dimethyl 1-adamantylphosphonate | 37516-07-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: dimethyl 1-adamantylphosphonate
• 英文别名: dimethyl adamantylphosphonate；1-adamantyl-phosphonic acid dimethyl ester；1-Adamatylphosphonsaeuremethylester；Adamantan-1-yl-phosphonic acid dimethyl ester；1-dimethoxyphosphoryladamantane
• CAS: 37516-07-7
• 化学式: C₁₂H₂₁O₃P
• 分子量: 244.271
• InChiKey: HKWOTVWKLMJCNW-UHFFFAOYSA-N

物化性质

• 沸点：
  111-112 °C(Press: 5 Torr)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-溴金刚烷 在 aluminum (III) chloride 、 sodium hydride 、 三氯化磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 24.0h， 生成 dimethyl 1-adamantylphosphonate
  参考文献：
  名称：

  Recognition Characteristics of an Adaptive Vesicular Assembly of Amphiphilic Baskets for Selective Detection and Mitigation of Toxic Nerve Agents

  摘要：

  We used isothermal titration calorimetry to investigate the affinity of basket 1 (470 Å(3)) for trapping variously sized and shaped organophosphonates (OPs) 2-12 (137-244 Å(3)) in water at 298.0 K. The encapsulation is, in each case, driven by favorable entropy (TΔS° = 2.9 kcal/mol), while the enthalpic component stays small and in some cases endothermic (ΔH° ≥ -1 kcal/mol). Presumably, a desolvation of basket 1 and OP guests permits the inclusion complexation at room temperature via a "classical" hydrophobic effect. The amphiphilic basket 1 shows a greater affinity (ΔG° ≈ -5 to -6 kcal/mol), both experimentally and computationally, for encapsulating larger organophosphonates whose size and shape correspond to VX-type agents (289 A(3)). Importantly, baskets assemble into a vesicular nanomaterial (DH ≈ 350 nm) that in the presence of neutral OP compounds undergoes a phase transition to give nanoparticles (DH ≈ 250 nm). Upon the addition of an anionic guest to basket 1, however, there was no formation of nanoparticles and the vesicles grew into larger vesicles (DH ≈ 750 nm). The interconversion of the different nanostructures is reversible and, moreover, a function of the organophosphonate present in solution. On the basis of (1)H NMR spectroscopic data, we deduced that neutral guests insert deep into the basket's cavity to change its shape and thereby promote the conversion of vesicles into nanoparticles. On the contrary, the anionic guests reside at the northern portion of the host to slightly affect its shape and geometric properties, thereby resulting in the vesicles merely transforming into larger vesicles.

  DOI：

  10.1021/ja510477q

文献信息

• Petrov, K. A.; Repin, V. N.; Sorokin, V. D., Journal of general chemistry of the USSR, 1992, vol. 62, # 2.1, p. 245 - 247
  作者：Petrov, K. A.、Repin, V. N.、Sorokin, V. D.

  DOI：——

  日期：——
• Duddeck, Helmut; Elgamal, M. Hani A.; Hanna, Atef G., Phosphorus and Sulfur and the Related Elements, 1986, vol. 28, p. 307 - 314
  作者：Duddeck, Helmut、Elgamal, M. Hani A.、Hanna, Atef G.

  DOI：——

  日期：——
• No, B. I.; Zotov, Yu. L.; Petruneva, R. M., Russian Journal of General Chemistry, 1994, vol. 64, # 2.1, p. 204 - 206
  作者：No, B. I.、Zotov, Yu. L.、Petruneva, R. M.

  DOI：——

  日期：——
• No, B. I.; Zotov, Yu. L.; Petruneva, R. M., Journal of general chemistry of the USSR, 1990, vol. 60, # 10, p. 2139
  作者：No, B. I.、Zotov, Yu. L.、Petruneva, R. M.

  DOI：——

  日期：——
• HO, B. I.;ZOTOV, YU. L.;PETRUNEVA, R. M.
  作者：HO, B. I.、ZOTOV, YU. L.、PETRUNEVA, R. M.

  DOI：——

  日期：——