1-(1-Benzothiophen-3-yl)naphthalene-2-carbaldehyde | 1400812-95-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(1-Benzothiophen-3-yl)naphthalene-2-carbaldehyde
• CAS: 1400812-95-4
• 化学式: C₁₉H₁₂OS
• 分子量: 288.37
• InChiKey: VOKGUQCAQJNZRA-UHFFFAOYSA-N

物化性质

• 沸点：
  495.4±38.0 °C(predicted)
• 密度：
  1.286±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(1-Benzothiophen-3-yl)naphthalene-2-carbaldehyde 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 生成 1-(1-(benzo[b]thiophen-3-yl)naphthalen-2-yl)-3-phenylprop-2-yn-1-one
  参考文献：
  名称：

  铜催化有氧氧化脱氢环化构建多环芳烃

  摘要：

  铜催化苯并[]噻吩的有氧氧化脱氢环化代表了快速构建含有苯并[]噻吩基团的多环芳烃（PAH）的有效方法。然而，这仍然是一个尚未充分探索的领域。在这里，我们建立了一种新型的铜催化苯并[]噻吩有氧氧化脱氢环化，能够利用苯并[]噻吩官能团来获得多环芳烃。该方法具有温和的反应条件、高原子经济性和显着的化学选择性，可产生多种含有苯并[]噻吩基团的多环芳烃。机理实验和DFT计算表明，原位生成的苯并噻吩自由基阳离子中间体经历了分子间环化和H2O的捕获，从而完成了氧化环芳构化反应。标记实验表明，产物中的羰基氧原子来源于反应过程中产生的H2O。

  DOI：

  10.1016/j.tetlet.2024.155040
• 作为产物：
  描述：

  在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 以42%的产率得到1-(1-Benzothiophen-3-yl)naphthalene-2-carbaldehyde
  参考文献：
  名称：

  Exploiting the π-Acceptor Properties of Carbene-Stabilized Phosphorus Centered Trications [L₃P] ³⁺: Applications in Pt(II) Catalysis

  摘要：

  Reaction of tris(dimethylaminocyclopropenium) substituted phosphine 1 with K2PtCl4 afforded the bench stable complex 3 which upon treatment with Ag[CB11H6Cl6] turned out to be an excellent catalyst for the transformation of a variety of ortho-biaryl substituted alkynes into polycyclic homo- and heteroarenes of different size, shape, and curvature through a 6-endo-dig cyclization. This constitutes the first example ever reported of using a P-1-centered trication as ligand in catalysis. The strong pi-acceptor character of 1 that derives from its three positive charges substantially increases the intrinsic pi-acidity of Pt in complex 1.PtCl2 and dramatically enhances its ability to activate pi-systems toward nucleophilic attack. As a consequence, a remarkable acceleration of the model transformation is observed when compared with other classical pi-acceptor ligands such as P(OPh)(3) or P(C6F5)(3). Moreover, the employment of 1 as ligand also expands the scope of this reaction to previously inaccessible substitution patterns. Kinetic studies and deuterium labeling experiments as well as density functional theory (DFT) calculations were performed in order to explain these findings.

  DOI：

  10.1021/ja306947m

文献信息

• NOVEL ORGANIC HETEROCYCLIC COMPOUND AND LIGHT-EMITTING DEVICE COMPRISING SAME
  申请人：SFC CO., LTD.

  公开号：US20180072753A1

  公开（公告）日：2018-03-15

  The present invention relates to an organic light-emitting compound represented by [Chemical Formula A] and an organic light-emitting device. In Chemical Formula, A, X, Y, Z, and the substituents R 1 to R 8 , and R 11 to R 20 are as defined in the specification.

  本发明涉及一种由[化学公式A]表示的有机发光化合物以及一种有机发光器件。在化学公式中，A、X、Y、Z以及取代基R1至R8和R11至R20如说明书中所定义。
• Enantioselective Synthesis of Atropisomers Featuring Pentatomic Heteroaromatics by Pd-Catalyzed C–H Alkynylation
  作者：Shuo Zhang、Qi-Jun Yao、Gang Liao、Xin Li、Han Li、Hao-Ming Chen、Xin Hong、Bing-Feng Shi

  DOI：10.1021/acscatal.8b04870

  日期：2019.3.1

  heteroarenes, including pyrroles, thiophenes, benzothiophenes, and benzofurans were compatible with this protocol. Notably, this strategy offers the catalytic asymmetric synthesis of axially chiral 3,3′-bisbenzothiophene with good ee (93% ee). Computational studies revealed the key structural elements that differentiate the rotational barriers of benzothiophene and benzofuran moieties.

  由于较低的旋转势垒，具有五元环的阻转异构体的催化不对称结构仍然是一个艰巨的挑战。在本文中，我们描述了Pd催化的对映选择性C–H炔基化反应以合成这种对映异构体。获得了一系列具有一个或什至两个五元环的立体异构C–N或C–C键的阻转异构体（产率高达98％，ee大于99％）。各种五元杂芳烃，包括吡咯，噻吩，苯并噻吩和苯并呋喃均与该方案兼容。值得注意的是，该策略提供了具有良好ee（93％ee）的轴向手性3,3'-双苯并噻吩的催化不对称合成。计算研究揭示了区分苯并噻吩和苯并呋喃部分的旋转壁垒的关键结构要素。
• Pd-Catalyzed Atroposelective C–H Allylation and Alkenylation: Access to Enantioenriched Atropisomers Featuring Pentatomic Heteroaromatics
  作者：Hao-Ming Chen、Shuo Zhang、Gang Liao、Qi-Jun Yao、Xue-Tao Xu、Kun Zhang、Bing-Feng Shi

  DOI：10.1021/acs.organomet.9b00490

  日期：2019.10.28

  The development of efficient and unified synthetic methods to access enantioenriched pentatomic biaryls is extremely challenging, due to the relatively low rotational barriers of these five-membered atropisomeric species, Described herein is a Pd-catalyzed asymmetric C-H allylation and alkenylation to prepare such atropisomers. This protocol is tolerant of various five-membered biaryls containing benzothiophenes and benzofurans, providing pentatomic biaryls with good to excellent enantioselectivities (up to 99% ee).