4-(5-iodo-1-naphthyl)-2-methyl-3-butyn-2-ol | 476181-81-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(5-iodo-1-naphthyl)-2-methyl-3-butyn-2-ol
• 英文别名: 4-(5-iodo-1-naphthyl)-2-methylbut-3-yn-2-ol；4-(5-Iodonaphthalen-1-yl)-2-methylbut-3-yn-2-ol
• CAS: 476181-81-4
• 化学式: C₁₅H₁₃IO
• 分子量: 336.172
• InChiKey: JETHEBVBFXMHLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  4-(5-iodo-1-naphthyl)-2-methyl-3-butyn-2-ol 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 copper(l) iodide 作用下， 以 三乙胺 、 甲苯 为溶剂， 反应 27.0h， 生成 1-ethynyl-5-[(5-nitro-1-naphthyl)ethynyl]naphthalene
  参考文献：
  名称：

  Carbon Networks Based on 1,5-Naphthalene Units. Synthesis of 1,5-Naphthalene Nanostructures with Extended π-Conjugation

  摘要：

  The synthesis and spectroscopic characterization of nanometer-sized conjugated molecules of 5-X-naphthylethynyl (X = NO2, NMe2) units with precise length and constitution have been carried out. A new extended pi-conjugated 5-nitronaphthyl family was synthesized by palladium-catalyzed cross-coupling reaction between the protected 5-iodonaphthylethynyl 5a and 1-ethynyl-5-nitronaphthalene 9, or the resulting ethynyl compound 11 and the 1-iodo-5-nitronaphthalene 3. Catalytic oxidative dimerization of the terminal acetylene compounds permits the isolation of the corresponding 1,3-butadiyne derivatives 16-18, with the nitro groups at the ends of the conjugation, in excellent yields. A new family of conjugated 5-nitro-(naphthylethynyl)-[5-(N,N-dimethylamino)]naphthalene (20-22), was also synthesized by palladium-catalyzed cross-coupling reaction between 5-iodo-N,N-dimethylnaphthalene-1-amine (19) with the appropriate terminal acetylene (9, 11, and 13 respectively). Compounds 20-22 show a fluorescence emission and also exhibit a charge-transfer absorption in the visible spectrum. X-ray structure of 20 confirms a centrosymmetric dimer association with an interplanar distance of 3.43 Angstrom, and the naphthalene rings adopt an anti conformation around the Cequivalent toC triple bond.

  DOI：

  10.1021/jo0203589
• 作为产物：
  描述：

  1,5-二硝基萘 在 bis-triphenylphosphine-palladium(II) chloride sodium sulfide 、 ammonium hydroxide 、 copper(l) iodide 、 硫酸 、 二乙胺 、 potassium iodide 、 sodium nitrite 作用下， 生成 4-(5-iodo-1-naphthyl)-2-methyl-3-butyn-2-ol
  参考文献：
  名称：

  具有扩展的π-共轭的1，5-萘乙炔基纳米结构网络的合成。在相容的CO 2气氛下钯催化有效的异质偶联

  摘要：

  合成的新的扩展的π共轭5- Ñ，Ñ -dimethylaminonaphthyl家庭用保护的5- iodonaphthylethynyl和1-乙炔基-5-（间钯催化的交叉偶联反应进行Ñ，Ñ二甲基氨基）萘。在氩气气氛下，仅分离均一的偶联产物1，4-（N，N-二甲基氨基）萘基-1，3-丁二炔，收率很高。然而，在相容和纯净的二氧化碳气氛下，以优异的产率获得了交叉偶联产物。

  DOI：

  10.1016/s0040-4039(03)00344-7

文献信息

• Carbon dendron nano-chains with π-extended conjugation based on end-capped N,N-dimethylamino in linear 1,4-phenylethynyl or in 1,5-naphthylethynyl subunits: fluorescence analysis
  作者：J. Gonzalo Rodríguez、J. Luis Tejedor

  DOI：10.1016/j.tet.2004.12.054

  日期：2005.2

  Abstract The synthesis of dendrons with the end-capped 5-( N , N -dimethylamino)naphthyl-1-ethynyl unit connected to conjugated naphthylethynyl or p -phenylethynyl chains, as the branches of the 1,3,5-substituted benzene core, have been undertaken by heterocoupling reaction between 1,3,5-triiodobenzene and the convenient end-capped 5-( N , N -dimethylamino)naphthylacetylene or 5-( N , N -dimethyla

  摘要 以 5-( N , N - 二甲基氨基) 萘基-1-乙炔基单元连接到共轭萘乙炔基或对苯乙炔基链，作为 1,3,5-取代苯核心的支链，合成树枝状化合物，在钯-铜催化剂存在下，通过 1,3,5-三碘苯与方便的封端 5-(N,N-二甲氨基)萘乙炔或 5-(N,N-二甲氨基)萘乙炔基苯乙炔之间的杂偶联反应进行系统，产量高。已经分析了交替的萘乙炔基-苯乙炔基链对树突结构中荧光发射辐射的影响。
• Synthesis of carbon dendron nano-chains with π-extended conjugation based on linear 1,4-phenylethynyl and 1,5-naphthylethynyl subunits
  作者：J.Gonzalo Rodrı́guez、J.Luis Tejedor、Jorge Esquivias、Cristina Dı́az

  DOI：10.1016/s0040-4039(03)01615-0

  日期：2003.8

  A convenient and efficient synthesis of 3,5-di(trimethylsilylethynyl)phenylacetylene and p-[3,5-di(trimethylsilylethynyl)-1-phenylethynyl]phenylacetylene and the naphthylethynyl homologues terminal acetylenes of 5-(N,N-dimethylamino)naphthylethyne have been carried out. These terminal acetylene compounds serve to prepare nanometer-sized conjugated 1,3,5-tri(ethynylphenyl)benzene and 1,3,5-tri(ethynylnaphthyl)benzene

  3,5-二（三甲基甲硅烷基乙炔基）苯基乙炔和对-[3,5-二（三甲基甲硅烷基乙炔基）-1-苯基乙炔基]苯基乙炔和5-（N，N-二甲基氨基）萘乙炔的萘乙炔基同系物末端乙炔的简便有效合成已经进行了。这些末端乙炔化合物通过与1,3,5-三碘代苯催化杂化，用于制备纳米级的共轭1,3,5-三（乙炔基苯基）苯和1,3,5-三（乙炔基萘基）苯低聚物。由钯制成，收率极高。乙炔基苯基或乙炔基萘基同系物链均显示出荧光发射辐射，具有重要的量子产率。
• End-Capped, Conjugated (Dimethylamino)naphthyl Nanostructures with Alternating (1-Naphthylethynyl-<i>p</i>-phenylethynyl)_<i>x</i>Branches on a 1,3,5-Substituted Benzene Core
  作者：J. Gonzalo Rodríguez、J. Luis Tejedor

  DOI：10.1002/ejoc.200400529

  日期：2005.1

  Alternating (1-naphthylethynyl-p-phenylethynyl)x 1,3,5-trisubstituted benzene dendrons were efficiently synthesised by the heterocoupling reaction between (1-naphthylethynyl-p-phenyl)xacetylene (x = 1) and 1,3,5-triiodobenzene in the presence of a palladium-copper catalyst system. A longer terminal acetylene chain (x = 2) was obtained from the heterocoupling between 1,3,5-tri(1-ethynyl-5-naphthylethynyl)benzene

  通过（1-萘乙炔基-p-苯基）x乙炔（x = 1）和1,3,5-之间的杂偶联反应有效地合成了交替（1-萘乙炔基-对苯基乙炔基）x 1,3,5-三取代苯树枝状化合物在钯-铜催化剂体系存在下的三碘苯。从 1,3,5-三(1-乙炔基-5-萘乙炔基)苯和适当的碘芳基衍生物之间的杂偶联获得更长的末端乙炔链 (x = 2)。交替链及其树枝状结构显示荧光发射，具有相似的波长和量子产率。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Synthesis of the end-capped 5-(N,N-dimethylamino)naphthyl-1-ethynyl derivatives and their 1,4-di[5-(N,N-dimethylamino)naphthyl]-1,3-butadiynes: anti rotamer structure
  作者：J. Gonzalo Rodríguez、J. Luis Tejedor

  DOI：10.1016/j.tet.2005.01.109

  日期：2005.3

  A new family of the end-capped 5-(N,N-dimethylamino)naphthylethynyl chains were synthesized, as terminal acetylenes or poly(yne) structures, by heterocoupling between 5-iodo-N,N-dimethylnaphthalen-1-amine and 2-methyl-3-butyn-2-ol or 4-(5-iodo-1-naphthyl)-2-methyl-3-butyn-2-ol, catalyzed by the palladium-copper system. Catalytic homocoupling of the terminal acetylenes, affords to 1,4-dinaphthyl-1,3-butadiyne nanostructures. X-ray diffraction analysis of 1,4-di(alpha-naphthyl)-1,3-butadiyne shows that the naphthalene rings are in the anti configuration along the acetylene axis. All the conjugated compounds show an important fluorescent emission radiation. (c) 2005 Elsevier Ltd. All rights reserved.