3-(naphthalen-1-yl)-1H-isochromen-1-one | 571186-24-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: 3-(naphthalen-1-yl)-1H-isochromen-1-one
• 英文别名: 3-Naphthalen-1-ylisochromen-1-one
• CAS: 571186-24-8
• 化学式: C₁₉H₁₂O₂
• 分子量: 272.303
• InChiKey: MLBULWNZNFKVRF-UHFFFAOYSA-N

物化性质

• 熔点：
  132 °C
• 沸点：
  474.0±45.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• 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：

  3-(naphthalen-1-yl)-1H-isochromen-1-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 以81%的产率得到3-(naphthalen-1-yl)-1H-isochromene-1-thione
  参考文献：
  名称：

  Synthesis and Antiproliferative Activity of Some 1H-Isochromen-1-ones and Their Thio Analogues

  摘要：

  A series of 1H-isochromen-1-one derivatives and their thio analogues were synthesized by thionation using Lawesson's reagent for evaluation of their cytotoxic effect on cancer cells. The effect of these derivatives was tested on the growth of human epidermoid carcinoma A431 cell line by MTT [3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide] colorimetric assay. MTT assay revealed that these new compounds are potent inhibitors of cell growth. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

  DOI：

  10.1080/10426500902797608
• 作为产物：
  描述：

  1-乙炔基萘 在 五羰基氯铼(I) 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 3-(naphthalen-1-yl)-1H-isochromen-1-one
  参考文献：
  名称：

  Synthesis of Isocoumarins: Rhenium Complex-Catalyzed Cyclization of 2-Ethynylbenzoic Acids

  摘要：

  When 2-ethynylbenzoic acids were treated with a catalytic amount of a rhenium complex, such as ReCl(CO())5, 6-endo cyclization of 2-ethynylbenzoic acids proceeded with a high selectivity to give the corresponding isocoumarins in moderate to good yields.

  DOI：

  10.3987/com-15-13311

文献信息

• 3-Substituted Isocoumarins as Thymidine Phosphorylase Inhibitors
  作者：Khalid Mohammed Khan、Sumbul Ahmed、Sajjad Hussain、Nida Ambreen/snm、>、Shahnaz Perveen、M. Iqbal Choudhary

  DOI：10.2174/157018010790945805

  日期：2010.5.1

  3-Substituted isocoumarins 1-19 were synthesized and evaluated for their thymidine phosphorylase inhibitory activity. Eight (8) compounds exhibited a varying degree of inhibitory activity towards thymidine phosphorylase from E. coli with IC50 values between 61- 402 iM. The activities were compared with the standard 7-deazaxanthine (IC50 = 39.28 ± 0.76 iM).

  合成了3-取代异香豆素1-19，并评估了它们对大肠杆菌胸苷磷酸化酶的抑制活性。其中8个化合物表现出不同程度的抑制作用，IC50值介于61至402微摩尔之间。将这些活性与标准物质7-去氮黄嘌呤（IC50 = 39.28 ± 0.76微摩尔）进行比较。
• Sulfoxonium Ylides as Carbene Precursors: Rhodium(III)‐Catalyzed Sequential C−H Functionalization, Selective Enol Oxygen‐Atom Nucleophilic Addition, and Hydrolysis
  作者：Yuanqiong Huang、Xueli Lyu、Hongjian Song、Qingmin Wang

  DOI：10.1002/adsc.201900861

  日期：2019.11.19

  Herein, we report a protocol for Rh(III)‐catalyzed annulation reactions between oxazolines and sulfoxonium ylides via a sequence involving C−H activation, selective enol oxygen‐atom nucleophilic addition, and hydrolysis. This practical, operationally simple protocol has a wide substrate range, excellent regioselectivity, and moderate to good yields.

  在本文中，我们报告了通过Rh活化催化，选择性烯醇氧原子亲核加成和水解的序列，Rh（III）催化的恶唑啉和亚砜基鎓盐之间的环化反应的协议。该实用，操作简单的方案具有广泛的底物范围，出色的区域选择性以及中等至良好的产率。
• Copper-catalyzed annulation of 2-bromobenzoic esters with terminal alkynes towards 3-substituted isocoumarins
  作者：Mengli Sun、Lebin Su、Jianyu Dong、Long Liu、Yongbo Zhou、Shuang-Feng Yin

  DOI：10.1016/j.tetlet.2017.05.019

  日期：2017.6

  An efficient method for the synthesis of 3-substituted isocoumarins that are an important class of biologically active scaffolds via annulation of 2-bromobenzoic esters with terminal alkynes by copper catalyzed is described. The advantages of this method include mild reaction conditions, high yield and regioselectivity, and wide tolerance toward functional groups.

  描述了通过铜催化的2-溴苯甲酸酯与末端炔烃的环合反应来合成作为重要的一类生物活性支架的3-取代的香豆素的有效方法。该方法的优点包括温和的反应条件，高收率和区域选择性以及对官能团的广泛耐受性。
• Fluorination-triggered tandem cyclization of styrene-type carboxylic acids to access 3-aryl isocoumarin derivatives under microwave irradiation
  作者：Jinwei Yuan、Fanlin Zeng、Wenpeng Mai、Liangru Yang、Yongmei Xiao、Pu Mao、Donghui Wei

  DOI：10.1039/c9ob00509a

  日期：——

  A practical synthetic route through a fluorination-triggered tandem cyclization of styrene-type carboxylic acids was developed to construct a variety of 4-fluoro-3-aryl-3,4-dihydroisocoumarins and 3-arylisocoumarins.

  通过氟化触发串联环化反应合成苯乙烯型羧酸的实用合成路线被开发出来，用于构建各种4-氟-3-芳基-3,4-二氢异香豆素和3-芳基异香豆素。
• Diselenide- and Disulfide-Mediated Synthesis of Isocoumarins
  作者：Sohail A. Shahzad、Claire Venin、Thomas Wirth

  DOI：10.1002/ejoc.201000308

  日期：——

  Cyclizations of stilbenecarboxylic acids to the corresponding isocoumarin derivatives using diselenide or disulfide reagents have been developed. By employing bis(triflouroacetoxy)iodobenzene as oxidant for the 6-endo-trig cyclizations a variety of dihydroisocoumarins have been prepared in good yields. This method is capable of forming isocoumarins and dihydroisocoumarin derivatives by a cyclization–elimination

  已经开发出使用二硒化物或二硫化物试剂将芪甲酸环化为相应的异香豆素衍生物。通过使用双（三氟乙酰氧基）碘苯作为 6-endo-trig 环化的氧化剂，已经以良好的收率制备了多种二氢异香豆素。该方法能够通过环化-消除路线形成异香豆素和二氢异香豆素衍生物。