penta(p-tolyl)antimony(V) | 51017-91-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: penta(p-tolyl)antimony(V)
• 英文别名: penta(para-tolyl)antimony；penta(p-tolyl)antimony
• CAS: 51017-91-5
• 化学式: C₃₅H₃₅Sb
• 分子量: 577.413
• InChiKey: GNQXBGQXVGAVEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  五氟苯酚 、 penta(p-tolyl)antimony(V) 以 甲苯 为溶剂， 反应 0.25h， 以96%的产率得到2,3,4,5,6-pentafluorophenoxytetra-p-tolylantimony
  参考文献：
  名称：

  Tetra- and triarylantimony pentafluoroand pentachlorophenoxides: Synthesis and structure

  摘要：

  2,3,4,5,6-Pentafluorophenoxytetraphenylantimony (I), 2,3,4,5,6-pentachlorophenoxytetraphenylantimony ((II)), 2,3,4,5,6-pentafluorophenoxytetra-p-tolylantimony (III), and 2,3,4,5,6-pentachlorophenoxytetra-p-tolylantimony (IV) were synthesized by the reaction of pentaarylantimony (Ar = Ph, p-Tol) with pentafluoro- and pentachlorophenol in toluene. Compounds I-IV were also synthesized with yields of up to 95% from pentaarylantimony and triarylantimony diaroxides. Triarylantimony diaroxides Ph3Sb(OC6F5)(2) (V), Ph3Sb(OC6Cl5)(2) (VI), p-Tol(3)Sb(OC6F5)(2) (VII), p-Tol(3)Sb(OC6Cl5)(2) (VIII) were synthesized from triarylantimony, tert-butylhydroperoxide, and phenol in ether. The Sb atoms in compounds I-VIII had a distorted trigonal bipyramidal coordination with electronegative ligands in axial positions.

  DOI：

  10.1134/s0036023617100163
• 作为试剂：
  描述：

  2,4,6-三叔丁基苯酚 在 penta(p-tolyl)antimony(V) 作用下， 以 水 、 甲苯 为溶剂， 反应 48.0h， 以37%的产率得到2,4,6-tri-tert-butyl-4-hydroxy-2,5-cyclohexadienone
  参考文献：
  名称：

  Sharutin; Sharutina; Osipov, Russian Journal of General Chemistry, 2000, vol. 70, # 8, p. 1254 - 1255

  摘要：

  DOI：

文献信息

• Reaction of pentaarylantimony with acid halide, aldehyde and ketone
  作者：Masahiro Fujiwara、Mutsuo Tanaka、Akio Baba、Hisanori Ando、Yoshie Souma

  DOI：10.1016/0022-328x(95)05793-o

  日期：1996.2

  ntimony) was found to be a mild arylation reagent. The arylation was chemoselective toward aromatic acid halides to give the corresponding aromatic ketones. No direct addition to ketone and acid anhydride occurred. Arylation reactions of aldehyde or ketone were promoted by the addition of Lewis acid. The nucleophilicities of aromatic antimony compounds depend on the number of antimony-aromatic carbon

  发现五芳基锑（五苯基锑，五对甲苯基苯甲酸和五对氯苯基苯锑）是温和的芳基化试剂。芳基化对芳族酰卤具有化学选择性，得到相应的芳族酮。没有直接添加到酮和酸酐中。通过添加路易斯酸来促进醛或酮的丙烯酸化反应。芳族锑化合物的亲核性取决于锑-芳族碳键的数量。
• Tetra(para-Tolyl)antimony aroxides (4-MeC6H4)4SbOAr (Ar = C6H3Cl2-2,6, C6H3(NO2)2-2,4, and C6H2(NO2)3-2,4,6): Syntheses and structures
  作者：V. V. Sharutin、O. K. Sharutina、P. V. Andreev

  DOI：10.1134/s1070328416060075

  日期：2016.7

  axial positions (axial angles CSbO are 178.01(6)°, 177.74(7)°, and 174.42(11)° and Sb–O angles are 2.244(1), 2.230(2), and 2.507(3) Å). In crystal III, the CSbC angles in the tetrahedral cation [(4-MeC6H4)4Sb]+ are 103.6(2)°–116.22(2)°. A weak interaction is observed between the cation and picrate anion [OC6H2(NO2)3-2,4,6]–(Sb···O distance is 3.472(3) Å).

  四（对甲苯基）锑氧化物，[（4-MeC 6 H 4）4 SbOC 6 H 3 Cl 2 -2,6]•1 / 2TolH（IА，IВ），（4-MeC 6 H 4）4 SbOC 6 H 3（NO 2）2 -2,4（II）和（4-MeC 6 H 4）4 SbOC 6 H 2（NO 2）3 -2,4,6（III）是通过五对对甲苯基苯甲酸与甲苯中的2,6-二氯苯酚，2,4-二硝基苯酚和2,4,6-三硝基苯酚反应而合成的。通过X射线衍射分析（CIF文件CCDC 1050584（I），1433797（II）和999305（III））确定合成的化合物的结构。化合物IА，IВ和II中的Sb原子在轴向位置（轴角CSbO为178.01（6）°，177.74（7）°和174.42（11）°）具有扭曲的三角双锥体配位与芳氧基。 –O角为2.244（1），2.230（2）和2.507（3）Å）。在晶体III中，四面体阳离子[（4-MeC6
• Novel coupling reaction of pentaarylantimony with carbon electrophiles
  作者：Masahiro Fujiwara、Mutsuo Tanaka、Akio Baba、Hisanori Ando、Yoshie Souma

  DOI：10.1016/s0022-328x(96)06509-6

  日期：1996.11

  The cross-coupling reactions of pentaarylantimony with organic halides and allyl acetate were studied under various conditions of acetonitrile solvent, palladium catalysts and copper iodide. Acetonitrile solvent enabled a nucleophilic coupling reaction with allylic halides, although a radical reaction and an intramolecular ligand coupling have been regarded as general under other conditions. Palladium

  在乙腈溶剂，钯催化剂和碘化铜的各种条件下，研究了五芳基锑与有机卤化物和乙酸烯丙酯的交叉偶联反应。乙腈溶剂能够与烯丙基卤化物进行亲核偶联反应，尽管在其他条件下自由基反应和分子内配体偶联也被认为是普遍的。钯催化剂对于与乙酸烯丙酯的偶联反应是有效的。碘化铜促进了有机卤化物如碘甲烷和溴乙酸乙酯的反应。在后两种情况下，二芳基的形成是显着的副反应。
• Synthesis and structure of triarylantimony dioximates
  作者：V. V. Sharutin、O. V. Molokova、O. K. Sharutina、A. V. Gerasimenko、M. A. Pushilin

  DOI：10.1007/s11176-005-0041-4

  日期：2004.10

  The reaction of triphenylantimony, hydrogen peroxide and 5-bromo-2-hydroxybenzaldoxime in a 1 : 1 : 2 molar ratio in ether gives triphenylantimony bis(5-bromo-2-hydroxybenzaldoximate). The reaction of penta-p-tolylantimony with the same oxime in toluene yields tri-p-tolylantimony bis(cyclohexanone oximate). According to X-ray data, the Sb atoms in the products have a distorted trigonal bipyramidal coordination with the oximate ligands in axial positions. In triphenylantimony bis(5-bromo-2-hydroxybenzaldoximate), the O-Sb-O angle is 175.49(6)°, and the interatomic distances are as follows, Å: Sb-C 2.095–2.103; Sb-O 2.069(2) and 2.083(2); and Sb⋅⋅⋅N (intermolecular) 2.896(2) and 2.832(2). The respective geometric parameters of tri-p-tolylantimony bis(cyclohexanone oximate) are 174.25(6)°; 2.107–2.117; 2.049(2) and 2.057(2); and 2.890(2) and 2.861(2) Å.

  三苯基锑、过氧化氢和5-溴-2-羟基苯甲肟以1:1:2的摩尔比在醚中反应生成三苯基锑双(5-溴-2-羟基苯甲肟)。五(p-甲基苯基)锑与相同的肟在甲苯中反应生成三(p-甲基苯基)锑双(环己酮肟)。根据X射线数据，产物中的Sb原子具有扭曲的三角双锥配位，肟配体位于轴向。在三苯基锑双(5-溴-2-羟基苯甲肟)中，O-Sb-O角为175.49(6)°，原子间距如下，Å：Sb-C 2.095–2.103；Sb-O 2.069(2)和2.083(2)；以及Sb⋅⋅⋅N（分子间）2.896(2)和2.832(2)。三(p-甲基苯基)锑双(环己酮肟)的几何参数分别为174.25(6)°；2.107–2.117；2.049(2)和2.057(2)；以及2.890(2)和2.861(2) Å。
• A STUDY OF CRYSTAL STRUCTURES OF TETRA(p-TOLYL)ANTIMONY 2,4,6-TRICHLOROPHENOXIDE AND 3,4,5-TRIFLUOROBENZOATE
  作者：V. V. Sharutin、O. K. Sharutina、A. N. Efremov

  DOI：10.1134/s0022476620090085

  日期：2020.9

  penta(p-tolyl)antimony and symmetric antimony derivatives p-Tol3SbХ2. The crystal structures and structural features of compounds 1 and 2, in which antimony atoms have a trigonal bipyramidal coordination of substituents with axially located oxygen-containing ligands, are determined by single crystal X-ray diffraction.

  四（对甲苯基）锑 2,4,6-三氯苯氧化物 p-Tol4SbOC6H2Cl3-2,4,6 (1) 和四（对甲苯基）锑 3,4,5-三氟苯甲酸盐 p-Tol4SbOС(O)C6H2F3-3 ,4,5 (2) 是通过五（对甲苯基）锑与等摩尔量的 2,4,6-三氯苯酚和 3,4,5-三氟苯甲酸在苯溶液中的相互作用合成的。化合物 1 和 2 也可以通过五（对甲苯基）锑和对称锑衍生物 p-Tol3SbХ2 之间的配体再分配反应获得。化合物 1 和 2 的晶体结构和结构特征由单晶 X 射线衍射确定，其中锑原子具有取代基与轴向定位的含氧配体的三角双锥配位。