5-iodo-N,N-dimethylnaphthalene-1-amine | 476181-94-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-iodo-N,N-dimethylnaphthalene-1-amine
• 英文别名: 5-iodo-N,N-dimethylnaphthalen-1-amine
• CAS: 476181-94-9
• 化学式: C₁₂H₁₂IN
• 分子量: 297.138
• InChiKey: FOTCCNBUXRWDJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-iodo-N,N-dimethylnaphthalene-1-amine 在 bis-triphenylphosphine-palladium(II) chloride sodium hydroxide 、 copper (I) iodide 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 25.0h， 生成 1-ethynyl-5-(N,N-dimethylamino)naphthalene
  参考文献：
  名称：

  基于线性 1,4-苯乙炔基或 1,5-萘乙炔基亚基中的封端 N,N-二甲氨基的 π 延伸共轭碳树突纳米链：荧光分析

  摘要：

  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。

  DOI：

  10.1016/j.tet.2004.12.054
• 作为产物：
  描述：

  甲酸 、 5-碘萘-1-胺 在 sodium cyanoborohydride 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 以100%的产率得到5-iodo-N,N-dimethylnaphthalene-1-amine
  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

• Palladium-catalyzed reductive Heck-type vinylative dearomatization of unfunctionalized halonaphthalene derivatives
  作者：Yingchao Dou、Liting Yang、Lu Zhang、Panke Zhang、Heng Li、Guanyu Yang

  DOI：10.1039/c6ra22310a

  日期：——

  A novel strategy for the dearomatization of inactive 1-halonaphthalenes via palladium-catalyzed reductive Heck-type vinylative reaction was successfully developed.

  通过钯催化还原Heck型烯基反应，成功开发了一种新的策略，用于去芳香化不活性的1-卤代萘。
• Design and synthesis of environmentally sensitive fluorescent 2-naphthylethynylated 2′-deoxyadenosines: Detection of target DNA via changes in fluorescence intensity and wavelength
  作者：Azusa Suzuki、Ryota Kozakai、Tatsuya Aso、Isao Saito、Takuya Takeda、Yoshio Saito

  DOI：10.1016/j.bmcl.2015.11.037

  日期：2016.1

  Various C2-naphthylethynylated 2'-deoxyadenosines were synthesized as environmentally sensitive fluorescent (ESF) nucleosides and their photophysical properties were examined. Among the ESF nucleosides synthesized, four exhibited strong solvatochromicity, two of which were incorporated into oligodeoxynucleotides (ODNs). These ODN probes were able to detect target DNA through distinct changes in fluorescence intensity and wavelength and acted as effective reporter probes. (C) 2015 Elsevier Ltd. All rights reserved.
• Carbon Networks Based on 1,5-Naphthalene Units. Synthesis of 1,5-Naphthalene Nanostructures with Extended π-Conjugation
  作者：J. Gonzalo Rodríguez、J. Luis Tejedor

  DOI：10.1021/jo0203589

  日期：2002.11.1

  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.
• 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.