2-hydroxy-6-phenylnaphthalene-1-carbaldehyde | 1597710-20-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-6-phenylnaphthalene-1-carbaldehyde
• 英文别名: 2-hydroxy-6-phenyl-1-naphthaldehyde；2-Hydroxy-6-phenylnaphthalene-1-carbaldehyde
• CAS: 1597710-20-7
• 化学式: C₁₇H₁₂O₂
• 分子量: 248.281
• InChiKey: DWTTWICDINPYMD-UHFFFAOYSA-N

物化性质

• 沸点：
  426.4±30.0 °C(predicted)
• 密度：
  1.248±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-hydroxy-6-phenylnaphthalene-1-carbaldehyde 在 哌啶 、 lithium aluminium tetrahydride 、 2-(diphenyl((trimethylsilyl)oxy)methyl)pyrrolidine 、 2,3,4,5,6-五氟苯甲酸 、 Cp*Ir{(S,S)-Pfbsdpen} 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 、 甲苯 为溶剂， 反应 74.33h， 生成
  参考文献：
  名称：

  借氢和动力学动力学拆分联芳基化合物的对映体选择性氧化还原中性胺化反应

  摘要：

  我们在此报告了一种新颖的对芳基化合物的新型对苯二酚选择性氧化还原中性胺化反应，该反应是由手性铱配合物和非手性布朗斯台德酸的协同催化下的借入氢和动态动力学拆分级联触发的。该方案具有广泛的底物范围和良好的官能团耐受性，并允许以高至高收率和高至优异的对映选择性快速组装轴向手性联芳基化合物。

  DOI：

  10.1002/anie.201711126
• 作为产物：
  描述：

  6-溴-2-萘酚 在 potassium phosphate 、 四氯化钛 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 三环己基膦 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 6.25h， 生成 2-hydroxy-6-phenylnaphthalene-1-carbaldehyde
  参考文献：
  名称：

  Development of Pyrazolone and Isoxazol-5-one Cambinol Analogues as Sirtuin Inhibitors

  摘要：

  Sirtuins are a family of NAD+-dependent protein deacetylases that play critical roles in epigenetic regulation, stress responses, and cellular aging in eukaryotic cells. In an effort to identify small molecule inhibitors of sirtuins for potential use as chemotherapeutics as well as tools to modulate sirtuin activity, we previously identified a nonselective sirtuin inhibitor called cambinol (IC50 approximate to 50 mu M for SIRT1 and SIRT2) with in vitro and in vivo antilymphoma activity. In the current study, we used saturation transfer difference (STD) NMR experiments with recombinant SIRT1 and 20 to map parts of the inhibitor that interacted with the protein. Our ongoing efforts to optimize cambinol analogues for potency and selectivity have resulted in the identification of isoform selective analogues: 17 with >7.8-fold selectivity for SIRT1, 24 with >15.4-fold selectivity for SIRT2, and 8 with 6.8- and 5.3-fold selectivity for SIRT3 versus SIRT1 and SIRT2, respectively. In vitro cytotoxicity studies with these compounds as well as EX527, a potent and selective SIRT1 inhibitor, suggest that antilymphoma activity of this compound class. may be predominantly due to SIRT2 inhibition.

  DOI：

  10.1021/jm4018064

文献信息

• Pd(0)-Catalyzed intramolecular arylative dearomatization of β-naphthols
  作者：Ren-Qi Xu、Ping Yang、Shu-Li You

  DOI：10.1039/c7cc04022a

  日期：——

  arylative dearomatization of β-naphthols is described. Using Q-Phos as a ligand, the arylative dearomatization reaction proceeded smoothly affording excellent yields and chemoselectivity even when the catalyst loading was reduced to 0.1 mol%. This method offers an efficient access to a series of structurally diverse spirocarbocycles. Preliminary investigation indicates that an enantioselective reaction

  描述了一种有效的Pd（0）催化的β-萘酚分子内芳基脱芳香化反应。使用Q-Phos作为配体，即使当催化剂载量降低至0.1mol％时，芳基脱芳香化反应也可顺利进行，从而提供优异的收率和化学选择性。该方法提供了对一系列结构不同的螺碳环化合物的有效访问。初步研究表明，在手性亚磷酰胺配体存在下，对映选择性反应是可行的。
• Atroposelective Synthesis of Triaryl α‐Pyranones with 1,2‐Diaxes by N‐Heterocyclic Carbene Organocatalysis
  作者：Simiao Zhang、Xiaoxue Wang、Li‐Li Han、Jibin Li、Zheng Liang、Donghui Wei、Ding Du

  DOI：10.1002/anie.202212005

  日期：2022.12.23

  The single-step atroposelective construction of triaryl α-pyranones with stereogenic 1,2-diaxes was accomplished by NHC organocatalysis. The structure of the substrates and the catalytic system play a critical role in the success of this protocol. DFT calculations were performed to rationalize the origin of the high stereoselectivity.

  通过 NHC 有机催化完成了具有立体异构 1,2-二轴的三芳基 α-吡喃酮的单步阻转选择性构建。底物的结构和催化系统对该协议的成功起着至关重要的作用。进行 DFT 计算以合理化高立体选择性的起源。
• IRE-1A Inhibitors
  申请人：MannKind Corporation

  公开号：EP2520561A1

  公开（公告）日：2012-11-07

  Methods of treating disorders associated with unfolded protein response and methods of inhibiting IRE-1α activity are provided.

  提供了治疗与未折叠蛋白反应有关的疾病的方法和抑制 IRE-1α 活性的方法。
• Atropoenantioselective Redox-Neutral Amination of Biaryl Compounds through Borrowing Hydrogen and Dynamic Kinetic Resolution
  作者：Jianwei Zhang、Jian Wang

  DOI：10.1002/anie.201711126

  日期：2018.1.8

  triggered by a cascade of borrowing hydrogen and dynamic kinetic resolution under the cooperative catalysis of a chiral iridium complex and an achiral Brønsted acid. This protocol features broad substrate scope and good functional‐group tolerance, and allows the rapid assembly of axially chiral biaryl compounds in good to high yields and with high to excellent enantioselectivity.

  我们在此报告了一种新颖的对芳基化合物的新型对苯二酚选择性氧化还原中性胺化反应，该反应是由手性铱配合物和非手性布朗斯台德酸的协同催化下的借入氢和动态动力学拆分级联触发的。该方案具有广泛的底物范围和良好的官能团耐受性，并允许以高至高收率和高至优异的对映选择性快速组装轴向手性联芳基化合物。
• Development of Pyrazolone and Isoxazol-5-one Cambinol Analogues as Sirtuin Inhibitors
  作者：Sumit S. Mahajan、Michele Scian、Smitha Sripathy、Jeff Posakony、Uyen Lao、Taylor K. Loe、Vid Leko、Angel Thalhofer、Aaron D. Schuler、Antonio Bedalov、Julian A. Simon

  DOI：10.1021/jm4018064

  日期：2014.4.24

  Sirtuins are a family of NAD+-dependent protein deacetylases that play critical roles in epigenetic regulation, stress responses, and cellular aging in eukaryotic cells. In an effort to identify small molecule inhibitors of sirtuins for potential use as chemotherapeutics as well as tools to modulate sirtuin activity, we previously identified a nonselective sirtuin inhibitor called cambinol (IC50 approximate to 50 mu M for SIRT1 and SIRT2) with in vitro and in vivo antilymphoma activity. In the current study, we used saturation transfer difference (STD) NMR experiments with recombinant SIRT1 and 20 to map parts of the inhibitor that interacted with the protein. Our ongoing efforts to optimize cambinol analogues for potency and selectivity have resulted in the identification of isoform selective analogues: 17 with >7.8-fold selectivity for SIRT1, 24 with >15.4-fold selectivity for SIRT2, and 8 with 6.8- and 5.3-fold selectivity for SIRT3 versus SIRT1 and SIRT2, respectively. In vitro cytotoxicity studies with these compounds as well as EX527, a potent and selective SIRT1 inhibitor, suggest that antilymphoma activity of this compound class. may be predominantly due to SIRT2 inhibition.