10,10,10-Triphenyl-3,6,9-trioxadecyl-p-toluenesulfonate | 133699-10-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 10,10,10-Triphenyl-3,6,9-trioxadecyl-p-toluenesulfonate
• 英文别名: 10,10,10-triphenyl-3,6,9-trioxadecyl p-toluenesulfonate；2-[2-(2-Trityloxyethoxy)ethoxy]ethyl 4-methylbenzenesulfonate
• CAS: 133699-10-2
• 化学式: C₃₂H₃₄O₆S
• 分子量: 546.684
• InChiKey: NIWDCFHIXSXLHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  10,10,10-Triphenyl-3,6,9-trioxadecyl-p-toluenesulfonate 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 乙醇 为溶剂， 85.0 ℃ 、101.33 kPa 条件下， 反应 96.0h， 生成
  参考文献：
  名称：

  Recognition by new symmetrically substituted chiral diphenyl- and di-tert-butylpyridino-18-crown-6 and asymmetrically substituted chiral dimethylpyridino-18-crown-6 ligands of the enantiomers of various organic ammonium perchlorates

  摘要：

  Three new chiral pyridino-18-crown-6 ligands have been prepared. These ligands contain either two phenyl, two tert-butyl, or two methyl substituents on chiral macroring carbon atoms. The chiral di-tert-butyl-substituted diester crown analogue was also prepared. The starting chiral di-tert-butyl-substituted tetraethylene glycol needed to prepare the two di-tert-butyl-substituted crowns was obtained from chiral tert-butyl-1,2-ethanediol, which was resolved from its bis(hydrogen phthalate) brucine salt. A high degree of chiral recognition in CD2Cl2 of the enantiomers of [alpha-(1-naphthyl)ethyl]ammonium perchlorate (NapEt) was shown by the diphenyl- and di-tert-butyl-substituted crowns as measured by differences in the free energy of activation (DELTA-G(c) double-ended-dagger) values determined by temperature-dependent H-1 NMR spectroscopy. The diphenyl- and di-tert-butyl-substituted crowns also exhibited high chiral recognition for the enantiomers of NapEt and other chiral organic ammonium salts in methanol and methanol-chloroform mixtures as shown by a large difference in the log K values determined by a direct H-1 NMR technique.

  DOI：

  10.1021/jo00010a028
• 作为产物：
  描述：

  三乙二醇 在 吡啶 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 38.0h， 生成 10,10,10-Triphenyl-3,6,9-trioxadecyl-p-toluenesulfonate
  参考文献：
  名称：

  Synthesis of novel dansyl appended cyclodextrins. Self-inclusion and sensor properties

  摘要：

  本文描述了三种包含丹磺酰基团且与环糊精之间空间臂长度不同的丹磺酰修饰环糊精衍生物的合成。在化合物4中，荧光团直接与环糊精相连。化合物5含有乙基间隔臂，而化合物6含有三甘醇间隔臂。这些化合物设计用于通过荧光光谱法在水中检测中性有机客体分子，如环己醇和金刚烷羧酸。在中性pH下，这些化合物对客体分子均不敏感。对于化合物4，这是因为丹磺酰基团位于环糊精空腔外部。对于化合物5和6，低敏感性是由丹磺酰基团的强自包合作用引起的。降低pH会导致丹磺酰部分的二甲氨基团质子化，使得自包合作用变得不那么有利，从而导致对客体分子的响应显著增强。这一现象允许通过降低或增加溶液的pH来开启或关闭传感器。化合物6能够在pH1下检测到浓度为5×10⁻⁷mol–1 dm³的金刚烷羧酸。

  DOI：

  10.1039/a701142c

文献信息

• 2,2′-Bipyridine Lariat Calixcrowns: A New Class of Encapsulating Ligands Forming Highly Luminescent Eu3+ and Tb3+ Complexes
  作者：Claudia Fischer、Gianluca Sarti、Alessandro Casnati、Barbara Carrettoni、Ilse Manet、Ruud Schuurman、Massimo Guardigli、Nanda Sabbatini、Rocco Ungaro

  DOI：10.1002/(sici)1521-3765(20000317)6:6<1026::aid-chem1026>3.0.co;2-c

  日期：2000.3.17

  A new class of calix[4]arene crown ethers with one or two bipyridines appended to the polyether ring (lariat calixcrowns) have been designed and synthesized; the luminescence properties of their Eu3+ and Tb3- complexes have been studied in acetonitrile. In this solvent, long lifetimes for the metal emitting states and high metal-luminescence intensities obtained upon ligand excitation have been observed in both Eu3+ and Tb3+ complexes The association constants in methanol have been determined for some of the complexes studied.
• Synthesis, Conformation, and Binding Properties of Cyclodextrin Homo- and Heterodimers Connected through Their Secondary Sides
  作者：Fokke Venema、Hubertus F. M. Nelissen、Patrick Berthault、Nicolaos Birlirakis、Alan E. Rowan、Martinus C. Feiters、Roeland J. M. Nolte

  DOI：10.1002/(sici)1521-3765(19981102)4:11<2237::aid-chem2237>3.0.co;2-4

  日期：1998.11.2

  The synthesis of homo- and heterocyclodextrin (CD) dimers, containing two CD moieties that are linked through their secondary sides by aliphatic or 2,2'-bipyridyl spacers is described. In these dimers, the glucose units to which the spacers are linked have been transformed into altrose units. The dimers with an octamethylene spacer show self-complexation of the spacer in one of the CD moieties in aqueous solution, as revealed by H-1 and C-13 NMR spectroscopy. Using high-resolution (600 and 800 MHz) NMR spectroscopy and a variety of 2D NMR techniques, an assignment of nearly all of the H-1 NMR signals of two of the CD dimers was made, affording detailed information about the structure of these compounds in water. The self-inclusion of the spacers leads to lower binding affinities for ditopic guest molecules like p-toluidino-6-naphthalene sulfonate (TNS) derivatives and porphyrins. When a rigid 2,2'-bipyridyl group is used to connect the two CD moieties, self-inclusion of the spacer is not possible. This results in the formation of different complexes with ditopic guest molecules, for example, a 2:2 complex with a porphyrin.The CD heterodimers described in this paper contain an alpha-CD and a beta-CD moiety. These dimers display site-specific binding of guest molecules.
• HETEROBIFUNCTIONAL REAGENTS AND CONJUGATES WITH OXAALKYLENE UNITS FOR AMPHIPHILIC BRIDGE STRUCTURES
  申请人：Kabi Pharmacia AB

  公开号：EP0540612A1

  公开（公告）日：1993-05-12
• [EN] HETEROBIFUNCTIONAL REAGENTS AND CONJUGATES WITH OXAALKYLENE UNITS FOR AMPHIPHILIC BRIDGE STRUCTURES
  申请人：——

  公开号：WO1992001474A1

  公开（公告）日：1992-02-06

  [EN] A conjugate substance (A-B-A'), where A and A' are residues from organic compounds F and F'; at least one of which being a polymer (carrier) and said compounds having properties that are retained in the conjugate and -B- being a bridge that covalently binds A to A'. The bridge -B- comprises the structure -SrRCONHCH2CH2(OCH2CH2)nO(CH2)mCOY- (I); (i) n is often an integer 1-20 that is uniform for bridges linking identically located positions in individual molecules of the substance; (ii) m = 1 or 2; (iii) R = an alkylene group (1-4 carbon atoms) that possibly is substituted with one or more (1-3) hydroxy(OH) groups; (iv) = sulfur in the form of a thioether (r = 1) or disulfide (r = 2), and Sr binding to saturated carbon atoms in both directions; (v) Y is -NH-, -NHNH- or -NHN=CH- that in their left ends bind to CO and in their right ends to saturated carbon atom or to a carbonyl group (only -NHNH-). A bifunctional coupling reagent complying with the formula Z1RCONHCH2CH2(OCH2CH2)nO(CH2)mZ'1 (III); (i) n is an integer, often 1-20; (ii) m is an integer 1 or 2, preferably 1; (iii) Z1 = a SH-reactive electrophile or thiol (SH-) or protected thiol; (iv) R = an alkylene group (1-4 carbon atoms, that possibly is substituted with one or more (1-3) hydroxy(OH) groups; and (v) Z'1 is activated carboxy. A polyether complying with the formula XCH2CH2(OCH2CH2-)nOCH2Y (IV) where n is an integer 2-20, preferably 3-10. X is H2N- or substituted H2N- that is transformable to H2N-, preferably by hydrolysis or reduction. Y is carboxy or a group that is transformable to carboxy.
  [FR] Substance de conjugué (A-B-A'), dans laquelle A et A' sont des restes de composés organiques F et F'; l'un d'eux au moins est un polymère (porteur) et lesdits composés ont des propriétés qui sont conservées dans le conjugué, et -B- est un pont qui lie par covalence A à A'. Le pont -B- comprend la structure -SrRCONHCH2CH2(OCH2CH2)nO(CH2)mCOY- (I); (i) n est souvent un nombre entier compris entre 1 et 20 qui est uniforme pour des ponts effectuant la liaison de position située de manière identique dans des molécules individuelles de la substance; (ii) m est égal à 1 ou 2; (iii) R est un groupe alkylène (1 à 4 atomes de carbone) qui peut être substitué par 1 ou plusieurs (1-3) groupes hydroxy (OH); (iv) = soufre sous la forme d'un thio-éther (r=1) ou bisulfure (r=2), et Sr se liant à des atomes de carbone saturés dans les deux directions; (v) Y représente -NH-, -NHNH- ou -NHN=CH- qui, dans leurs extrémités de gauche se lient à CO et dans leurs extrémités de droite se lient à un atome de carbone saturé ou à un groupe carbonyle (uniquement -NHNH-). Un réactif de couplage bifonctionnel ayant la formule Z1RCONHCH2CH2(OCH2CH2)nO(CH2)mZ'1 (III); (i) n est un nombre entier souvent compris entre 1 et 20; (ii) m est un nombre entier égal à 1 ou 2, de préférence 1; (iii) Z1 est un thiol ou électrophile réagissant à SH (SH-) ou un thiol protégé; (iv) R est un groupe alkylène (1 à 4 atomes de carbone) qui est éventuellement substitué par un ou plusieurs (1-3) groupes hydroxy (OH); et (v) Z'1 est un carboxy octivé. Un polyéther ayant la formule XCH2CH2(OCH2CH2-)nOCH2Y (IV) dans laquelle n est un nombre entier compris entre 2 et 20, de préférence entre 3 et 10. X représente H2N- ou H2N- substitué qui est transformable en H2N-, de préférence par hydrolyse ou réduction. Y représente un carboxy ou un groupe qui est transformable en carboxy.
• Recognition by new symmetrically substituted chiral diphenyl- and di-tert-butylpyridino-18-crown-6 and asymmetrically substituted chiral dimethylpyridino-18-crown-6 ligands of the enantiomers of various organic ammonium perchlorates
  作者：Peter Huszthy、Jerald S. Bradshaw、Cheng Y. Zhu、Reed M. Izatt、Shneior Lifson

  DOI：10.1021/jo00010a028

  日期：1991.5

  Three new chiral pyridino-18-crown-6 ligands have been prepared. These ligands contain either two phenyl, two tert-butyl, or two methyl substituents on chiral macroring carbon atoms. The chiral di-tert-butyl-substituted diester crown analogue was also prepared. The starting chiral di-tert-butyl-substituted tetraethylene glycol needed to prepare the two di-tert-butyl-substituted crowns was obtained from chiral tert-butyl-1,2-ethanediol, which was resolved from its bis(hydrogen phthalate) brucine salt. A high degree of chiral recognition in CD2Cl2 of the enantiomers of [alpha-(1-naphthyl)ethyl]ammonium perchlorate (NapEt) was shown by the diphenyl- and di-tert-butyl-substituted crowns as measured by differences in the free energy of activation (DELTA-G(c) double-ended-dagger) values determined by temperature-dependent H-1 NMR spectroscopy. The diphenyl- and di-tert-butyl-substituted crowns also exhibited high chiral recognition for the enantiomers of NapEt and other chiral organic ammonium salts in methanol and methanol-chloroform mixtures as shown by a large difference in the log K values determined by a direct H-1 NMR technique.