1-(3-bromopropoxy)adamantane | 359827-33-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-bromopropoxy)adamantane
• CAS: 359827-33-1
• 化学式: C₁₃H₂₁BrO
• 分子量: 273.213
• InChiKey: QLKYIDWWDMZNRC-UHFFFAOYSA-N

物化性质

• 沸点：
  304.6±15.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-(3-bromopropoxy)adamantane 在 N-溴代丁二酰亚胺(NBS) 、 18-冠醚-6 、 potassium carbonate 、 一水合肼 、 三苯基膦 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 4.0h， 生成 [3,5-Bis[3-(1-adamantyloxy)propoxy]phenyl]methanamine
  参考文献：
  名称：

  Water-Soluble Adamantane-Terminated Dendrimers Possessing a Rhenium Core

  摘要：

  A novel type of radiometal-containing dendrimer with potential radiotherapeutical applications is described. Different generations of this adamantane-terminated, Frechet-type dendrimer (28, 29, 30), each consisting of two dendritic wedge ligands around a rhenium core, have been synthesized in organic solvent via reaction with ReO(PPh3)(2)Cl-3. Through complexation of their adamantane groups by beta -cyclodextrins (beta -CDs), these dendrimers were made water soluble (9.6, 0.4, and 0.2 mM, respectively). beta -CD-induced solubilization of the wedges in water allowed the complexes to be made under aqueous conditions, via reaction with rhenium gluconate. Not only does this strategy enable the facile synthesis of the radioactive analogue, the yields for these complex-formation reactions in water also turned out to be far higher than those observed for the reactions in organic solvents.

  DOI：

  10.1021/jo0102718
• 作为产物：
  描述：

  3-(adamantane-1-yloxy)propan-1-ol 在 三溴化磷 作用下， 以 甲苯 为溶剂， 以55%的产率得到1-(3-bromopropoxy)adamantane
  参考文献：
  名称：

  Water-Soluble Adamantane-Terminated Dendrimers Possessing a Rhenium Core

  摘要：

  A novel type of radiometal-containing dendrimer with potential radiotherapeutical applications is described. Different generations of this adamantane-terminated, Frechet-type dendrimer (28, 29, 30), each consisting of two dendritic wedge ligands around a rhenium core, have been synthesized in organic solvent via reaction with ReO(PPh3)(2)Cl-3. Through complexation of their adamantane groups by beta -cyclodextrins (beta -CDs), these dendrimers were made water soluble (9.6, 0.4, and 0.2 mM, respectively). beta -CD-induced solubilization of the wedges in water allowed the complexes to be made under aqueous conditions, via reaction with rhenium gluconate. Not only does this strategy enable the facile synthesis of the radioactive analogue, the yields for these complex-formation reactions in water also turned out to be far higher than those observed for the reactions in organic solvents.

  DOI：

  10.1021/jo0102718

文献信息

• Photoreversible Transformation between Seconds and Hours Time-Scales: Threading of Pillar[5]arene onto the Azobenzene-End of a Viologen Derivative
  作者：Tomoki Ogoshi、Daiki Yamafuji、Takamichi Aoki、Tada-aki Yamagishi

  DOI：10.1021/jo202040p

  日期：2011.11.18

  Photoswitching of the transformation between seconds and hours time-scales is demonstrated using the threading of per-hydroxylated pillar[5]arene onto the azobenzene-end of a viologen derivative. When the azobenzene moiety was in the trans form, the threading of per-hydroxylated pillar[5]arene quickly took place at 25 degrees C and could not be monitored directly. The exchange rate (k) and half-life time (t(1/2)) examined by 2D EXSY NMR spectroscopy were found to be 0.209 +/- 0.013 s(-1) and 3.33 +/- 0.21 s, respectively. In contrast, the cis form of the azobenzene moiety required very long time (k = 2.14 +/- 0.27 x 10(-5) s(-1), t(1/2) = 9.13 +/- 1.2 h) to thread per-hydroxylated pillar[5]arene at 25 degrees C. Photoisomerization from the trans to the cis form generated the following increment of free energy of activation at 25 degrees C: Delta G(in)double dagger (cis form) - Delta G(in)double dagger(trans form) = 22.8 +/- 0.24 kJ mol(-1), which led to the time-scale transformation. The tuning of the threading was also accomplished by heating/cooling: the rate constants increased on heating and decreased on cooling.