11-phenyl-10-undecyn-1-ol | 473932-31-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 11-phenyl-10-undecyn-1-ol
• 英文别名: 11-phenylundec-10-yn-1-ol
• CAS: 473932-31-9
• 化学式: C₁₇H₂₄O
• 分子量: 244.377
• InChiKey: SHDFMRVOORMRJZ-UHFFFAOYSA-N

物化性质

• 沸点：
  375.5±15.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  11-phenyl-10-undecyn-1-ol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以95%的产率得到11-phenylundecan-1-ol
  参考文献：
  名称：

  新型 Niphathesine 类似物的合成和生物学评价

  摘要：

  Niphathesine C 和相关的吡啶生物碱是众所周知的具有有趣抗菌活性的天然产物，其特征在于一个吡啶环和一个带有末端含氮官能团的亲脂侧链。本文描述了这些烷基吡啶生物碱的杂环和末端官能团变化的类似物的合成。合成的关键步骤是适当的芳基碘化物与 undec-10-ynol 或 undec-10-ynoic 酸衍生物的 Sonogashira 反应。所得化合物在琼脂扩散试验中针对几种细菌和真菌进行了测试。

  DOI：

  10.1002/ardp.200600204
• 作为产物：
  描述：

  碘苯 、 10-十一炔醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以90.7%的产率得到11-phenyl-10-undecyn-1-ol
  参考文献：
  名称：

  带有联苯侧链的双取代聚乙炔的合成，同构和发光性质

  摘要：

  包含联苯（Biph）核，烷基间隔基和烷氧基尾基（-{RC = C [（CH 2）米-OCO-的BiPh-OC 7 H ^ 15 ]} ñ - ，其中[R，米= CH 3，4 [P 1（4）]; CH 3，9 [P 1（9）]; C ^ 6 ħ 5，4 [P 2（4）];和C 6 H ^ 5，9 [P 2（9）]}，合成了间隔基长度和骨架结构对聚合物性能的影响。双取代乙炔单体[ 1（m）和2（m）（m = 4，9）]是通过联苯羧酸（6）与ω-炔醇[ 4（m）或5（m）]酯化制备的。通过WCl 6-，MoCl 5-和NbCl 5 -Ph 4进行1（m）和2（m）的聚合。Sn和WCl 6 -Ph 4 Sn催化的反应在最佳条件下可以以高收率（高达81％）生产高分子量（M w高达3.1×10 5）的聚合物P 1（m）和P 2（m））。通过核磁共振（NMR），热重分析（TGA），差示扫描量热法（DSC

  DOI：

  10.1021/ma049094d

文献信息

• Copper(0) nanoparticle catalyzed <i>Z</i> ‐Selective Transfer Semihydrogenation of Internal Alkynes
  作者：Maria Jesus Moran、Katia Martina、Vidmantas Bieliunas、Francesca Baricco、Silvia Tagliapietra、Gloria Berlier、Wim M. De Borggraeve、Giancarlo Cravotto

  DOI：10.1002/adsc.202100126

  日期：2021.6.8

  The use of copper(0) nanoparticles in the transfer semihydrogenation of alkynes has been investigated as a lead-free alternative to Lindlar catalysts. A stereo-selective methodology for the hydrogenation of internal alkynes to the corresponding (Z)-alkenes in high isolated yields (86% average) has been developed. This green and sustainable transfer hydrogenation protocol relies on non-noble copper

  已经研究了在炔烃转移半氢化中使用铜 (0) 纳米粒子作为 Lindlar 催化剂的无铅替代品。一种将内炔氢化成相应的 ( Z) 的立体选择性方法)-烯烃的高分离产率（平均 86%）已被开发出来。这种绿色且可持续的转移氢化协议依赖于非贵重铜纳米粒子来还原富电子和缺电子、脂肪族取代和芳香族取代的内部炔烃。多元醇，如乙二醇和甘油，已被证明可作为氢源，并观察到优异的立体选择性和化学选择性。无论是单独使用还是组合使用，微波和超声波辐射等辅助技术都可以增强传热和传质，从而将反应时间从几小时缩短到几分钟。
• Syntheses and Mesomorphic and Luminescent Properties of Disubstituted Polyacetylenes Bearing Biphenyl Pendants
  作者：Yuping Dong、Jacky W. Y. Lam、Han Peng、Kevin K. L. Cheuk、Hoi Sing Kwok、Ben Zhong Tang

  DOI：10.1021/ma049094d

  日期：2004.8.1

  light-emitting poly(2-alkyne)s and poly(1-phenyl-1-alkyne)s containing biphenyl (Biph) cores, alkyl spacers, and alkoxy tails (-RC=C[(CH2)m-OCO-Biph-OC7H15]}n-, where R, m = CH3, 4 [P1(4)]; CH3, 9 [P1(9)]; C6H5, 4 [P2(4)]; and C6H5, 9 [P2(9)]}, were synthesized and the effects of the spacer length and backbone structure on the properties of the polymers were investigated. The disubstituted acetylene monomers

  包含联苯（Biph）核，烷基间隔基和烷氧基尾基（-RC = C [（CH 2）米-OCO-的BiPh-OC 7 H ^ 15 ]} ñ - ，其中[R，米= CH 3，4 [P 1（4）]; CH 3，9 [P 1（9）]; C ^ 6 ħ 5，4 [P 2（4）];和C 6 H ^ 5，9 [P 2（9）]}，合成了间隔基长度和骨架结构对聚合物性能的影响。双取代乙炔单体[ 1（m）和2（m）（m = 4，9）]是通过联苯羧酸（6）与ω-炔醇[ 4（m）或5（m）]酯化制备的。通过WCl 6-，MoCl 5-和NbCl 5 -Ph 4进行1（m）和2（m）的聚合。Sn和WCl 6 -Ph 4 Sn催化的反应在最佳条件下可以以高收率（高达81％）生产高分子量（M w高达3.1×10 5）的聚合物P 1（m）和P 2（m））。通过核磁共振（NMR），热重分析（TGA），差示扫描量热法（DSC
• Access to Macrocyclic Endocyclic and Exocyclic Allylic Alcohols by Nickel-Catalyzed Reductive Cyclization of Ynals
  作者：Beth Knapp-Reed、Gireesh M. Mahandru、John Montgomery

  DOI：10.1021/ja054590i

  日期：2005.9.28

  macrocyclizations of ynals are reported. Disubstituted alkynes afford either endocyclic or exocyclic allylic alcohols depending on the ligand. Phosphine ligands favor the formation of endocyclic olefins, whereas N-heterocyclic carbene ligands favor the formation of exocyclic olefins. Terminal alkynes provide 1,2-disubstituted olefins with N-heterocyclic carbene ligands.

  报道了镍催化的 ynals 还原大环化。二取代的炔烃根据配体提供环内或环外烯丙醇。膦配体有利于形成环内烯烃，而 N-杂环卡宾配体有利于形成环外烯烃。末端炔烃提供具有 N-杂环卡宾配体的 1,2-二取代烯烃。
• Silole-Containing Polyacetylenes. Synthesis, Thermal Stability, Light Emission, Nanodimensional Aggregation, and Restricted Intramolecular Rotation
  作者：Junwu Chen、Zhiliang Xie、Jacky W. Y. Lam、Charles C. W. Law、Ben Zhong Tang

  DOI：10.1021/ma0213504

  日期：2003.2.1

  We synthesized three substituted polyacetylenes carrying 1,2,3,4,5-pentaphenylsilolyl (PS) pendants, i.e., -[HC=C(PS)](n)- (1), -HC=C[(CH2)(9)OPS]}(n)- (2) and -(C6H5)C=C[(CH2)(9)OPS]} (n)- (3), and succeeded in turning polymers 2 and 3 from weak luminophors into strong emitters by external stimuli of aggregation and cooling. The silolylacetylene monomers HCequivalent toCPS (10), HCequivalent toC(CH2)(9)OPS (11), and C(6)H(5)Cequivalent toC(CH2)(9)OPS (12) were polymerized by NbCl5- and WCl6-Ph4Sn catalysts, which gave high molecular weight polymers in high yields (M-w up to similar to70 x 10(3) Da and yield up to similar to80%). The structures and properties of the polymers were characterized and evaluated by IR, UV, NMR, DSC, TGA, PL, EL, and nanoparticle size analyses. The polymers were thermally stable and lost little weights when heated to similar to350 degreesC. Whereas all the polymers were practically nonluminescent when molecularly dissolved, polymers 2 and 3 became emissive when aggregated in poor solvents or when cooled to low temperatures. Restricted intramolecular rotation or twisting of the silole chromophores in the solid nanoaggregates or at the low temperatures may be responsible for the aggregation- or cooling-induced emission. A multilayer electrolumineseence device using 3 as an active layer emitted a blue light of 496 nm with maximum brightness, current efficiency, and external quantum yield of 1118 cd/m(2), 1.45 cd/A, and 0.55%, respectively.
• Synthesis of Annulated <i>γ</i>-Carbolines and Heteropolycycles by the Palladium-Catalyzed Intramolecular Annulation of Alkynes
  作者：Haiming Zhang、Richard C. Larock

  DOI：10.1021/jo0343228

  日期：2003.6.1

  A variety of N-substituted 2-bromo-1H-indole-3-carboxaldehydes incorporating an alkyne-containing tether on the indole nitrogen have been converted to the corresponding tert-butylimines, which have been subjected to palladium-catalyzed intramolecular iminoannulation, affording various gamma-carboline derivatives with an additional ring fused across the 4- and 5-positions in good to excellent yields. When the tethered carbon-carbon triple bond is terminal or substituted with a triethylsilyl group, the iminoannulation generates a tert-butyl-gamma-carbolinium salt as the major product. The palladium-catalyzed intramolecular annulations of N-substituted 2-bromo-1H-indole-3-carboxaldehyde, methyl 2-iodo-1H-indole-3-carboxylate, and 2-iodo-3-phenyl-1H-indole containing a phenylpentynyl tether produce the corresponding heteropolycycles in moderate to good yields.