1,4-bis[(9-methyl-9H-fluoren-9-yl)methyl]benzene | 852534-08-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 1,4-bis[(9-methyl-9H-fluoren-9-yl)methyl]benzene
• 英文别名: 9-Methyl-9-[[4-[(9-methylfluoren-9-yl)methyl]phenyl]methyl]fluorene；9-methyl-9-[[4-[(9-methylfluoren-9-yl)methyl]phenyl]methyl]fluorene
• CAS: 852534-08-8
• 化学式: C₃₆H₃₀
• 分子量: 462.634
• InChiKey: BBWJCMVKYXWRNP-UHFFFAOYSA-N

物化性质

• 沸点：
  625.4±35.0 °C(Predicted)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  1,4-bis[(9-methyl-9H-fluoren-9-yl)methyl]benzene 、 [2.2.2]p,p,p-cyclophane silver(1+) 以 氘代氯仿 为溶剂， 以99%的产率得到[((CH3)C13H8CH2C6H4CH2C13H8(CH3))Ag](trifluoromethanesulfonate)
  参考文献：
  名称：

  A Versatile and Conformationally Adaptable Fluorene-Based Receptor for Efficient Binding of Silver Cation

  摘要：

  We have designed and synthesized a versatile fluorene-based receptor (1) in a one-pot reaction from readily available precursors, which adapts a deltaphane- or pi-prismand-like conformer via a simple C-C bond rotation. Such a conformational adaptability of 1 allows it to bind a single silver cation with remarkable efficiency (K approximately 15 000 M-1) as monitored by 1H NMR or UV-vis spectroscopy and further confirmed by competition experiments with tris[2.2.2]paracyclophane (or pi-prismand 2) as well as a model compound 3 containing only one fluoranyl ring.

  DOI：

  10.1021/ja051935o
• 作为产物：
  描述：

  芴 、 1,4-对二氯苄 、 碘甲烷 以96%的产率得到1,4-bis[(9-methyl-9H-fluoren-9-yl)methyl]benzene
  参考文献：
  名称：

  A Versatile and Conformationally Adaptable Fluorene-Based Receptor for Efficient Binding of Silver Cation

  摘要：

  We have designed and synthesized a versatile fluorene-based receptor (1) in a one-pot reaction from readily available precursors, which adapts a deltaphane- or pi-prismand-like conformer via a simple C-C bond rotation. Such a conformational adaptability of 1 allows it to bind a single silver cation with remarkable efficiency (K approximately 15 000 M-1) as monitored by 1H NMR or UV-vis spectroscopy and further confirmed by competition experiments with tris[2.2.2]paracyclophane (or pi-prismand 2) as well as a model compound 3 containing only one fluoranyl ring.

  DOI：

  10.1021/ja051935o

文献信息

• Convergent Synthesis of Alternating Fluorene-<i>p</i>-xylene Oligomers and Delineation of the (Silver) Cation-Induced Folding
  作者：Vincent J. Chebny、Rajendra Rathore

  DOI：10.1021/ja0687522

  日期：2007.7.1

  Convergent synthetic routes for the preparation of hitherto unknown fluorene-p-xylene oligomers (containing up to 10 fluorene moieties) from readily available starting materials are described. The conformationally adaptable monomeric receptor (which is made of a pair of fluorene and one p-xylene ring, i.e., Z1 undergoes a simple C-C bond rotation in the presence of silver cations to produce a pi-prismand-like receptor which binds a single silver cation with remarkable efficiency (i.e., K approximate to 15 000 M-1). The data on H-1 NMR spectroscopic titrations with Ag+ together with the density functional theory and AM1 calculations allows us to establish that various oligomers of Z1(i. e... Z2-Z9) also undergo ready folding into the structures that contain multiple pi-prismand-like receptor sites in the presence of silver cations. The multiple cavities in Z3-Z9 accommodate a single silver cation per cavity with efficiency similar to that of Z1.