(benzo[b]thiophen-3-yl)trimethylstannane | 189366-54-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: (benzo[b]thiophen-3-yl)trimethylstannane
• 英文别名: 3-(trimethylstannyl)-benzothiophene；3-trimethylstannylbenzothiophene；1-Benzothiophen-3-yl(trimethyl)stannane
• CAS: 189366-54-9
• 化学式: C₁₁H₁₄SSn
• 分子量: 297.008
• InChiKey: VWPSDGKJLQCNHJ-UHFFFAOYSA-N

物化性质

• 沸点：
  306.8±34.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  (benzo[b]thiophen-3-yl)trimethylstannane 在 bis-triphenylphosphine-palladium(II) chloride 、 碘 、 氧气 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 15.0h， 生成 quinoxalo[6,5-b:7,8-b']bis[1]benzothiophene
  参考文献：
  名称：

  Synthesis, Crystal Structures, and Electronic Properties of Nonlinear Fused Thienoacene Semiconductors

  摘要：

  Two fused thienoacene compounds with two-dimensional ring connectivity were synthesized, and their semiconducting properties were characterized. Both compounds have a crystal structure comprised of herringbone arrays of tight pi-pi stacks. Strong pi-pi interactions lead to self-assembly into well-defined crystalline thin films from the vapor phase for both compounds. Field effect transistors were fabricated, affording identical hole mobilities of 3.0 x 10(-3) cm(2)/(V s) and l(on/off) > 10(5).

  DOI：

  10.1021/ol202662s
• 作为产物：
  描述：

  3-溴苯并噻吩 、 三甲基氯化锡 在 n-BuLi 作用下， 以 乙醚 为溶剂， 以54%的产率得到(benzo[b]thiophen-3-yl)trimethylstannane
  参考文献：
  名称：

  Electronic Influence of the Thienyl Sulfur Atom on the Oligomerization of Ethylene by Cobalt(II) 6-(Thienyl)-2-(imino)pyridine Catalysis

  摘要：

  The position of the sulfur atom in the thienyl group of 6-(thienyl)-2-(imino)pyridine ligands strongly affects the catalytic activity of the corresponding tetrahedral high-spin dihalide Co-II complexes in the oligomerization of ethylene to alpha-olefins upon activation with methylaluminoxane (MAO). Complexes with the sulfur atom in the 3-position of the thienyl ring catalyze the selective conversion of ethylene to 1-butene, while catalysts containing thien-2-yl groups give C-4-C-14 alpha-olefins. In situ EPR experiments showed the occurrence of a spin state changeover with the formation of low-spin Co-II species upon activation of the catalyst precursors by MAO. DFT calculations suggest that only thien-2-yl rings allow for the coordination of the sulfur atom to the cobalt center in the MAO-activated systems.

  DOI：

  10.1021/om0609665

文献信息

• Novel Pentacyclic p-Conjugated Cations Containing Both Heteroaromatic Units and a Tropylium Ion 2. Synthesis of Cyclohepta[a]benzofuro[c]naphthalenylium and Cyclohepta[a]benzothieno[c]-naphthalenylium Ions
  作者：Kimiaki Yamamura、Taihei Yamane、Hideki Takagi、Hideyoshi Miyake

  DOI：10.3987/com-96-7686

  日期：——

  Two isomeric pairs of cyclohepta[a]benzofuro[c]naphthalenylium ions (5 and 7) and cyclohepta[a]benzothieno[c]naphthalenylium ions (10 and 11) have been synthesized by an intramolecular Friedel-Crafts type reaction of o-benzofurylcycloheptatrienylbenzenes (3 and 8) and o-benzothienylcycloheptatrienylbenzenes (14 and 15), respectively, in a one-pot reaction.
• Electronic Influence of the Thienyl Sulfur Atom on the Oligomerization of Ethylene by Cobalt(II) 6-(Thienyl)-2-(imino)pyridine Catalysis
  作者：Claudio Bianchini、Dante Gatteschi、Giuliano Giambastiani、Itzel Guerrero Rios、Andrea Ienco、Franco Laschi、Carlo Mealli、Andrea Meli、Lorenzo Sorace、Alessandro Toti、Francesco Vizza

  DOI：10.1021/om0609665

  日期：2007.1.1

  The position of the sulfur atom in the thienyl group of 6-(thienyl)-2-(imino)pyridine ligands strongly affects the catalytic activity of the corresponding tetrahedral high-spin dihalide Co-II complexes in the oligomerization of ethylene to alpha-olefins upon activation with methylaluminoxane (MAO). Complexes with the sulfur atom in the 3-position of the thienyl ring catalyze the selective conversion of ethylene to 1-butene, while catalysts containing thien-2-yl groups give C-4-C-14 alpha-olefins. In situ EPR experiments showed the occurrence of a spin state changeover with the formation of low-spin Co-II species upon activation of the catalyst precursors by MAO. DFT calculations suggest that only thien-2-yl rings allow for the coordination of the sulfur atom to the cobalt center in the MAO-activated systems.
• Synthesis, Crystal Structures, and Electronic Properties of Nonlinear Fused Thienoacene Semiconductors
  作者：Hayden T. Black、Shubin Liu、Valerie Sheares Ashby

  DOI：10.1021/ol202662s

  日期：2011.12.16

  Two fused thienoacene compounds with two-dimensional ring connectivity were synthesized, and their semiconducting properties were characterized. Both compounds have a crystal structure comprised of herringbone arrays of tight pi-pi stacks. Strong pi-pi interactions lead to self-assembly into well-defined crystalline thin films from the vapor phase for both compounds. Field effect transistors were fabricated, affording identical hole mobilities of 3.0 x 10(-3) cm(2)/(V s) and l(on/off) > 10(5).