thiophen-3-yl octyl ketone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: thiophen-3-yl octyl ketone
• 英文别名: 1-(thiophen-3-yl)nonan-1-one；3-nonanoylthiophene；1-Thiophen-3-ylnonan-1-one
• 化学式: C₁₃H₂₀OS
• 分子量: 224.367
• InChiKey: HHBIFGMSUPCZCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  thiophen-3-yl octyl ketone 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到2,5-dibromothiophen-3-yl octyl ketone
  参考文献：
  名称：

  Benzodithiophene-thiophene-based photovoltaic polymers with different side-chains

  摘要：

  A series of benzodithiophene-thiophene-based alternating copolymers were synthesized with different side-chains, and their photovoltaic characteristics were examined. The choice of solubilizing side-chains influences significantly the chain conformation, frontier orbital energy levels, intermolecular organization, and the resulting optical, morphological, and photovoltaic properties. The incorporation of an e-withdrawing carbonyl group in the side-chain decreased the highest occupied molecular orbital (HOMO, ca. -5.4 eV) level and improved the chain planarity through intrachain hydrogen bonding. The shortest - stacking distance (3.72 angstrom) was also measured for the alkylcarbonyl-substituted BDTCOT:PC71BM blended film by two dimensional grazing incidence X-ray scattering. With compared to other polymers, the BDTCOT:PC71BM device showed a substantially improved open-circuit voltage and short-circuit current density, leading to a 4.66% power conversion efficiency. The side-chains need to be designed to be multifunctional to induce a deep HOMO level and chain planarity (for interchain ordering) as well as good solution processability. (c) 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 854-862

  DOI：

  10.1002/pola.27516
• 作为产物：
  描述：

  2-octyl-2-(thiophen-3-yl)-1,3-dithiane 在 三氟化硼乙醚 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 以90%的产率得到thiophen-3-yl octyl ketone
  参考文献：
  名称：

  一锅脱硫-氟化-溴化。2,5-二溴-3-（1,1-二氟烷基）噻吩的合成

  摘要：

  据报道，一种独特的一锅高产率的脱硫-氟化-溴化反应可合成2,5-二溴-3-（1,1-二氟烷基）噻吩。单个二硫杂环戊烷反应物可用于生产具有更长烷基链的2，5-二溴-3-（1,1-二氟烷基）噻吩和3-（1,1-二氟烷基）噻吩。

  DOI：

  10.1021/ol101907k

文献信息

• Chemoselective Rhodium-Catalyzed Borylation of Bromoiodoarenes Under Mild Conditions
  作者：Anthony J. Varni、Michael V. Bautista、Kevin J.T. Noonan

  DOI：10.1021/acs.joc.0c00178

  日期：2020.5.15

  developed for the preparation of aryl boronate esters. The reaction proceeds under mild conditions with excellent selectivity for C-I bonds in bromoiodoarenes and exhibits broad functional group tolerance. This procedure can act as a complementary approach toward bifunctional arenes along with other metal-catalyzed borylations. Additionally, the reaction's utility in the preparation of monomers for metal-catalyzed

  已经开发了化学选择性的铑催化的硼化来制备芳基硼酸酯。该反应在温和的条件下进行，对溴代碘代芳烃中的CI键具有出色的选择性，并且具有宽泛的官能团耐受性。该方法可以作为双官能团与其他金属催化的硼烷基化反应的补充方法。另外，证明了该反应在制备用于金属催化的交叉偶联聚合的单体中的效用。
• Verlhac; Blanchard; Brisset, Journal de Chimie Physique et de Physico-Chimie Biologique, <hi>1998</hi>, vol. 95, # 6, p. 1274 - 1277
  作者：Verlhac、Blanchard、Brisset、Roncali

  DOI：——

  日期：——
• Benzodithiophene-thiophene-based photovoltaic polymers with different side-chains
  作者：Thanh Luan Nguyen、Seyeong Song、Seo-Jin Ko、Hyosung Choi、Ji-Eun Jeong、Taehyo Kim、Sungu Hwang、Jin Young Kim、Han Young Woo

  DOI：10.1002/pola.27516

  日期：2015.4.1

  A series of benzodithiophene-thiophene-based alternating copolymers were synthesized with different side-chains, and their photovoltaic characteristics were examined. The choice of solubilizing side-chains influences significantly the chain conformation, frontier orbital energy levels, intermolecular organization, and the resulting optical, morphological, and photovoltaic properties. The incorporation of an e-withdrawing carbonyl group in the side-chain decreased the highest occupied molecular orbital (HOMO, ca. -5.4 eV) level and improved the chain planarity through intrachain hydrogen bonding. The shortest - stacking distance (3.72 angstrom) was also measured for the alkylcarbonyl-substituted BDTCOT:PC71BM blended film by two dimensional grazing incidence X-ray scattering. With compared to other polymers, the BDTCOT:PC71BM device showed a substantially improved open-circuit voltage and short-circuit current density, leading to a 4.66% power conversion efficiency. The side-chains need to be designed to be multifunctional to induce a deep HOMO level and chain planarity (for interchain ordering) as well as good solution processability. (c) 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2015, 53, 854-862
• One-Pot Desulfurative−Fluorination−Bromination. Synthesis of 2,5-Dibromo-3-(1,1-difluoroalkyl)thiophenes
  作者：Nashaat Turkman、Lingling An、Martin Pomerantz

  DOI：10.1021/ol101907k

  日期：2010.10.1

  A unique one-pot, high-yield desulfurative−fluorination−bromination reaction which leads to the synthesis of 2,5-dibromo-3-(1,1-difluoroalkyl)thiophenes is reported. A single dithiolane reactant can be used to produce both 2,5-dibromo-3-(1,1-difluoroalkyl)thiophene and 3-(1,1-difluoroalkyl)thiophene with longer alkyl chains.

  据报道，一种独特的一锅高产率的脱硫-氟化-溴化反应可合成2,5-二溴-3-（1,1-二氟烷基）噻吩。单个二硫杂环戊烷反应物可用于生产具有更长烷基链的2，5-二溴-3-（1,1-二氟烷基）噻吩和3-（1,1-二氟烷基）噻吩。