ABii[C11H23,H,Ph] | 618117-08-1

• 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: ABii[C11H23,H,Ph]
• 英文别名: 3,9-Dioxido-3,9-diphenyl-25,29,33,37-tetra(undecyl)-2,4,8,10,14,16,20,22-octaoxa-3,9-diphosphonianonacyclo[21.15.1.124,38.05,36.07,34.011,32.013,30.017,28.019,26]tetraconta-1(38),5,7(34),11(32),12,17(28),18,23(39),24(40),26,30,35-dodecaene；3,9-dioxido-3,9-diphenyl-25,29,33,37-tetra(undecyl)-2,4,8,10,14,16,20,22-octaoxa-3,9-diphosphonianonacyclo[21.15.1.124,38.05,36.07,34.011,32.013,30.017,28.019,26]tetraconta-1(38),5,7(34),11(32),12,17(28),18,23(39),24(40),26,30,35-dodecaene
• CAS: 618117-08-1；618117-07-0；618117-13-8
• 化学式: C₈₆H₁₁₈O₁₀P₂
• 分子量: 1373.82
• InChiKey: CNGVAKOGPPJXSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  31.9
• 重原子数：
  98
• 可旋转键数：
  42
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ABii[C11H23,H,Ph] 、 二乙胺盐酸盐 、 三乙胺盐酸盐 以 甲醇 、 甲苯 、 乙腈 为溶剂， 生成 、
  参考文献：
  名称：

  Hydrogen bonding in phosphonate cavitands: Investigation of host-guest complexes with ammonium salts

  摘要：

  通过质谱方法和理论计算研究了膦酸空穴剂烷基铵配合物中的氢键。烷基铵离子包括伯、仲、叔甲基铵离子和乙基铵离子。通过使用不同的竞争实验、能量分辨 CID、气相 H/D 交换和配体交换反应，以及对复合物进行 ab initio 理论优化，评估了它们与单膦酸空穴剂、四膦酸空穴剂和两种二膦酸空穴剂的络合情况。研究发现，具有两个或更多相邻 P = O 基团的膦酸空穴体对仲烷基铵离子具有选择性，这是因为它们同时形成了两个稳定的氢键。在离子-分子反应（H/D-和配体-交换）中，观察到两个稳定氢键的形成要么减缓反应，要么完全阻止反应。不过，这仅限于在烷基铵离子的氢键供体位点和空穴配体的邻接氢键受体位点之间形成两个氢键的情况。

  DOI：

  10.1016/j.jasms.2009.11.009
• 作为产物：
  描述：

  C₈₆H₁₁₈O₈P₂S₂ 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以90%的产率得到ABii[C11H23,H,Ph]
  参考文献：
  名称：

  固有地，手性磷酸萘基空分子作为天然铵的人工化学和对映选择性受体†

  摘要：

  合成了在其宽边缘具有各种桥联部分的固有手性磷酸萘基空分子。用cavitand 8通过手性HPLC进行光学拆分，得到对映纯化合物（+）- 8和（-）- 8。主体8和12的分子结构通过X射线衍射确定。通过1 H和31 P NMR光谱研究主体性质。磷酸萘基空分子与手性铵神经递质形成包合物，其中一些对右手或左手宿主对映体呈现对映选择性。

  DOI：

  10.1039/c1ob05194f

文献信息

• Restricted Guest Tumbling in Phosphorylated Self-Assembled Capsules
  作者：Steven Harthong、Béatrice Dubessy、Jérôme Vachon、Christophe Aronica、Jean-Christophe Mulatier、Jean-Pierre Dutasta

  DOI：10.1021/ja104388t

  日期：2010.11.10

  ABii diphosphonatocavitands self-assemble in chloroform solution to form dimeric molecular capsules. The molecular capsules can incarcerate an N-methylpyridinium or N-methylpicolinium guest. We have demonstrated that the supramolecular assembly acts as a molecular rotor as a result of the restricted motion of the guest inside the molecular cavity. In the solid state, X-ray diffraction analysis of the free host showed that two cavitands interact through strong hydrogen bonds to give the supramolecular self-assembled capsule. The solid-state structure of the N-methylpicolinium complex is comparable to that of the free host and indicates that the guest is not a prerequisite for the formation of the capsule. DOSY NMR studies provided a definitive argument for the formation of the free and complexed supramolecular capsule in CDCl3 solution. In solution, the tumbling of the N-methylpyridinium and N-methylpicolinium guests about the equatorial axes of the host can be frozen and differs by the respective energy barriers, with the larger picolinium substrate having a larger value (Delta G(double dagger) = 69.7 kJ mol(-1)) than the shorter pyridinium guest (Delta G(double dagger) = 44.8 kJ mol(-1)). This behavior corresponds to the restricted rotation of a rotator in a supramolecular rotor.
• Hydrogen bonding in phosphonate cavitands: Investigation of host-guest complexes with ammonium salts
  作者：Elina Kalenius、Raisa Neitola、Michele Suman、Enrico Dalcanale、Pirjo Vainiotalo

  DOI：10.1016/j.jasms.2009.11.009

  日期：2010.3.1

  The H-bonding in alkylammonium complexes of phosphonate cavitands were studied by mass spectrometric methods and theoretical calculations. The alkylammonium ions included primary, secondary, and tertiary methyl- and ethylammonium ions. Their complexation with mono-, tetra-, and two di-phosphonate cavitands, which differ according to the number and position of H-bond acceptor P = O groups, was evaluated by using different competition experiments, energy-resolved CID, gas-phase H/D-exchange, and ligand-exchange reactions, together with ab initio theoretical optimization of the complexes. The phosphonate cavitands with two or more adjacent P = O groups were found to be selective towards secondary alkylammonium ions, due to simultaneous formation of two stable hydrogen bonds. In the ion-molecule reactions (both H/D- and ligand-exchange), the formation of two stable hydrogen bonds was observed either to slow down the reaction or to completely prevent it. This was, however, limited to situations where two hydrogen bonds are formed between the H-bond donor sites of the alkyl ammonium ion and the vicinal H-bond acceptor sites of the cavitand.

  通过质谱方法和理论计算研究了膦酸空穴剂烷基铵配合物中的氢键。烷基铵离子包括伯、仲、叔甲基铵离子和乙基铵离子。通过使用不同的竞争实验、能量分辨 CID、气相 H/D 交换和配体交换反应，以及对复合物进行 ab initio 理论优化，评估了它们与单膦酸空穴剂、四膦酸空穴剂和两种二膦酸空穴剂的络合情况。研究发现，具有两个或更多相邻 P = O 基团的膦酸空穴体对仲烷基铵离子具有选择性，这是因为它们同时形成了两个稳定的氢键。在离子-分子反应（H/D-和配体-交换）中，观察到两个稳定氢键的形成要么减缓反应，要么完全阻止反应。不过，这仅限于在烷基铵离子的氢键供体位点和空穴配体的邻接氢键受体位点之间形成两个氢键的情况。
• Inherently chiral phosphonatocavitands as artificial chemo- and enantio-selective receptors of natural ammoniums
  作者：Jérôme Vachon、Steven Harthong、Erwann Jeanneau、Christophe Aronica、Nicolas Vanthuyne、Christian Roussel、Jean-Pierre Dutasta

  DOI：10.1039/c1ob05194f

  日期：——

  Inherently chiral phosphonatocavitands with various bridging moieties at their wide rim were synthesized. Optical resolution by chiral HPLC was performed with cavitand 8 to afford enantiopure compounds (+)-8 and (−)-8. The molecular structures of hosts 8 and 12 were determined by X-ray diffraction. The host properties were investigated by 1H and 31P NMR spectroscopy. The phosphonatocavitands form inclusion

  合成了在其宽边缘具有各种桥联部分的固有手性磷酸萘基空分子。用cavitand 8通过手性HPLC进行光学拆分，得到对映纯化合物（+）- 8和（-）- 8。主体8和12的分子结构通过X射线衍射确定。通过1 H和31 P NMR光谱研究主体性质。磷酸萘基空分子与手性铵神经递质形成包合物，其中一些对右手或左手宿主对映体呈现对映选择性。