6-(benzo[d][1,3]dioxol-5-yl)naphthalen-2-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-(benzo[d][1,3]dioxol-5-yl)naphthalen-2-ol
• 英文别名: 6-(1,3-Benzodioxol-5-yl)naphthalen-2-ol；6-(1,3-benzodioxol-5-yl)naphthalen-2-ol
• 化学式: C₁₇H₁₂O₃
• 分子量: 264.28
• InChiKey: MHUKROXTSMKUSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(benzo[d][1,3]dioxol-5-yl)naphthalen-2-ol 在 N-碘代丁二酰亚胺 、 copper(l) iodide 、 四(三苯基膦)钯 、 对甲苯磺酸 、 二异丙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 2.5h， 生成 6-(benzo[d][1,3]dioxol-5-yl)-1-(3,3-dimethylbut-1-yn-1-yl)naphthalen-2-ol
  参考文献：
  名称：

  炔烃的不对称氢化膦酰化：容易获得轴向手性苯乙烯-膦

  摘要：

  通过新开发的 Cu/CPA 助催化系统，实现了炔烃与亲核氧化膦的直接氢化膦酰化，以高产率和优异的对映选择性（高达 99% 产率和 99% ee）获得新型轴向手性含磷烯烃。进行 DFT 计算以阐明反应途径和对映体控制模型。

  DOI：

  10.1002/anie.202215820
• 作为产物：
  描述：

  6-溴-2-萘酚 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium fluoride 、 potassium acetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 6.0h， 生成 6-(benzo[d][1,3]dioxol-5-yl)naphthalen-2-ol
  参考文献：
  名称：

  Design and synthesis of 2-phenylnaphthalenoids and 2-phenylbenzofuranoids as DNA topoisomerase inhibitors and antitumor agents

  摘要：

  Eight 2-phenylnaphthalenoids (2PNs) (3a h) and twenty four 2-phenylbenzofuranoids (2PBF5) (4a-4j, 5a-5j, 6a, 6f-6h) were successfully designed, synthesized and their antiproliferative and in vitro DNA topoisomerase inhibitory activities were evaluated. Nine compounds (four 2PNs and five 2PBFs) showed either Topol or TopoII alpha inhibitory activities. Six compounds (four 2PNs and two 2PBFs) exhibited potent cytotoxicity with IC50 values for 72 h exposure ranging from 0.3 to above 20 mu M against MDA-MB-231, MDA-MB-435, HepG2 and PC3 cell lines. The two 2PBFs displayed comparable and even better antiproliferative as well as TopoII alpha inhibitory activities than 2PNs. Interestingly, the active 2PBFs displayed different mechanisms of TopoII alpha inhibition from that of 2PNs, suggesting that the chromophore scaffold replacement may result in a change of the binding site of inhibitors to TopoII alpha. Furthermore, the mechanisms of antiproliferation on MDA-MB-231 cells indicate that compounds 5a and 5f are promising for further development of anticancer agents. The results of this study reveal that the evolutionary strategy of medicinal chemistry through scaffold hopping is a promising strategy for structure optimization of TopoII alpha inhibitors. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.07.048

文献信息

• Chiral cobalt(<scp>ii</scp>) complex catalyzed Friedel–Crafts aromatization for the synthesis of axially chiral biaryldiols
  作者：Chaoran Xu、Haifeng Zheng、Bowen Hu、Xiaohua Liu、Lili Lin、Xiaoming Feng

  DOI：10.1039/c7cc05266a

  日期：——

  axially chiral biaryldiols via asymmetric Friedel–Crafts aromatization between p-quinones and 2-naphthols was developed. A chiral cobalt(II) complex of N,N′-dioxide enabled the process to generate axially chiral biaryldiols in up to 98% yield and 95% ee. A large range of substituents at different positions of p-quinones and 2-naphthols was tolerable. The configuration of the product and the chiral N,N′-dioxide-Co(ClO4)2

  通过对苯二酚和2-萘酚之间的不对称Friedel-Crafts芳构化，有效地合成了轴向手性联芳二醇。N，N'-二氧化物的手性钴（II）配合物使该方法能够以高达98％的收率和95％的ee生成轴向手性联芳基二醇。在对苯醌和2-萘酚的不同位置处的大范围的取代基是可容忍的。通过X射线晶体衍射分析确定了产物和手性N，N'-二氧化物-Co（ClO 4）2催化剂的构型，并提出了可能的催化模型。
• Enantioselective Friedel–Crafts Reaction of 2-Alkynyphenols with Aromatic Ethers by Chiral Brønsted Acid Catalysis
  作者：Wenxuan Zhang、Jiaying Sun、Zhendong Lian、Ran Song、Daoshan Yang、Jian Lv

  DOI：10.1021/acs.joc.2c00762

  日期：2022.7.15

  Herein, we report chiral strong Brønsted acid-catalyzed enantioselective Friedel–Crafts reaction of 2-alkynyphenols with aromatic ethers. The reaction affords the corresponding axially chiral styrenes in up to 91% yield and 97% ee.

  在此，我们报道了 2-炔基酚与芳香醚的手性强 Brønsted 酸催化的对映选择性傅克反应。该反应以高达 91% 的收率和 97% ee 提供相应的轴向手性苯乙烯。
• Asymmetric Hydrophosphinylation of Alkynes: Facile Access to Axially Chiral Styrene‐Phosphines
  作者：Baohua Cai、Yuan Cui、Jian Zhou、Yong‐Bin Wang、Limin Yang、Bin Tan、Jun (Joelle) Wang

  DOI：10.1002/anie.202215820

  日期：2023.1.16

  Through a newly developed Cu/CPA co-catalytic system, the direct hydrophosphinylation of alkynes with nucleophilic phosphine oxides was achieved to access novel axially chiral phosphorus-containing alkenes in high yields and excellent enantioselectivities (up to 99 % yield and 99 % ee). DFT calculations were performed to elucidate the reaction pathway and the enantiocontrol model.

  通过新开发的 Cu/CPA 助催化系统，实现了炔烃与亲核氧化膦的直接氢化膦酰化，以高产率和优异的对映选择性（高达 99% 产率和 99% ee）获得新型轴向手性含磷烯烃。进行 DFT 计算以阐明反应途径和对映体控制模型。
• 10.1002/adsc.202400251
  作者：Zhang, Wenxuan、Sun, Jiaying、Yang, Daoshan、Song, Ran、Si, Wen、Lv, Jian

  DOI：10.1002/adsc.202400251

  日期：——

  Herein, we report a chiral Brønsted acid‐catalyzed enantioselective Friedel‐Crafts reaction of ortho‐alkynylnaphthols with various naphthofurans, realizing the asymmetric synthesis of axially chiral styrenes with naphthofurans in 67 to 93% yield and with 34 to 96% ee.

  在此，我们报道了邻炔基萘酚与各种萘并呋喃的手性布朗斯台德酸催化对映选择性弗里德尔-克来福特反应，实现了轴向手性苯乙烯与萘并呋喃的不对称合成，产率为 67% 至 93%，ee 为 34% 至 96%。
• Design and synthesis of 2-phenylnaphthalenoids and 2-phenylbenzofuranoids as DNA topoisomerase inhibitors and antitumor agents
  作者：Huilin Hao、Wang Chen、Jing Zhu、Chunhua Lu、Yuemao Shen

  DOI：10.1016/j.ejmech.2015.07.048

  日期：2015.9

  Eight 2-phenylnaphthalenoids (2PNs) (3a h) and twenty four 2-phenylbenzofuranoids (2PBF5) (4a-4j, 5a-5j, 6a, 6f-6h) were successfully designed, synthesized and their antiproliferative and in vitro DNA topoisomerase inhibitory activities were evaluated. Nine compounds (four 2PNs and five 2PBFs) showed either Topol or TopoII alpha inhibitory activities. Six compounds (four 2PNs and two 2PBFs) exhibited potent cytotoxicity with IC50 values for 72 h exposure ranging from 0.3 to above 20 mu M against MDA-MB-231, MDA-MB-435, HepG2 and PC3 cell lines. The two 2PBFs displayed comparable and even better antiproliferative as well as TopoII alpha inhibitory activities than 2PNs. Interestingly, the active 2PBFs displayed different mechanisms of TopoII alpha inhibition from that of 2PNs, suggesting that the chromophore scaffold replacement may result in a change of the binding site of inhibitors to TopoII alpha. Furthermore, the mechanisms of antiproliferation on MDA-MB-231 cells indicate that compounds 5a and 5f are promising for further development of anticancer agents. The results of this study reveal that the evolutionary strategy of medicinal chemistry through scaffold hopping is a promising strategy for structure optimization of TopoII alpha inhibitors. (C) 2015 Elsevier Masson SAS. All rights reserved.