1,3,5,7-tetrakis(bromoacetoxy)adamantane | 252644-04-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,3,5,7-tetrakis(bromoacetoxy)adamantane
• 英文别名: [3,5,7-Tris[(2-bromoacetyl)oxy]-1-adamantyl] 2-bromoacetate
• CAS: 252644-04-5
• 化学式: C₁₈H₂₀Br₄O₈
• 分子量: 683.968
• InChiKey: CFZFTRKMAFTBPM-UHFFFAOYSA-N

物化性质

• 熔点：
  170.5-171 °C
• 沸点：
  584.4±50.0 °C(predicted)
• 密度：
  2.04±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,3,5,7-tetrakis(bromoacetoxy)adamantane 在 sodium azide 、 水 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 C₁₈H₂₈N₄O₈
  参考文献：
  名称：

  发散和收敛方法合成新型聚酯胺树枝状聚合物

  摘要：

  合成具有金刚烷结构作为核的新型树状聚合物，使得即使低代树状聚合物也具有球状结构。此外，我们尝试通过使用酯键赋予它们可生物降解的功能。树枝状大分子的合成，特别是在更高的世代中，通过逐步的方法证明是困难的，因此使用会聚路线，其中金刚烷核在最后一步中偶联至树枝状链段。直到第三代，我们才通过收敛方法实现了两种不同的树枝状大分子的合成。与发散的树状大分子相比，收敛的树状大分子的合成产率高，并且通过GPC分析发现两种树状大分子均具有窄的多分散性。

  DOI：

  10.1016/j.tet.2013.06.024
• 作为产物：
  描述：

  1,3,5,7-四羟基金刚烷 、 溴乙酰溴 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以82%的产率得到1,3,5,7-tetrakis(bromoacetoxy)adamantane
  参考文献：
  名称：

  Synthesis and Properties of Multiarmed Geminis

  摘要：

  Three families of multiarmed and multicationic gemini surfactants, having pentaerythritol, dipentaerythritol, or adamantane cores, were synthesized and examined for their colloidal properties in water. Geminis with four or six six-carbon chains are highly water-soluble and do not self-assemble. But surface tension and conductivity measurements show that the geminis with four or six eight-carbon chains form micelles in the 3-6 mM range (compared to 0.5 M for a corresponding surfactant with a single chain). According to dynamic light scattering, these micelles are small (<30 Angstrom diameter); no evidence of dendritic growth below 25 mM is evident. Geminis with four or six 12-carbon chains are too water-insoluble to examine for micelle formation. It is concluded the outward projection of the hydrocarbon chains in water greatly enhances the propensity of the surfactants to self-assemble. Micellar growth is seemingly restricted by chain pairing, chain looping, and associative ring formation. Since;the aggregates have, despite these effects, greater residual water-hydrocarbon contact than found in typical micelles, water solubility of surfactants having longer chains is impaired.

  DOI：

  10.1021/jo9912350

文献信息

• Synthesis and Properties of Multiarmed Geminis
  作者：Fredric M. Menger、Vasily A. Migulin

  DOI：10.1021/jo9912350

  日期：1999.11.1

  Three families of multiarmed and multicationic gemini surfactants, having pentaerythritol, dipentaerythritol, or adamantane cores, were synthesized and examined for their colloidal properties in water. Geminis with four or six six-carbon chains are highly water-soluble and do not self-assemble. But surface tension and conductivity measurements show that the geminis with four or six eight-carbon chains form micelles in the 3-6 mM range (compared to 0.5 M for a corresponding surfactant with a single chain). According to dynamic light scattering, these micelles are small (<30 Angstrom diameter); no evidence of dendritic growth below 25 mM is evident. Geminis with four or six 12-carbon chains are too water-insoluble to examine for micelle formation. It is concluded the outward projection of the hydrocarbon chains in water greatly enhances the propensity of the surfactants to self-assemble. Micellar growth is seemingly restricted by chain pairing, chain looping, and associative ring formation. Since;the aggregates have, despite these effects, greater residual water-hydrocarbon contact than found in typical micelles, water solubility of surfactants having longer chains is impaired.
• Synthesis of novel polyesteramine dendrimers by divergent and convergent methods
  作者：Hitoshi Akiyama、Kazuyuki Miyashita、Yoshiyuki Hari、Satoshi Obika、Takeshi Imanishi

  DOI：10.1016/j.tet.2013.06.024

  日期：2013.8

  Novel dendrimers having an adamantane structure as a core were synthesized such that even low generation dendrimers had a globular structure. Moreover we tried to give them biodegradable function by using ester bonds. Synthesis of the dendrimers, particularly at higher generations, proved difficult via a stepwise procedure, and thus a convergent route was used in which the adamantane core is coupled

  合成具有金刚烷结构作为核的新型树状聚合物，使得即使低代树状聚合物也具有球状结构。此外，我们尝试通过使用酯键赋予它们可生物降解的功能。树枝状大分子的合成，特别是在更高的世代中，通过逐步的方法证明是困难的，因此使用会聚路线，其中金刚烷核在最后一步中偶联至树枝状链段。直到第三代，我们才通过收敛方法实现了两种不同的树枝状大分子的合成。与发散的树状大分子相比，收敛的树状大分子的合成产率高，并且通过GPC分析发现两种树状大分子均具有窄的多分散性。