(4-methoxynaphthalen-1-yl)(4-methoxyphenyl)sulfane | 934845-08-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (4-methoxynaphthalen-1-yl)(4-methoxyphenyl)sulfane
• 英文别名: 1-Methoxy-4-(4-methoxyphenyl)sulfanyl-naphthalene；1-methoxy-4-(4-methoxyphenyl)sulfanylnaphthalene
• CAS: 934845-08-6
• 化学式: C₁₈H₁₆O₂S
• 分子量: 296.39
• InChiKey: RCDVPXFVOHNMJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-methoxynaphthalen-1-yl)(4-methoxyphenyl)sulfane 在 potassium peroxymonosulfate 、 三溴化硼 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 36.3h， 生成 4-[(4-methoxyphenyl)sulfonyl]naphthol
  参考文献：
  名称：

  Design, Synthesis, and Structure–Activity Relationship of N-Arylnaphthylamine Derivatives as Amyloid Aggregation Inhibitors

  摘要：

  Dyes like CR are able to inhibit the aggregation of A beta fibrils. Thus, a screening of a series of dyes including ABBB (1) was performed. Its main component 2 tested in an in vitro assay (i.e., ThT assay) showed good potency at inhibiting fibrils association. Congeners 4-9 have been designed and synthesized as inhibitors of A beta aggregation. A nurnber of these newly synthesized compounds have been found to be active in the ThT assay with IC50 of 1-57.4 mu M. The most potent compound of this series, 4k, showed micromolar activity in this test. Another potent derivative 4q (IC50 = 5.6 mu M) rapidly crossed the blood-brain barrier, achieving whole brain concentrations higher than in plasma. So 4q could be developed to find novel potent antiaggregating beta A agents useful in Alzheimer disease as well as other neurological diseases characterized by deposits of amyloid aggregates.

  DOI：

  10.1021/jm301105m
• 作为产物：
  描述：

  1-甲氧基萘 在 三氟甲磺酸酐 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 14.5h， 生成 (4-methoxynaphthalen-1-yl)(4-methoxyphenyl)sulfane
  参考文献：
  名称：

  使用亚砜的芳烃的无金属CH硫芳基化反应：直接的，一般的二芳基硫醚合成

  摘要：

  使用甲基亚砜的芳烃和杂芳烃的无金属CH硫芳基化反应，构成了合成高价值二芳基硫醚的一般无金属方案。芳烃和杂芳烃与...的偶联

  DOI：

  10.1039/c6cc07627k

文献信息

• Regioselective C–H Thioarylation of Electron-Rich Arenes by Iron(III) Triflimide Catalysis
  作者：Amy C. Dodds、Andrew Sutherland

  DOI：10.1021/acs.joc.1c00448

  日期：2021.4.16

  iron(III) triflimide allowed the efficient thiolation of a range of arenes, including anisoles, phenols, acetanilides, and N-heterocycles. The method was applicable for the late-stage thiolation of tyrosine and tryptophan derivatives and was used as the key step for the synthesis of pharmaceutically relevant biaryl sulfur-containing compounds such as the antibiotic dapsone and the antidepressant vortioxetine

  描述了一种使用铁（III）催化制备不对称联芳基硫化物的温和区域选择性方法。的活化ñ -使用强大的路易斯酸铁（III）三氟甲（芳硫基）琥珀酰亚胺允许的范围芳烃，包括苯甲醚，酚，乙酰苯胺的有效硫醇化，并Ñ -heterocycles。该方法适用于酪氨酸和色氨酸衍生物的后期硫醇化，并用作合成药学上相关的联芳基含硫化合物（如抗生素氨苯砜和抗抑郁药vortioxetine）的关键步骤。动力学研究表明，当N带有电子缺陷芳烃的-（芳硫基）琥珀酰亚胺完全由三氟甲磺酸铁（III）催化硫代芳基化，带有富电子芳烃的N-（芳硫基）琥珀酰亚胺表现出路易斯基本产物促进的自催化机理。
• Thiol Activation toward Selective Thiolation of Aromatic C–H Bond
  作者：Jing-Hao Wang、Tao Lei、Hao-Lin Wu、Xiao-Lei Nan、Xu-Bing Li、Bin Chen、Chen-Ho Tung、Li-Zhu Wu

  DOI：10.1021/acs.orglett.0c01050

  日期：2020.5.15

  Direct C-S bond coupling is an attractive way to construct aryl sulfur ether, a building block for a variety of biological active molecules. Herein, we disclose an effective model for regioselective thiolation of the aromatic C-H bond by thiol activation instead of arene activation. Strikingly, this method has been applied into anisole derivatives that are not available in the arene activation approach

  直接CS键偶联是构建芳基硫醚的一种有吸引力的方法，芳基硫醚是多种生物活性分子的基础。在这里，我们公开了通过硫醇活化而不是芳烃活化对芳香族CH键进行区域选择性硫醇化的有效模型。引人注目的是，该方法已被应用到芳烃活化方法中无法获得的苯甲醚衍生物中，从而形成具有高反应活性的单一硫醚异构体。
• Metal- and solvent-free direct C–H thiolation of aromatic compounds with sulfonyl chlorides
  作者：Feng Zhao、Qi Tan、Dahan Wang、Guo-Jun Deng

  DOI：10.1039/c9gc03384j

  日期：——

  A simple, efficient and green method for the direct thiolation of aromatic compounds using commercially available sulfonyl chlorides as the sulfur source was developed under metal- and solvent-free conditions. The C–S bond was constructed via direct C–H functionalization of diverse aromatic compounds under an oxygen atmosphere. In this process, various diaryl sulfides were synthesized in moderate to

  在无金属和无溶剂条件下，开发了一种简单，有效且绿色的方法，可使用市售的磺酰氯作为硫源直接进行芳族化合物的硫醇化。C–S键是通过在氧气气氛下将各种芳族化合物直接进行C–H官能化而构建的。在此过程中，以中等至极好的收率合成了各种二芳基硫醚。该协议显示了广泛的底物范围和良好的官能团耐受性。此外，还进行了克规模的实验，以证明该方法用于放大合成二芳基硫醚的前景。机理研究表明，该程序可能会经历一个根本性的途径。
• Naphthyl Derivatives as Inhibitors of Beta-Amyloid Aggregation
  申请人：Minetti Patrizia

  公开号：US20080255232A1

  公开（公告）日：2008-10-16

  Compounds useful in the treatment of disorders characterized by deposits of amyloid aggregates are herein described together with pharmaceutical compounds containing the same. In particular the compounds of the present invention are those having the Formula (I) as reported below, where the radicals have the meaning indicated in the description.

  本文描述了用于治疗由淀粉样聚集物沉积所特征化的疾病的化合物，以及含有相同化合物的药物化合物。特别是，本发明的化合物是具有下面报告的式（I）的化合物，其中基团具有描述中所示的含义。
• WO2007/45593
  申请人：——

  公开号：——

  公开（公告）日：——