methyl 4-(2-(hex-1-ynyl)-1,3-dithiolan-2-yl)benzoate | 515139-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 4-(2-(hex-1-ynyl)-1,3-dithiolan-2-yl)benzoate
• 英文别名: Methyl 4-(2-hex-1-ynyl-1,3-dithiolan-2-yl)benzoate
• CAS: 515139-33-0
• 化学式: C₁₇H₂₀O₂S₂
• 分子量: 320.477
• InChiKey: JBKJSFBPMXCHIM-UHFFFAOYSA-N

物化性质

• 沸点：
  457.6±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  76.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-(2-(hex-1-ynyl)-1,3-dithiolan-2-yl)benzoate 在 sodium sulfide 、 正丁基锂 、 三溴化磷 、 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 苯 为溶剂， 反应 35.83h， 生成 23,74-dibutyl-4-(methylthio)-2,7(2,5)-difurana-1,3,6,8(1,4)-tetrabenzenacyclodecaphane
  参考文献：
  名称：

  Furan-Containing Oligoaryl Cyclophanene

  摘要：

  Furan-containing oligoaryl cyclophanene 1 and the corresponding cyclophane 2 were synthesized from propargylic dithioacetal 3. The electrochemical and photophysical properties and the fluxional behavior of these molecules have been examined. The emission of 1 appeared at 499 nm whereas that of 2 appeared at 389 nm.

  DOI：

  10.1021/ol0356688
• 作为产物：
  描述：

  methyl 4-(1-hydroxyhept-2-ynyl)benzoate 在 manganese(IV) oxide 作用下， 生成 methyl 4-(2-(hex-1-ynyl)-1,3-dithiolan-2-yl)benzoate
  参考文献：
  名称：

  Optical behaviors of conjugated-chain compounds containing benzene and furan units

  摘要：

  Thirteen conjugated-chain compounds which contain benzene and furan units were prepared, their optical behaviors, including UV-vis absorption coefficient (epsilon), absorption wavelengths (lambda(a)) fluorescence emission wavelengths and quantum yields (0) were measured. Meanwhile, their LUMO and HOMO energy were determined by cyclic voltammetry and their second-order polarizations (beta(xxx)) values were determined by solvatochromic method, respectively. The results showed that this kind of compounds possess a shorter lambda(a) (320-365 nm) and performance a higher (P values, especially for 2aa, 2ab, 2ac and 2bb, their Phi values are all more than 90%. These compounds, except 2db, showed a higher beta(xxx) values in DMSO, especially for 2dc (75.77 x 10(-30) m(5) C-1) and 2dd (83.32 x 10(-30) m(5) C-1), than that 10-methyl-acri done (6.578 x 10(-30) m(5) C-1) or 10-benzylacridone (6.845 x 10(-30) m(5) C-1) in DMSO did, and second harmonic generation value of 10-methylacridone and 10-benzylacridone in powder are, respectively, 1.381 and 1.861 times of that value of urea. The beta(xxx) values and Phi values determined for these compounds in this work were lower than these values which were desired in the original work, this phenomena was explained from their molecular structures. This work confirmed that as these compounds performance shorter lambda(a) and higher Phi values, they could be good blue-color optical materials for some fields, such as OLED materials, two-photo absorption materials, fluorescent dyes. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2006.05.035

文献信息

• LED based on alternating benzene-furan oligomers
  作者：Senchuan Song、Jianghan Chen、Wenlong Pan、Hucacan Song、Huahong Shi、Yuliang Mai、Wu Wen

  DOI：10.1016/j.saa.2016.07.008

  日期：2017.1

  Meanwhile, the excitation spectrum and emission spectrum of 2b and 2d in solid and in ethyl acetate were respectively recorded, the thermal stability of 2b and 2d was evaluated, and the fluorescence emission behaviors of two light emitting diodes, fabricated with 2b and 2d as phosphors, were investigated. The results showed that most of target compounds can perform high fluorescence emission ability, compounds

  通过两种不同的方法合成了一系列包含两个呋喃单元和三个以上其他芳香环单元的共轭链化合物，它们的紫外可见吸收系数（ε），最大吸收波长（λa），荧光发射波长（λe）确定了斯托克斯位移和量子产率（Φ），讨论了分子结构与光谱行为的影响之间的关系。同时，分别记录了固体和乙酸乙酯中2b和2d的激发光谱和发射光谱，评估了2b和2d的热稳定性，以及两个以2b和2d为荧光粉制造的发光二极管的荧光发射行为。 ，进行了调查。结果表明，大多数目标化合物均具有较高的荧光发射能力，化合物2b和2d在350℃下可以具有较高的热稳定性，并且它们适合于制造作为磷光体的发光二极管，用2b和2d制造的发光二极管可以显示出较高的荧光发射能力。因此，这些化合物值得进一步开发为荧光发射材料。
• Bidirectional iterative synthesis of alternating benzene–furan oligomers towards molecular wires
  作者：Chin-Fa Lee、Ching-Yuan Liu、Hua-Can Song、Shr-Jie Luo、Jui-Chang Tseng、Hsi-Hua Tso、Tien-Yau Luh

  DOI：10.1039/b207881c

  日期：——

  Reaction of propargylic dithioacetal 2a with BuLi gives the sulfur-substituted allenyllithium 3a which is allowed to react with a dialdehyde to yield the corresponding alternating benzene–furan oligoaryls 6. Functional group transformation converts the ester groups in 6 to dialdehyde 8 which can be used for the synthesis of higher homologues towards molecular wires. A combination of this furan annulation, Heck reaction and Sonogashira coupling leads to a variety of benzene–furan–alkene/alkyne conjugated oligomers of precise length.

  丙炔基二硫代乙酸酯 2a 与 BuLi 的反应生成了硫替代的丙炔基锂化合物 3a，随后与二醛反应生成相应的交替苯–呋喃低聚芳烃 6。功能基团转化将 6 中的酯基团转化为二醛 8，后者可用于合成更高 homologues 以形成分子线。结合这种呋喃环化、Heck 反应和 Sonogashira 烃偶联，能得到多种精确长度的苯–呋喃–烯/炔 conjugated 低聚物。
• Facile Synthesis of Alternating Benzene-Pyrrole Oligomers by Cyclization of Propargylic Dithioacetals and Imines and Their Fluorescent Properties
  作者：Tong-Hui Huang、Xiao-Lei Zhu、Ai-Dong Zhang、Hai-Yang Tu

  DOI：10.1002/ejoc.201100111

  日期：2011.8

  benzene–pyrrole oligomers with diverse functional groups and the elongated alternating heterocycle–benzene–pyrrole oligoaryls. The syntheses are based on a one-pot, three-step reaction of propargylic dithioacetals and imines. The subtle influence of functional groups, such as ether, ester, hydroxy, and dithiacetal groups on the peripheral benzene rings, on the reaction, has been explored and the reaction conditions

  交替的苯-杂芳基低聚物具有迷人的光电特性和广泛的应用。本文介绍了具有不同官能团的苯 - 吡咯低聚物和拉长的交替杂环 - 苯 - 吡咯低聚芳基的简便合成。该合成基于炔丙基二硫缩醛和亚胺的一锅三步反应。探索了外围苯环上的醚、酯、羟基和二硫缩醛等官能团对反应的微妙影响，并相应地改变了反应条件以达到合理的收率。伸长可以通过使用类似的程序来完成。确定了原始和延长的交替苯-吡咯低聚物的荧光特性。
• Observing Second-Order Nonlinear Optical Properties by Symmetry Breaking in Centrosymmetric Furan-Containing Oligoaryl Cyclophandienes
  作者：Hsin-Chieh Lin、Jui-Hung Hsu、Chao-Kuei Lee、Oliver Yung-Hui Tai、Chin-Hsien Wang、Chih-Ming Chou、Kuang-Yen Chen、Yi-Lin Wu、Tien-Yau Luh

  DOI：10.1002/chem.200902115

  日期：2009.12.7

  Centrosymmetric furan‐containing cyclophandienes 3 and 4, synthesized by our furan annulation protocol, have been shown to exhibit extraordinarily large Stokes shifts and second‐order nonlinear optical β values. The β values for 3 and 4 measured at 1.32 μm are 208 and 530×10−30 esu, respectively. The β values of 3 and 4 are similar to those of respective cyclophenes 1 a and 7 in which strong hyperpoarizable

  由呋喃环化方案合成的含呋喃中心对称环呋喃二酮3和4已显示出异常大的斯托克斯位移和二阶非线性光学β值。在1.32μm下测得的3和4的β值分别为208和530×10 -30  esu。3和4的β值与各自的环酚1a和7的β值相似，其中两个扭曲的π系统（寡芳基和桥连双键）之间可能发生强烈的超极化相互作用。由于共振造成的对称性破坏（参见2））和3和4的独特结构特征已用于解释这种异常的光物理行为。
• The effect of molecular conformation on single molecule conductance: measurements of π-conjugated oligoaryls by STM break junction
  作者：I-Wen Peter Chen、Ming-Dung Fu、Wei-Hsiang Tseng、Chun-hsien Chen、Chih-Ming Chou、Tien-Yau Luh

  DOI：10.1039/b705521h

  日期：——

  Measurements of molecular break junction reveal quantitatively the correlation betweeen the single-molecule conductance and the conformation of π-conjugated molecules with 6–18 conjugated double bonds.

  分子断裂连接的测量结果定量揭示了单分子电导与具有6-18个共轭双键的Β-共轭分子的构象之间的相关性。