2-[2-(3-Ethynylphenyl)ethynyl]-1-[2-[2-(3-ethynylphenyl)ethynyl]naphthalen-1-yl]naphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[2-(3-Ethynylphenyl)ethynyl]-1-[2-[2-(3-ethynylphenyl)ethynyl]naphthalen-1-yl]naphthalene
• 英文别名: 2-[2-(3-ethynylphenyl)ethynyl]-1-[2-[2-(3-ethynylphenyl)ethynyl]naphthalen-1-yl]naphthalene
• 化学式: C₄₀H₂₂
• 分子量: 502.615
• InChiKey: PGLHECOLNXQIGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 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-[2-(3-Ethynylphenyl)ethynyl]-1-[2-[2-(3-ethynylphenyl)ethynyl]naphthalen-1-yl]naphthalene 在 四(三苯基膦)钯 copper(l) iodide 、 二异丙胺 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 Pentadecacyclo[81.3.1.126,30.133,37.140,44.169,73.176,80.04,13.07,12.014,23.015,20.047,56.050,55.057,66.058,63]dononaconta-1(86),4(13),5,7,9,11,14(23),15,17,19,21,26,28,30(92),33(91),34,36,40(90),41,43,47(56),48,50,52,54,57(66),58,60,62,64,69,71,73(89),76,78,80(88),83(87),84-octatriacontaen-2,24,31,38,45,67,74,81-octayne
  参考文献：
  名称：

  Sulfoximine Version of Double Elimination Protocol for Synthesis of Chiral Acetylenic Cyclophanes

  摘要：

  A new strategy for constructing enantiopure acetylenic cyclophanes is described on the basis of one-pot double elimination reaction starting from dialdehydes and bis(sulfoximine)s. In this case, the conventional sulfone protocol affords poorer yields of the desired cyclophanes. Thus, arylene-ethynylene moieties with terminal sulfoximine or formyl functions are linked to binaphthyl cores and these building blocks are then subjected to double elimination reaction. The desired macrocycles are obtained in up to 35% yield. The corresponding Sonogashira coupling fails to afford cyclophanes indicative of effectiveness of the double elimination methodology.

  DOI：

  10.1002/1521-3765(20020503)8:9<2005::aid-chem2005>3.0.co;2-i
• 作为产物：
  描述：

  3,3-diethyl-1-(3-iodophenyl)triaz-1-ene 在 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 、 二异丙胺 、 碘甲烷 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 40.0h， 生成 2-[2-(3-Ethynylphenyl)ethynyl]-1-[2-[2-(3-ethynylphenyl)ethynyl]naphthalen-1-yl]naphthalene
  参考文献：
  名称：

  Sulfoximine Version of Double Elimination Protocol for Synthesis of Chiral Acetylenic Cyclophanes

  摘要：

  A new strategy for constructing enantiopure acetylenic cyclophanes is described on the basis of one-pot double elimination reaction starting from dialdehydes and bis(sulfoximine)s. In this case, the conventional sulfone protocol affords poorer yields of the desired cyclophanes. Thus, arylene-ethynylene moieties with terminal sulfoximine or formyl functions are linked to binaphthyl cores and these building blocks are then subjected to double elimination reaction. The desired macrocycles are obtained in up to 35% yield. The corresponding Sonogashira coupling fails to afford cyclophanes indicative of effectiveness of the double elimination methodology.

  DOI：

  10.1002/1521-3765(20020503)8:9<2005::aid-chem2005>3.0.co;2-i

文献信息

• Metal-Assisted Assembly of Pyridine-Containing Arylene Ethynylene Strands to Enantiopure Double Helicates
  作者：Akihiro Orita、Takehiro Nakano、De Lie An、Kazumi Tanikawa、Kan Wakamatsu、Junzo Otera

  DOI：10.1021/ja048327d

  日期：2004.8.1

  Pyridine-containing arylene ethynylene strands were connected to the 2- and 2'-positions of (R)- and (S)-1,1'-binaphthyl templates. The arylene ethynylene moieties underwent intramolecular coordination with Ag(I) or Cu(I) ion to afford enantiopure double helicates. The double-helical structure was elucidated on the basis of circular dichroic (CD) spectra. The importance of intramolecular complexation of the double strands for the helicate formation was confirmed by comparison with a ligand bearing a single strand. Connection of the strands through an ether linkage enabled a sorting out of the Cotton effect induced by double-helical arylene ethynylene moieties. The CD exciton chirality method unambiguously proved that the termini of the strands approach each other upon complexation and that the sense of the induced helicity is the same as predicted by molecular modeling.