2-(3,3-dimethylbut-1-yn-1-yl)naphthalene | 1391145-01-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(3,3-dimethylbut-1-yn-1-yl)naphthalene
• 英文别名: 2-(3,3-Dimethylbut-1-ynyl)naphthalene
• CAS: 1391145-01-9
• 化学式: C₁₆H₁₆
• 分子量: 208.303
• InChiKey: FHUZRIODCZPGRX-UHFFFAOYSA-N

物化性质

• 沸点：
  332.5±11.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-(3,3-dimethylbut-1-yn-1-yl)naphthalene 在 乙醇 、 potassium tert-butylate 、 1,3-双(2,4,6-三甲基苯基)氯化咪唑 、 联硼酸频那醇酯 、 copper(l) chloride 作用下， 反应 5.0h， 以62%的产率得到cis-2-(3,3-dimethyl-1-butenyl)naphthalene
  参考文献：
  名称：

  Diboron-Assisted Copper-Catalyzed Z-Selective Semihydrogenation of Alkynes Using Ethanol as a Hydrogen Donor

  摘要：

  We herein describe a B(2)Pin(2)-assisted copper-catalyzed semihydrogenation of alkynes. A variety of alkenes were obtained in good to excellent yields with Z-selectivity under mild reaction conditions. Mechanistic studies indicated that a transfer hydrogenation process was involved and ethanol acted as both a solvent and a hydrogen donor in this reaction. The present protocol enabled convenient synthesis of deuterium-substituted Z-alkenes such as Z-Combretastain A4-d(2) in a high deuteration ratio by using readily available ethanol-d(1) as the deuterium source.

  DOI：

  10.1021/acs.joc.9b00321
• 作为产物：
  描述：

  2-乙基萘 在 N-溴代丁二酰亚胺(NBS) 、 2,4,5,6-四(9H-咔唑-9-基)异酞腈 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 24.0h， 生成 2-(3,3-dimethylbut-1-yn-1-yl)naphthalene
  参考文献：
  名称：

  可见光介导的无应变酮的脱酰化炔基化

  摘要：

  首次报道了在蓝光照射下由有机光催化剂催化的未应变酮的解构炔基化。具有多达 63 个实例的广泛底物范围、出色的官能团耐受性和克级反应证明了这种新型炔基化方法的实用性。三氟苯乙酮的二氢喹唑啉酮衍生物在与各种炔基溴化物的三氟甲基化反应中表现良好，已被证明具有作为新型三氟甲基化试剂的潜力。

  DOI：

  10.1021/acs.orglett.3c00145

文献信息

• Emission and transient absorption measurements of substitution effects of C–C triple bonds on relaxation processes of the fluorescent state of naphthalenes
  作者：Minoru Yamaji、Hajime Maeda、Keita Minamida、Tomohiro Maeda、Kengo Asai、Gen-Ichi Konishi、Kazuhiko Mizuno

  DOI：10.1007/s11164-012-0652-4

  日期：2013.1

  Photophysical and photochemical properties of naphthalenes substituted with trimethylsilylethynyl, tert-butylethynyl, and trimethylsilylbutadiynyl groups were investigated by measurement of fluorescence yields, lifetimes, and triplet absorption. Introducing trimethylsilylethynyl and tert-butylethynyl groups to the 1-position of the naphthalene skeleton substantially enhanced fluorescence and intersystem crossing (ISC). The rates of fluorescence of 2-substituted naphthalenes were low. The effect of ethynyl groups on the 1-substituted naphthalenes was rationalized in terms of an increase of the transition moment along the short axis of the naphthalene skeleton. Substitution of the trimethylsilylbutadiynyl group at the 1 or 2-position of the naphthalene skeleton caused a considerable decrease in the fluorescence yield (approximately 0.01) and an increase in the ISC yield (0.99).

  用三甲基硅基乙炔、叔丁基乙炔和三甲基硅基丁二炔基取代的萘的光物理和光化学性质通过测量荧光产率、寿命和三重态吸收进行研究。在萘骨架的1位引入三甲基硅基乙炔和叔丁基乙炔基团显著增强了荧光和内部转换（ISC）。2位取代的萘的荧光速率较低。乙炔基团对1位取代萘的影响可以通过萘骨架短轴上的跃迁矩增加来解释。在萘骨架的1位或2位替代三甲基硅基丁二炔基团导致荧光产率显著降低（约为0.01），而ISC产率增加（0.99）。
• Stoichiometric and Catalytic Lithium Nickelate-Mediated C–F Bond Alkynylation of Fluoroarenes
  作者：Andryj M. Borys、Luca Vedani、Eva Hevia

  DOI：10.1021/jacs.4c02606

  日期：2024.4.10

  cross-coupling reactions under mild conditions. Expanding the synthetic potential of these heterobimetallic complexes, herein we report the success of trilithium nickelate Li3(TMEDA)3Ni(C≡C–Ph)3 in promoting stoichiometric C–F activation of assorted aryl fluorides furnishing novel mixed Li/Ni(0) or Li/Ni(II) species depending on the substrate and conditions employed. These stoichiometric successes can

  低价镍酸盐最近被证明是在温和条件下促进具有挑战性的交叉偶联反应的关键中间体。为了扩大这些异双金属配合物的合成潜力，本文报道了镍酸三锂 Li 3 (TMEDA) 3 Ni(C≡C–Ph) 3成功促进了各种芳基氟化物的化学计量 C–F 活化，从而提供了新型混合 Li/Ni( 0) 或 Li/Ni(II) 物质，具体取决于所用的基材和条件。这些化学计量的成功可以升级到催化方案，以实现芳基氟化物和多氟芳烃与乙炔锂和预催化剂 Ni(COD) 2的原子效率炔基化，无需外部配体、Cu 助催化剂或添加剂的干预。
• Nickel-Catalyzed Alkynylation of Anisoles via C–O Bond Cleavage
  作者：Mamoru Tobisu、Tsuyoshi Takahira、Akimichi Ohtsuki、Naoto Chatani

  DOI：10.1021/ol503707m

  日期：2015.2.6

  A new cross-coupling reaction has been developed for the introduction of an alkyne moiety to an anisole derivative through C-O bond activation using an NHC ligand. This method has been used for direct alkynylation of a broad range of anisole derivatives and provided rapid access to compounds with potential applications in biological and materials science.
• Diboron-Assisted Copper-Catalyzed <i>Z</i>-Selective Semihydrogenation of Alkynes Using Ethanol as a Hydrogen Donor
  作者：Hanyang Bao、Bingwei Zhou、Hongwei Jin、Yunkui Liu

  DOI：10.1021/acs.joc.9b00321

  日期：2019.3.15

  We herein describe a B(2)Pin(2)-assisted copper-catalyzed semihydrogenation of alkynes. A variety of alkenes were obtained in good to excellent yields with Z-selectivity under mild reaction conditions. Mechanistic studies indicated that a transfer hydrogenation process was involved and ethanol acted as both a solvent and a hydrogen donor in this reaction. The present protocol enabled convenient synthesis of deuterium-substituted Z-alkenes such as Z-Combretastain A4-d(2) in a high deuteration ratio by using readily available ethanol-d(1) as the deuterium source.
• Visible-Light-Mediated Deacylated Alkynylation of Unstrained Ketone
  作者：Hao Wu、Shuguang Chen、Dengmengfei Xiao、Feng Li、Kaiyuan Zhou、Xiaocui Yin、Chunni Liu、Xinwei He、Yongjia Shang

  DOI：10.1021/acs.orglett.3c00145

  日期：2023.2.24

  Deconstructive alkynylation of an unstrained ketone catalyzed by an organic photocatalyst under blue light irradiation is reported for the first time. A broad substrate scope with up to 63 examples, excellent functional group tolerance, and gram scale reaction demonstrated the practicality of this novel alkynylation method. The dihydroquinazolinone derivative of trifluoroacetophenone had been proved

  首次报道了在蓝光照射下由有机光催化剂催化的未应变酮的解构炔基化。具有多达 63 个实例的广泛底物范围、出色的官能团耐受性和克级反应证明了这种新型炔基化方法的实用性。三氟苯乙酮的二氢喹唑啉酮衍生物在与各种炔基溴化物的三氟甲基化反应中表现良好，已被证明具有作为新型三氟甲基化试剂的潜力。