7,15,23-tribromo-2,3,10,11,18,19-hexahomo-3,11,19-trioxacalix[3]arene-25,26,27-triol | 204781-89-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 7,15,23-tribromo-2,3,10,11,18,19-hexahomo-3,11,19-trioxacalix[3]arene-25,26,27-triol
• 英文别名: 7,15,23-Tribromo-3,11,19-trioxatetracyclo[19.3.1.15,9.113,17]heptacosa-1(24),5,7,9(27),13(26),14,16,21(25),22-nonaene-25,26,27-triol
• CAS: 204781-89-5
• 化学式: C₂₄H₂₁Br₃O₆
• 分子量: 645.139
• InChiKey: PVLUFXSOKXMLKN-UHFFFAOYSA-N

物化性质

• 沸点：
  725.6±60.0 °C(Predicted)
• 密度：
  1.731±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  33
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7,15,23-tribromo-2,3,10,11,18,19-hexahomo-3,11,19-trioxacalix[3]arene-25,26,27-triol 在 四(三苯基膦)钯 盐酸 、 sodium hydride 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 甲苯 为溶剂， 反应 5.0h， 生成 7,15,23-Tripyridin-4-yl-3,11,19-trioxatetracyclo[19.3.1.15,9.113,17]heptacosa-1(24),5,7,9(27),13(26),14,16,21(25),22-nonaene-25,26,27-triol
  参考文献：
  名称：

  Suzuki–Miyaura coupling on the three upper rims of hexahomotrioxacalix[3]arenes

  摘要：

  The efficient functionalization of three upper rims based on Suzuki-Miyaura coupling to temporarily lower rim-protected hexahomotrioxacalix[3]arenes was developed. After deprotection of the three protecting groups, the three upper rim-functionalized and lower rim-free hexahomotrioxacalix[3]arenes 5a-5m were synthesized. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.08.073
• 作为产物：
  描述：

  (5-Bromo-3-hydroxymethyl-2-methoxymethoxy-phenyl)-methanol 在 高氯酸 、 水 、 sodium hydride 作用下， 以 氯仿 为溶剂， 反应 14.33h， 生成 7,15,23-tribromo-2,3,10,11,18,19-hexahomo-3,11,19-trioxacalix[3]arene-25,26,27-triol
  参考文献：
  名称：

  Stepwise Construction of Some Hexahomooxacalix[3]arenes and Their Conformations in Solid State

  摘要：

  Hexahomooxacalix[3]arenes 1 bearing different substituents on their upper rim were synthesized from the corresponding Linear trimers 2 by the acid-catalyzed cyclization. The X-ray crystallographic analyses of 1 (R-1 = R-3 = H, R-2 = t-Bu, and R-1 = Et, R-2 = t-Bu, R-3 = i-Pr) revealed that they adopt a cone conformation, owing to an intramolecular hydrogen-bonded network in the solid state.

  DOI：

  10.1021/jo971945a

文献信息

• Formation and characterization of water-soluble hetero capsules derived from multiple ionic interactions
  作者：Takahiro Kusukawa、Chikako Katano、Chizuru Kim

  DOI：10.1016/j.tet.2011.12.015

  日期：2012.2

  hetero-capsules 1·2 resulting from the ionic interactions between positively charged flexible aniline hydrochloride 1 and negatively charged phosphonate 2 having rigid homooxacalix[3]arene units. The formation of the molecular capsules was studied by NOESY, DOSY NMR spectroscopy and ESI-Mass spectrometry. The water solubility of the capsules is improved by the introduction of mono- or triethylene glycol substituents

  现在我们报告水溶性杂胶囊1 · 2的形成和表征，该杂化是由于带正电荷的柔性苯胺盐酸盐1和带负电荷的膦酸酯2之间的离子相互作用而产生的，而该膦酸盐2具有刚性的均草酸[3]芳烃单元。通过NOESY，DOSY NMR光谱和ESI-Mass光谱研究了分子胶囊的形成。通过在基于均草酸[3]亚芳基的膦酸酯单元2中引入单或三甘醇取代基，可以改善胶囊的水溶性。
• New synthetic route to homooxacalix[n]arenes via reductive coupling of diformylphenols
  作者：Naoki Komatsu

  DOI：10.1016/s0040-4039(00)02336-4

  日期：2001.2

  homocoupling of 4-substituted-2,6-diformylphenols with Et3SiH in the presence of Me3SiOTf gave homooxacalix[n]arenes (1n·R, n=3, 4) in moderate yields. Heterocoupling reaction of 4-substituted-2,6-diformylphenols with tris(trimethylsilyl) ether of 4-substituted-2,6-bis(hydroxymethyl)phenols afforded homooxacalix[n]arenes (23·R1·R2·Rm and 24·R1·R2·R1·Rm, m=1, 2) with different substituents in a one-pot fashion

  在Me 3 SiOTf存在下，4-取代的2,6-二甲酰基苯酚与Et 3 SiH的还原均偶联反应以中等收率得到了高恶唑烷[ n ]芳烃（1 n ·R，n = 3，4）。4-取代的2,6-二甲酰基苯酚与4-取代的2,6-双（羟甲基）苯酚的三（三甲基甲硅烷基）醚的异质偶联反应得到高氧杂芳基[ n ]芳烃（2 3 ·R 1 ·R 2 ·R m和2 4 ·R 1 ·R 2 ·R 1 ·R m，m= 1，2）以一锅的方式带有不同的取代基。
• On the prerequisites for the formation of solution complexes from [60]fullerene and calix[n]arenes: A novel allosteric effect between [60]fullerene and metal cations in calix[n]aryl ester complexes
  作者：Atsushi Ikeda、Yoshio Suzuki、Makoto Yoshimura、Seiji Shinkai

  DOI：10.1016/s0040-4020(98)00012-x

  日期：1998.3

  calix[n]arenes which can interact with [60]fullerene in solution we have screened a number of different calix[n]arenes by spectroscopic methods. We eventually discovered such three calix[n]arenes (15·But·H, 16·But·H, and 23·But·H) which could accept [60]fullerene even in solution. They commonly possess a cone conformation and a benzene ring inclination suitable to [60]fullerene inclusion. Furthermore, it was

  为了找到可以与溶液中的[60]富勒烯相互作用的杯芳烃[n]芳烃，我们已经通过光谱法筛选了许多不同的杯芳烃[n]芳烃。我们最终发现了这三种杯芳烃[n]芳烃（1 5 ·Bu t ·H，1 6 ·Bu t ·H和2 3 ·Bu t·H），即使在溶液中也可以接受[60]富勒烯。它们通常具有适合[60]富勒烯夹杂物的圆锥构象和苯环倾斜度。此外，发现在某些特定金属阳离子的存在下，不能与[60]富勒烯相互作用的杯[n]芳基酯衍生物成为优异的[60]富勒烯受体。这归因于金属诱导的构象变化，以预组织圆锥杯[n]芳基酯。这种现象是一种积极的变构现象，这是富勒烯化学的第一个例子。我们相信这些发现将为新的富勒烯-杯[n]芳烃共轭化学打开一扇门。
• Ion Pair-Driven Heterodimeric Capsule Based on Boronate Esterification:  Construction and the Dynamic Behavior
  作者：Kenichi Kataoka、Tony D. James、Yuji Kubo

  DOI：10.1021/ja076792f

  日期：2007.12.1

  interact with 2 in a protic solution, in the presence of Et4NAcO quantitative formation of a heterodimeric capsule via boronate esterification was observed in the NMR, a direct result of anion-induced boronate ester formation and the Et4N+ template. Reversible boronate esterification allowed us to selectively control capsule assembly using pH switching.

  我们描述了离子对驱动的异二聚体胶囊形成 1 和硼酸附加的六高三氧杂杯 [3] 芳烃 2。虽然 1 在质子溶液中不与 2 相互作用，但在 Et4NAcO 存在下异二聚体胶囊的定量形成在 NMR 中观察到通过硼酸酯化，这是阴离子诱导的硼酸酯形成和 Et4N+ 模板的直接结果。可逆硼酸酯化使我们能够使用 pH 值切换来选择性地控制胶囊组装。
• Construction of a Homooxacalix[3]arene-based Dimeric Capsule Cross-linked by a Pd(II)-pyridine Interaction
  作者：Atsushi Ikeda、Makoto Yoshimura、Fumio Tani、Yoshinori Naruta、Seiji Shinkai

  DOI：10.1246/cl.1998.587

  日期：1998.7

  Homooxacalix[3]arenes bearing 4-pyridyl groups at the 7,15,23-positions formed a dimeric complex with Pd(II). Only when the homooxacalix[3]arene was preorganized to a cone conformation, a dimeric molecular capsule with D3h symmetry was yielded. Mass spectral studies established that CD2Cl2 is included in this cavity.

  在 7,15,23 位带有 4-吡啶基的同氧杂杯 [3] 芳烃与 Pd(II) 形成二聚体复合物。只有当高氧杯[3]芳烃被预先组织成锥形构象时，才会产生具有D3h对称性的二聚分子胶囊。质谱研究确定 CD2Cl2 包含在该腔中。