α-naphtyl-3 benzothiophene | 55712-59-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: α-naphtyl-3 benzothiophene
• 英文别名: 3-α-naphthylbenzothiophene；3-(1'-naphthyl)benzothiophene；3-(naphthalene-1-yl)benzo[b]thiophene；3-(1-naphthyl)benzo[b]thiophene；3-[1]naphthyl-benzo[b]thiophene；3-[1]Naphthyl-benzo[b]thiophen；Benzo[b]thiophene, 3-(1-naphthalenyl)-；3-naphthalen-1-yl-1-benzothiophene
• CAS: 55712-59-9
• 化学式: C₁₈H₁₂S
• 分子量: 260.359
• InChiKey: CAGYGRIXMCDCLU-UHFFFAOYSA-N

物化性质

• 熔点：
  90-92 °C
• 沸点：
  433.9±24.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  α-naphtyl-3 benzothiophene 以 苯 为溶剂， 反应 8.0h， 生成 N-propyl-9-thiapentacyclo[9.7.1.02,10.03,8.015,19]nonadeca-1(18),3,5,7,11,13,15(19),16-octaen-10-amine
  参考文献：
  名称：

  Photoreactivite de systemes hexatrieniques heterocycliques. Aryl-2 et 3 benzo[b]thiophene

  摘要：

  DOI：

  10.1016/s0040-4020(01)97718-x
• 作为产物：
  描述：

  reactif de Grignard du bromo-3 benzothiophene 在 sulfur 作用下， 反应 0.25h， 生成 α-naphtyl-3 benzothiophene
  参考文献：
  名称：

  Photoreactivite de systemes hexatrieniques heterocycliques. Aryl-2 et 3 benzo[b]thiophene

  摘要：

  DOI：

  10.1016/s0040-4020(01)97718-x

文献信息

• Room-Temperature Direct β-Arylation of Thiophenes and Benzo[<i>b</i>]thiophenes and Kinetic Evidence for a Heck-type Pathway
  作者：Chiara Colletto、Saidul Islam、Francisco Juliá-Hernández、Igor Larrosa

  DOI：10.1021/jacs.5b12242

  日期：2016.2.10

  The first example of a regioselective β-arylation of benzo[b]thiophenes and thiophenes at room temperature with aryl iodides as coupling partners is reported. This methodology stands out for its operational simplicity: no prefunctionalization of either starting material is required, the reaction is insensitive to air and moisture, and it proceeds at room temperature. The mild conditions afford wide

  报道了苯并[b]噻吩和噻吩在室温下以芳基碘作为偶联伙伴的区域选择性β-芳基化的第一个例子。这种方法因其操作简单而突出：不需要任何一种起始材料的预官能化，反应对空气和水分不敏感，并且在室温下进行。温和的条件提供了广泛的官能团耐受性，通常具有完全的区域选择性和高产率，从而形成高效的催化系统。包括 13C 和 2H KIE 在内的初步机理研究表明，该过程是通过噻吩双键上的协同碳钯化作用发生的，然后是碱基辅助的抗消除作用。
• Ag(I)–C–H Activation Enables Near-Room-Temperature Direct α-Arylation of Benzo[<i>b</i>]thiophenes
  作者：Chiara Colletto、Adyasha Panigrahi、Jaime Fernández-Casado、Igor Larrosa

  DOI：10.1021/jacs.8b05361

  日期：2018.8.1

  first example of near-room-temperature α-arylation of benzo[b]thiophenes is reported. The discovery rests on the observation of a switch in α-/β-regioselectivity at different loadings of Pd2(dba)3·CHCl3 in the coupling between benzo[b]thiophene and 4-iodotoluene. We show that this unprecedented regioselectivity switch is driven by a Ag(I)-mediated C–H activation at the α-C–H position, which becomes the

  报道了苯并[b]噻吩在接近室温下α-芳基化的第一个例子。该发现基于对苯并[b]噻吩和4-碘甲苯偶联中不同负载量的Pd2(dba)3·CHCl3的α-/β-区域选择性转换的观察。我们表明，这种前所未有的区域选择性转换是由 α-C-H 位置的 Ag(I) 介导的 C-H 激活驱动的，这成为低浓度 Pd 下的主要反应模式。已经进行了支持这种机制的竞争实验、动力学研究、KIE 和 D/H 加扰实验。
• Selective Palladium-Catalysedipso Arylation of α,α-Disubstituted Benzo[b]thien-2-ylmethanols with Aryl Bromides using PCy3 as Ligand
  作者：A. Beatrix Bíró、András Kotschy

  DOI：10.1002/ejoc.200600929

  日期：2007.3

  α,α-Diphenylbenzo[b]thien-2-ylmethanol was treated with a series of aryl bromides in the presence of palladium(II) acetate and tricyclohexylphosphane to give the appropriate 2-aryl-benzo[b]thiophenes in good to excellent yield with concomitant formation of benzophenone. The reaction wassuccessfully extended to α,α-diphenylbenzo[b]thien-3-ylmethanol, although in certain cases the transformation was

  α,α-二苯基苯并[b]噻吩-2-基甲醇在乙酸钯（II）和三环己基膦存在下用一系列芳基溴化物处理，得到合适的2-芳基-苯并[b]噻吩，收率良好至极好伴随着二苯甲酮的形成。该反应成功地扩展到 α,α-二苯基苯并[b]噻吩-3-基甲醇，尽管在某些情况下，由于同时进行的邻芳基化而使转化有偏差。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Completely Regioselective Direct C–H Functionalization of Benzo[<i>b</i>]thiophenes Using a Simple Heterogeneous Catalyst
  作者：Dan-Tam D. Tang、Karl D. Collins、Frank Glorius

  DOI：10.1021/ja403130g

  日期：2013.5.22

  The first completely selective C3 C-H arylation of benzo[b]thiophenes is reported, demonstrating previously unexploited reactivity of palladium. Benzo[b]thiophenes are coupled with readily available aryl chlorides using a ligand-free, dual catalytic system of heterogeneous Pd/C and CuCl. The reaction is operationally simple and insensitive to air and moisture, and it provides valuable products with complete selectivity. Significant investigations into the nature of the active catalytic species and mechanistic considerations are discussed.
• Preparation of 3-Arylthianaphthenes^1,2
  作者：ROBERT D. SCHUETZ、LEON CIPORIN

  DOI：10.1021/jo01096a014

  日期：1958.2