6-(4-(dimethylamino)phenyl)-2-methylhexa-3,5-diyn-2-ol | 91511-88-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 6-(4-(dimethylamino)phenyl)-2-methylhexa-3,5-diyn-2-ol
• 英文别名: 6-[4-(dimethylamino)phenyl]-2-methylhexa-3,5-diyn-2-ol
• CAS: 91511-88-5
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: NCJJLIUTJOJOHT-UHFFFAOYSA-N

物化性质

• 熔点：
  106 °C
• 沸点：
  375.3±42.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  23.47
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  6-(4-(dimethylamino)phenyl)-2-methylhexa-3,5-diyn-2-ol 在 sodium hydroxide 作用下， 以 甲醇 、 氯仿 、 甲苯 为溶剂， 生成 1-methyl-4-{[4-(dimethylamino)phenyl]butadiynyl}pyridinium (p-aminophenyl)sulfonate
  参考文献：
  名称：

  Synthesis of Phenylbutadiynylpyridinium Derivatives for Nonlinear Optics

  摘要：

  1- Methyl- 4-{[ 4-( dimethylamino) phenyl] butadiynyl} pyridinium ( PBP) derivatives with iodide or benzenesulfonate anion were synthesized as potential compounds for both second- and third- order NLO applications. PBP shows peculiar absorption spectrum in methanol, in which molar extinction coefficient at absorption maximum ( lambda(max)) decrease irrespective of bathochromic shift of lambda(max) compared with the corresponding compound with one triple bond between two aromatic rings. From semiempirical MO calculations, it was explained by aromatic- ring rotation of PBP in methanol. Activity on second- harmonic generation ( SHG) was found in four out of thirteen compounds synthesized. Although most of PBP derivatives were found to show exothermic reaction before melting, pure solid- state polymerization was not confirmed in these compounds.

  DOI：

  10.1080/15421400701548993
• 作为产物：
  描述：

  2,7-二甲基-3,5-辛二炔-2,7-二醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 生成 6-(4-(dimethylamino)phenyl)-2-methylhexa-3,5-diyn-2-ol
  参考文献：
  名称：

  铜催化的叠氮化物-炔烃环加成反应中的1-碘代-1,3-二炔类化合物：一步法合成4-乙炔基-5-碘-1,2,3-三唑

  摘要：

  发现使用碘化三（三苯基膦）铜（I）作为催化剂，将铜与有机叠氮化物催化碘代二乙炔与有机叠氮化物的1，3-偶极环加成反应是制备5-碘-4-乙炔基三唑的有效一步合成途径。该反应耐受丁二炔和叠氮化物部分中的各种官能团。还评估了所得的5-碘-4-乙炔基三唑的合成应用：Sonogashira与炔烃的偶联导致不对称取代的三唑稠合的二炔体系，而Suzuki反应产生了相应的5-芳基-4-乙炔基三唑。

  DOI：

  10.1021/acs.joc.8b02916

文献信息

• Tuning of cross-Glaser products mediated by substrate–catalyst polymeric backbone interactions
  作者：Sharanjeet Kaur、Aritra Mukhopadhyaya、Abdul Selim、Vijayendran Gowri、K. M. Neethu、Arif Hassan Dar、Shaifali Sartaliya、Md. Ehesan Ali、Govindasamy Jayamurugan

  DOI：10.1039/c9cc08565c

  日期：——

  Tuneable selectivity in cross-Glaser products is achieved by tweaking the catalyst-backbone. The interaction responsible for this is unravelled.

  通过调整催化剂骨架实现了交叉格拉瑟产物中的可调选择性。负责这一作用的相互作用被揭示。
• Trisulfur Radical Anion as the Key Intermediate for the Synthesis of Thiophene via the Interaction between Elemental Sulfur and NaO<i>t</i>Bu
  作者：Guoting Zhang、Hong Yi、Hong Chen、Changliang Bian、Chao Liu、Aiwen Lei

  DOI：10.1021/ol503015b

  日期：2014.12.5

  A facile base-promoted sulfur-centered radical generation mode and a single-step protocol for the synthesis of thiophene derivatives using 1,3-diynes via the interaction between elemental sulfur and NaOtBu has been reported. EPR experiments revealed that the trisulfur radical anion acts as a key intermediate of this process. A plausible mechanism has been proposed.

  据报道，一种简便的碱促进的以硫为中心的自由基生成方式和一种通过元素硫与NaO t Bu相互作用使用1,3-二炔合成噻吩衍生物的单步操作方案。EPR实验表明，三硫自由基阴离子是该过程的关键中间体。已经提出了一种合理的机制。
• Rational Design of a Palladium-Catalyzed Csp-Csp Cross-Coupling Reaction Inspired by Kinetic Studies
  作者：Yue Weng、Ben Cheng、Chuan He、Aiwen Lei

  DOI：10.1002/anie.201204112

  日期：2012.9.17

  Less is More: A highly selective Pd‐catalyzed Csp–Csp cross‐coupling reaction between terminal alkynes and 1‐bromoacetylenes has been developed. Catalyst loading is low (only 0.0001–0.01 mol % of Pd is required) and provides products with high selectivities and good to excellent yields under mild conditions. TBAB=tetrabutylammonium bromide, TON=turnover number.

  少即是多：已开发出在末端炔烃和1-溴乙炔之间具有高选择性的Pd催化的C sp -C sp交叉偶联反应。催化剂的负载量低（仅需0.0001–0.01 mol％的Pd），并且在温和条件下为产品提供了高选择性和良好至优异的收率。TBAB ＝四丁基溴化铵，TON ＝周转数。
• Design and Synthesis of New 5-aryl-4-Arylethynyl-1H-1,2,3-triazoles with Valuable Photophysical and Biological Properties
  作者：Mariia M. Efremova、Anastasia I. Govdi、Valeria V. Frolova、Andrey M. Rumyantsev、Irina A. Balova

  DOI：10.3390/molecules26092801

  日期：——

  Cu-catalyzed 1,3-dipolar cycloaddition of methyl 2-azidoacetate to iodobuta-1,3-diynes and subsequent Suzuki-Miyaura cross-coupling were used to synthesize new triazoles derivatives: 5-aryl-4-arylethynyl-1H-1,2,3-triazoles. Investigation of their optical properties by using UV absorption and fluorescence emission spectroscopies revealed that all molecules possess fluorescence properties with the values of the Stokes shift more than 100 nm. The photophysical behavior of the two most promising triazoles in polar and non-polar solvents was also studied.

  使用Cu催化的1,3-二极环加成反应将甲基2-叠氮乙酸酯与碘丁-1,3-二炔烃进行反应，然后进行Suzuki-Miyaura交叉偶联反应，用于合成新的三唑衍生物：5-芳基-4-芳基乙炔基-1H-1,2,3-三唑。通过UV吸收和荧光发射光谱研究它们的光学性质，发现所有分子均具有荧光性质，斯托克斯位移值超过100纳米。还研究了两种最有前景的三唑在极性和非极性溶剂中的光物理行为。
• Diacetylene alcohol derivatives of aromatic amines
  作者：M. I. Bardamova、I. L. Kotlyarevskii、Z. P. Trotsenko

  DOI：10.1007/bf00947827

  日期：1984.4