2-(phenylsulfonyl)-1,2,3,4-tetrahydronaphthalene | 137059-41-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-(phenylsulfonyl)-1,2,3,4-tetrahydronaphthalene
• 英文别名: (±)-1-(phenylsulfonyl)-1,2,3,4-tetrahydronaphthalene；1-(Benzenesulfonyl)-1,2,3,4-tetrahydronaphthalene
• CAS: 137059-41-7
• 化学式: C₁₆H₁₆O₂S
• 分子量: 272.368
• InChiKey: RKAHFQIMKXTHAR-UHFFFAOYSA-N

物化性质

• 熔点：
  64-65 °C
• 沸点：
  470.2±38.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-<3-(phenylsulfonyl)-3-butenyl>-1-bromobenzene 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 以88%的产率得到2-(phenylsulfonyl)-1,2,3,4-tetrahydronaphthalene
  参考文献：
  名称：

  Use of 2,3-bis(phenylsulfonyl)-1-propene as a multicoupling reagent

  摘要：

  2,3-Bis(phenylsulfonyl)-1-propene (1) reacts with various amines to afford products derived from addition across the double bond as well as S(N)2' displacement. When treated with 2-piperidinemethanol, bissulfone 1 gave the expected S(N)2' product which was converted to the corresponding bromide and cyclized with tributyltin hydride to a bicyclic amine. Reaction of bissulfone 1 with furfurylamine followed by treatment with acetyl chloride afforded the product derived from a tandem S(N)2' displacement-intramolecular Diels-Alder reaction. Several novel heterocyclic compounds were prepared by connecting two nucleophilic sites with a carbon-carbon bond and allowing this reagent to react with bissulfone 1. The reaction of 1 with the pyrrolidine enamine derived from cyclohexanone gave bicyclo[3.3.1]nonan-9-one in 78% yield. The soft nucleophile approach is not the only way to add carbon centers to bissulfone 1. Radical attack on the double bond of 1 leads to an intermediate sulfonyl-stabilized radical. This species readily fragments to produce a new vinyl sulfone which undergoes further radical cyclization to give six-membered ring sulfones.

  DOI：

  10.1021/jo00027a052

文献信息

• Cu2O-catalyzed C–S coupling of quaternary ammonium salts and sodium alkane-/arene-sulfinates
  作者：Youming Huang、Hongyi Chen、Wenting Zheng、Qingle Zeng

  DOI：10.1016/j.tetlet.2020.152320

  日期：2020.9

  Cu2O-catalyzed C–S bond cross coupling of alkane-/arene-sulfinates and (enantioenriched) benzylic quaternary ammonium salts has been developed. The product benzylic sulfones were obtained in good to high yields (75–96%). Chiral arylmethyl sulfones with high enantiomeric excess (90–94% ee) were also synthesized in the presence of Cu2O and 1,1′-bis-(diphenylphosphino)ferrocene (dppf).

  已经开发了一种新的协议，该协议通过烷烃/芳烃亚​​磺酸盐和（对映体富集的）苄基季铵盐的Cu 2 O催化的C–S键交叉偶联来合成（对映体富集的）苄基砜。获得的苄基砜产品收率良好至高（75-96％）。在Cu 2 O和1,1'-双-（二苯基膦基）二茂铁（dppf）存在下，还合成了具有高对映体过量（90-94％ee）的手性芳基甲基砜。
• Catalyst-Free Alkylation of Sulfinic Acids with Sulfonamides via sp³ C−N Bond Cleavage at Room Temperature
  作者：Cong-Rong Liu、Man-Bo Li、Dao-Juan Cheng、Cui-Feng Yang、Shi-Kai Tian

  DOI：10.1021/ol900788r

  日期：2009.6.18

  alkylation of sulfinic acids with sulfonamides has been developed via sp3 C−N bond cleavage at room temperature. In the absence of external catalysts and additives, a wide variety of N-benzylic and N-allylic sulfonamides couple with sulfinic acids to give structurally diversified sulfones in moderate to excellent yields. Furthermore, the reaction of N-(2-acyl)allylic sulfonamides with sulfinic acids provides

  通过在室温下通过sp 3 C-N键裂解，开发了一种前所未有的亚磺酸与磺酰胺的无催化剂烷基化反应。在没有外部催化剂和添加剂的情况下，各种各样的N-苄基和N-烯丙基磺酰胺与亚磺酸偶联，以中等至极好的收率得到结构多样化的砜。此外，N-（2-酰基）烯丙基磺酰胺与亚磺酸的反应提供了具有独有的Z选择性的三取代烯丙基砜的便利途径。
• An Expeditious Entry to Benzylic and Allylic Sulfones through Byproduct-Catalyzed Reaction of Alcohols with Sulfinyl Chlorides
  作者：Hai-Hua Li、De-Jun Dong、Yin-Huan Jin、Shi-Kai Tian

  DOI：10.1021/jo901974h

  日期：2009.12.18

  In the absence of external catalysts and additives, a broad range of benzylic and allylic alcohols react with various sulfinyl chlorides to afford structurally diversified benzylic and allylic sulfones in moderate to excellent yields, and importantly, a catalysis with byproduct HCl is involved in this new protocol for sulfone synthesis.