2,2'-bis(acetyl)-6,6'-bis(ethynyl)-1,1'-binaphthalene | 533910-09-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2'-bis(acetyl)-6,6'-bis(ethynyl)-1,1'-binaphthalene
• 英文别名: (R)-2,2'-diacetoxy-6,6'-diethynyl-1,1'-binaphthalene；(R)-2,2'-diacetoxy-1,1'-binaphthyl-6,6'-bis(ethyne)；[1-(2-Acetyloxy-6-ethynylnaphthalen-1-yl)-6-ethynylnaphthalen-2-yl] acetate
• CAS: 533910-09-7
• 化学式: C₂₈H₁₈O₄
• 分子量: 418.449
• InChiKey: RXKAATHCQUNNQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  顺-二氯双(三乙基膦)铂(II) 、 2,2'-bis(acetyl)-6,6'-bis(ethynyl)-1,1'-binaphthalene 在 copper(l) chloride 作用下， 以 further solvent(s) 为溶剂， 以59%的产率得到cis-[(2,2'-bis(acetyl)-6,6'-bis(ethynyl)-1,1'-binaphthalene)bis(triethylphosphine)platinum(II)]2
  参考文献：
  名称：

  A chiral metallacyclophane for asymmetric catalysisElectonic supplementary information (ESI) available: experimental details and analytical data for 2 and 3, and general procedure for analysis. See http://www.rsc.org/suppdata/cc/b2/b208324h/

  摘要：

  手性金属环烯烃是由顺式-(PEt3)2PtCl2和对映纯的对称的1,1′-联萘-6,6′-双(炔烃)自组装而成，并用于对醛的高对映选择性催化二乙基锌加成，生成手性二级醇。

  DOI：

  10.1039/b208324h

文献信息

• Directed Assembly of Mesoscopic Metallocycles with Controllable Size, Chirality, and Functionality Based on the Robust Pt−Alkynyl Linkage
  作者：Hua Jiang、Wenbin Lin

  DOI：10.1021/ja0633013

  日期：2006.8.1

  and 31) and [Pt](n)()L(n)()(+1)H(2) (n = 1, 2, 3, 4, 5, 6, 10, 18, and 30), and have been characterized by a variety of techniques, including (1)H(31)P}, (13)C(1)H}, and (31)P(1)H} NMR spectroscopy, MALDI-TOF MS, elemental analysis, FT-IR, UV-vis, CD, size-exclusion chromatography, and diffusion-ordered NMR spectroscopy. The present synthetic methodology was also extended to the synthesis of non-homochiral

  本文描述了具有多达 38 个 6,6'-双(炔基)-1,1'-联萘桥连配体 (L) 和 38 个反式-Pt(PEt(3))(2) 的大型同手性金属环的快速逐步定向组装([Pt]) 中心和直径高达 22 nm 的空腔。这些前所未有的介观金属环是通过不同长度的低聚结构单元 L(m)()[Pt](m)()(+1)Cl(2) (m = 1, 2, 3, 5, 7 , 11, 19, 和 31) 和 [Pt](n)()L(n)()(+1)H(2) (n = 1, 2, 3, 4, 5, 6, 10, 18,和 30)，并已通过多种技术进行表征，包括 (1)H(31)P}、(13)C(1)H} 和 (31)P(1)H} NMR 光谱、MALDI-TOF MS、元素分析、FT-IR、UV-vis、CD、尺寸排阻色谱和扩散有序核磁共振光谱。本合成方法还扩展到具有非常不同的拓扑结构和大环结构的非同手性
• Self-Assembly of Chiral Molecular Polygons
  作者：Hua Jiang、Wenbin Lin

  DOI：10.1021/ja034402t

  日期：2003.7.1

  Treatment of 2,2'-diacetyl-1,1'-binaphthyl-6,6'-bis(ethyne), L-H2, with 1 equiv of trans-Pt(PEt3)2Cl2 led to a mixture of different sizes of chiral metallocycles [trans-(PEt3)2Pt(L)]n (n = 3-8, 1-6). Each of the chiral molecular polygons 1-6 was purified by silica gel column chromatography and characterized by 1H, 13C1H}, and 31P1H} NMR spectroscopy, MS, IR, UV-vis, and circular dichroism spectroscopies, and microanalysis. The presence of tunable cavities (1.4-4.3 nm) and chiral functionalities in these molecular polygons promises to make them excellent receptors for a variety of guests.
• Chiral molecular polygons based on the Pt-alkynyl linkage: Self-assembly, characterization, and functionalization
  作者：Hua Jiang、Wenbin Lin

  DOI：10.1016/j.jorganchem.2005.03.049

  日期：2005.11

  Treatment of 2,2'-diacetoxy- 1, 1'-binaphthyl-6,6'-bis(ethyne), L-H-2 with one equiv of trans-Pt(PEt3)(2)Cl-2 led to a mixture of different sizes of chiral metallocycles [trans-(PEt3)(2)Pt(L)](n) (n = 3-8, 1-6). Each of the chiral molecular polygons 1-6 was purified by silica-gel column chromatography and characterized by H-1, C-13H-1}, and P-31H-1} NMR spectroscopy, MS, IR, UV-Vis, and circular dichroism (CD) spectroscopies, size exclusion chromatography, and microanalysis. Chiral molecular square 2 was also characterized by single-crystal X-ray diffraction. The acetyl groups of 2 were readily deprotected under mild conditions to generate 2a which possesses exposed chiral dihydroxy functional groups. The dihydroxy groups were functionalized with n-octadecyl chains or Frechet-type dendrons to generate dendritic molecules built on a chiral molecular square core. This work shows the potential of generating interesting functional supramolecular systems based oil Pt-alkynyl chiral molecular polygons. (c) 2005 Published by Elsevier B.V.