(2-bromophenyl)(naphthalen-2-yl)sulfane | 15861-51-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (2-bromophenyl)(naphthalen-2-yl)sulfane
• 英文别名: 2-(2-Bromophenyl)sulfanylnaphthalene
• CAS: 15861-51-5
• 化学式: C₁₆H₁₁BrS
• 分子量: 315.233
• InChiKey: AHLXDBVPSJIVCN-UHFFFAOYSA-N

物化性质

• 沸点：
  411.0±28.0 °C(Predicted)
• 密度：
  1.49±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  18
• 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：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2-bromophenyl)(naphthalen-2-yl)sulfane 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium phosphate 、 双氧水 、 potassium acetate 、 铜 作用下， 以 1,4-二氧六环 、 甲醇 、 异丙醇 为溶剂， 反应 60.0h， 生成
  参考文献：
  名称：

  过渡金属配合物、聚合物、混合物、组合物及有机电子器件

  摘要：

  本发明公开了一种过渡金属配合物、聚合物、混合物、组合物及有机电子器件。按照本发明所述的过渡金属配合物，作为发光层掺杂材料，用于有机电子器件，特别是OLED中时，能提高器件的发光效率和寿命。

  公开号：

  CN113024607A
• 作为产物：
  描述：

  2-萘硫醇 、 2-溴苯基硼酸 在 2,2'-联吡啶 、 nickel(II) chloride hexahydrate 、 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 12.08h， 以86%的产率得到(2-bromophenyl)(naphthalen-2-yl)sulfane
  参考文献：
  名称：

  室温镍催化的芳基硼酸与硫酚的交叉偶联：二芳基硫醚的合成

  摘要：

  已经开发了NiCl 2 / 2,2'-联吡啶催化的硫代酚与芳基硼酸的交叉偶联，用于在室温和空气中合成对称和不对称的二芳基硫化物。该方法学可靠，为芳基硫醚的合成提供了温和且易于操作的方法，芳基硫醚是在制药和农业行业中应用的必不可少的化合物。该方法避免了使用昂贵的过渡金属，例如Pd，Ir或Rh，复杂的配体和高温。它还具有广泛的底物范围（55个示例），并提供了良率至良率（72-93％）的产品。

  DOI：

  10.1039/d0ob00244e

文献信息

• Iodine‐Promoted Tunable Synthesis of 2‐Naphthyl Thioethers and 1‐Naphthyl Thioethers
  作者：Yishu Bao、Xiuqin Yang、Zonghao Dai、Suyu Ji、Qingfa Zhou、Fulai Yang

  DOI：10.1002/adsc.201801562

  日期：2019.4.23

  An iodine‐promoted regioselective sulfenylation/deoxygenation/aromatization reaction of 1‐tetralones with disulfides has been developed. This process could be modified to synthesize 2‐naphthyl thioethers and 1‐naphthyl thioethers in moderate to excellent yields, respectively. Furthermore, when the reaction was extended to 2‐tetralones, 2‐naphthyl thioethers were obtained as the sole products. The current

  已经开发了碘促进的1-四氢萘酮与二硫化物的区域选择性亚磺酰基化/脱氧/芳香化反应。可以修改此过程以分别以中等至极好的收率合成2-萘硫醚和1-萘硫醚。此外，当反应扩展至2-四氢萘酮时，仅获得2-萘基硫醚。当前的研究桥接了酮的脱氧和亚磺酰化/芳香化，从而为有机合成提供了新的工具。
• Synthesis of Diverse <i>o</i>-Arylthio-Substituted Diaryl Ethers by Direct Oxythiolation of Arynes with Diaryl Sulfoxides Involving Migratory <i>O</i>-Arylation
  作者：Tsubasa Matsuzawa、Keisuke Uchida、Suguru Yoshida、Takamitsu Hosoya

  DOI：10.1021/acs.orglett.7b02599

  日期：2017.10.20

  A diverse range of o-arylthio-substituted diaryl ethers has been synthesized by direct oxythiolation of arynes with diaryl sulfoxides that involves the formation of the C–O and C–S bonds followed by migratory O-arylation.

  通过芳烃与二芳基亚砜的直接氧硫醇化反应，合成了各种各样的邻芳基硫基取代的二芳基醚，涉及到形成C-O和C-S键，然后进行迁移性O-芳基化。
• Cyclic Sulfoximine and Sulfonimidamide Derivatives by Copper‐Catalyzed Cross‐Coupling Reactions with Elemental Sulfur
  作者：Peng Wu、Jas S. Ward、Kari Rissanen、Carsten Bolm

  DOI：10.1002/adsc.202201408

  日期：2023.2.21

  cross-coupling reactions of α-bromoaryl NH-sulfoximines with elemental sulfur lead to benzo[d][1,3,2]dithiazole-1-oxides, which represent a new class of three-dimensional heterocycles. The reactions proceed under mild conditions showing good functional group and heterocycle tolerance. By imination/oxidation, the initial cross-coupling products can be converted to unprecedented cyclic sulfonimidamides

  铜催化的 α-溴芳基N H-亚砜亚胺与元素硫的交叉偶联反应生成苯并 [ d ][1,3,2] 二噻唑 -1-氧化物，它代表了一类新的三维杂环。反应在温和的条件下进行，显示出良好的官能团和杂环耐受性。通过亚胺化/氧化，最初的交叉偶联产物可以转化为前所未有的环状磺酰亚胺衍生物。此外，通过钌催化的与丙炔酸乙酯的环扩展获得了七元杂环。
• Photostimulated reactions of o-dihalobenzenes with nucleophiles derived from the 2-naphthyl system. Competition between electron transfer, fragmentation, and ring closure reactions
  作者：Maria T. Baumgartner、Adriana B. Pierini、Roberto A. Rossi

  DOI：10.1021/jo00061a040

  日期：1993.4

  The photostimulated reaction of o-dihalobenzenes 2 with 2 naphthoxide ions 1-O gave the substitution product on carbon 1 of the naphthyl moiety with retention of halogen (1, Br, and Cl) 3 as well as the ring closure product benzo[b]naphtho[1,2-d]furan (4), with product 3 being an intermediate in the formation of 4. The products obtained in the photostimulated reaction of 2-naphthalenethiolate ions 1-S with 2 depend on the halogens. When both nucleofugal groups are iodine, only the ring closure product benzo[b]naphtho[1,2-d]thiophene (10) is obtained. With o-bromoiodobenzene, the photostimulated reaction gave 10 and the substitution product on sulfur with retention of bromine, while with o-chloroiodobenzene the only observed product was the substitution product on sulfur with retention of chlorine. The photostimulated reaction of 2 with 2-naphthaleneselenolate ions 1-Se gave the same amount of cyclized product benzo[b]naphtho[1,2-d]selenophene (14) and the substitution product on selenium without retention of halogen 15, although in an overall low yield. It is suggested that all these reactions occur by the S(RN)1 mechanism. Theoretical studies support the different behavior found with the nucleophiles derived from the 2-naphthyl system.