者以及缺电子的酚乙酸酯，得到具有优良的区位选择性香豆素，并且进行富电子通过C-H键活化由氘掺入研究证实。
• Ytterbium triflate promoted coupling of phenols and propiolic acids: synthesis of coumarins
  作者：Serena Fiorito、Francesco Epifano、Vito A. Taddeo、Salvatore Genovese

  DOI：10.1016/j.tetlet.2016.05.087

  日期：2016.6

  Coumarins are a well-known class of natural occurring and semi-synthetic products with reported important and effective pharmacological activities. In this Letter an improved method for the chemical synthesis of such compounds is described. Coumarins have been obtained in good to excellent yields under microwave irradiation and solvent-free conditions in a short time from differently substituted phenols

  香豆素是众所周知的天然和半合成产品，具有重要的有效药理活性。在这封信中，描述了一种化学合成这类化合物的改进方法。在10％的Yb（OTf）3水合物作为催化剂存在下，在短时间内从微波辐射和无溶剂条件下，短短地从不同取代的酚和丙酸作为起始原料，以良好的产率获得了香豆素。
• Improvement of Fluorescence Characteristics of Coumarins: Syntheses and Fluorescence Properties of 6-Methoxycoumarin and Benzocoumarin Derivatives as Novel Fluorophores Emitting in the Longer Wavelength Region and Their Application to Analytical Reagents
  作者：Chiyomi Murata、Toshinobu Masuda、Yasuko Kamochi、Kenichiro Todoroki、Hideyuki Yoshida、Hitoshi Nohta、Masatoshi Yamaguchi、Akira Takadate

  DOI：10.1248/cpb.53.750

  日期：——

  To improve the fluorescence characteristics, especially emission wavelength, of coumarins, various 3-substituted-6-methoxycoumarin derivatives were synthesized, and then benzocoumarin derivatives were also synthesized in expectation of the shift to the longer wavelength region by the extension of the conjugated system. Their fluorescence properties were investigated spectrophotometrically in acetonitrile and evaluated from the viewpoint of the intramolecular charge transfer (ICT) between push- and pull-substituents in the ground and the excited states. Among them, benzocoumarin derivatives especially fluoresced in the longer wavelength around 540 nm with remarkably large Stokes shifts beyond 10000 cm−1. Using such fluorophores, some novel fluorescence derivatization reagents for carboxylic acids, alcohols, phenols, and amines were preliminarily prepared as an example, and their derivatized products were also found to fluoresce in the longer wavelength region with large Stokes shifts.

  为了改善香豆素的荧光特性，特别是发射波长，合成了多种3取代-6-甲氧基香豆素衍生物，随后又合成了苯香豆素衍生物，期待通过延长共轭体系实现向长波长区域的转移。采用光谱法在乙腈中研究了它们的荧光特性，并从基态和激发态中推送和拉动取代基之间的分子内电荷转移（ICT）角度进行了评估。在这些衍生物中，苯香豆素衍生物特别在540 nm附近的长波长范围内具有显著的荧光，斯托克斯位移超过10000 cm−1。利用这些荧光基团，初步制备了一些新型的荧光衍生化试剂用于羧酸、醇、酚和胺，发现其衍生化产物在长波长区域也具有显著的荧光和较大的斯托克斯位移。
• Transition Metal-Free Oxidative Cross-Coupling C(<i>sp</i> ² )-C(<i>sp</i> ³ ) Bond Formation: Regioselective C-3 Alkylation of Coumarins with Tertiary Amines
  作者：Longyang Dian、Daisy Zhang-Negrerie、Yunfei Du

  DOI：10.1002/adsc.201700521

  日期：2017.9.18

  A novel transition‐metal‐free regioselective C‐3 alkylation of coumarins was realized under mild reaction conditions. Various coumarins and tertiary amines smoothly underwent direct C(sp2)–C(sp3) bond formation in the presence of (n‐Bu)4NI as the catalyst and t‐BuOOH as the oxidant.

  在温和的反应条件下实现了一种新型的无过渡金属的香豆素区域选择性C-3烷基化反应。在（n- Bu）4 NI作为催化剂和t- BuOOH作为氧化剂的情况下，各种香豆素和叔胺顺利地直接形成C（sp 2）–C（sp 3）键。