trichloro-2-tolylstannane | 51729-82-9

• 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: trichloro-2-tolylstannane
• 英文别名: o-tolyltin trichloride；o-tolylSnCl₃；o-tolyltrichlorotin；Trichloro-(2-methylphenyl)stannane
• CAS: 51729-82-9
• 化学式: C₇H₇Cl₃Sn
• 分子量: 316.202
• InChiKey: XLOVMEQXRGQGAI-UHFFFAOYSA-K

物化性质

• 沸点：
  154-158 °C(Press: 20 Torr)
• 密度：
  1.7619 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• 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：

  trichloro-2-tolylstannane 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.5h， 以50%的产率得到(2-methylphenyl)stannane
  参考文献：
  名称：

  Aryltin chlorides and hydrides: Preparation, detailed NMR studies and DFT calculations

  摘要：

  A series of novel tin chlorides RnSnCl4-n and respective hydrides RnSnH4-n were synthesized displaying a range of substituted phenyl residues, as well as naphthyl moieties (R = Ph, o-tolyl, 2,4-xylyl, 2,6-xylyl, p-biphenyl, 1-naphthyl, 2-naphthyl). These compounds were characterized using H-1, C-13 and Sn-119 NMR spectroscopy. In addition, X-ray diffraction was employed to elucidate the molecular structure of all solid aryltin chlorides (8-10, 14, 15). In each case, the tin is in a distorted tetrahedral environment. All naphthyl containing derivatives exhibit displaced pi-pi stacking. DFT calculations were carried out to compare experimental NMR data with calculated C-13 and Sn-119 shifts, as well as C-13-Sn-119 coupling constants. (C) 2013 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.03.012
• 作为产物：
  描述：

  四氯化锡 、 tetra-o-tolyltin 、 (o-CH3C6H4)3SnBr 反应 2.0h， 以7%的产率得到trichloro-2-tolylstannane
  参考文献：
  名称：

  Aryltin chlorides and hydrides: Preparation, detailed NMR studies and DFT calculations

  摘要：

  A series of novel tin chlorides RnSnCl4-n and respective hydrides RnSnH4-n were synthesized displaying a range of substituted phenyl residues, as well as naphthyl moieties (R = Ph, o-tolyl, 2,4-xylyl, 2,6-xylyl, p-biphenyl, 1-naphthyl, 2-naphthyl). These compounds were characterized using H-1, C-13 and Sn-119 NMR spectroscopy. In addition, X-ray diffraction was employed to elucidate the molecular structure of all solid aryltin chlorides (8-10, 14, 15). In each case, the tin is in a distorted tetrahedral environment. All naphthyl containing derivatives exhibit displaced pi-pi stacking. DFT calculations were carried out to compare experimental NMR data with calculated C-13 and Sn-119 shifts, as well as C-13-Sn-119 coupling constants. (C) 2013 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.03.012

文献信息

• Direct C–H bond arylation of arenes with aryltin reagents catalysed by palladium complexes
  作者：Hiroshi Kawai、Yasuhiro Kobayashi、Shuichi Oi、Yoshio Inoue

  DOI：10.1039/b717251f

  日期：——

  Direct C–H bond arylation of simple arenes with aryltin reagents has been successfully catalysed by PdCl2 in the presence of CuCl2. CuCl2 proved to be an activator for a palladium intermediate as well as an oxidant.

  简单的芳烃与芳基锡试剂直接C–H键芳基化反应，在PdCl2催化下，并存在CuCl2的情况下已成功实现。CuCl2不仅作为钯中间体的活化剂，同时也扮演着氧化剂的角色。
• Palladium-catalyzed carbostannylation by means of reagents containing carbon–tin–halogen inter-element linkages
  作者：Keigo Fugami、Kentaro Kawata、Tatsuki Enokido、Yukie Mishiba、Sachiko Hagiwara、Yasuyuki Hirunuma、Daisuke Koyama、Masayuki Kameyama、Masanori Kosugi

  DOI：10.1016/s0022-328x(00)00483-6

  日期：2000.10

  Reagents containing carbon–tin–halogen inter-element linkages were effective for palladium-catalyzed carbostannylation. In situ generated allyltin trichlorides add to carbon–carbon double bonds of bicyclo[2.2.1]hept-2-ene (norbornene) and bicyclo[2.2.1]hepta-2,5-diene (norbornadiene), stereoselectively, under the catalysis of palladium(0) species in good yields. The regioselectivity of unsymmetrically

  含有碳－锡－卤素元素间键的试剂对于钯催化的羰基化反应有效。原位生成的三氯化烯丙基锡在催化下立体选择性地添加到双环[2.2.1]庚-2-烯（降冰片烯）和双环[2.2.1]七，2,5-二烯（降冰片二烯）的碳-碳双键上钯（0）种类，收率很高。不对称取代的烯丙基试剂的区域选择性随锡（II）盐的选择而显着变化。三氯化芳基锡经历钯催化的降冰片烯的芳基锡烷基化反应，得到的混合物包括一种降冰片烯和两种降冰片烯。产物比例取决于溶剂的选择和芳族取代基的电子性质。
• Mono-aryltin(IV) and mono-benzyltin(IV) complexes with pyridine-2-carboxylic acid and 8-hydroxyquinoline. X-ray structure of p-chloro-phenyl-tris(8-quinolinato)tin(IV)·2CHCl3
  作者：Markus Schürmann、Ralf Schmiedgen、Friedo Huber、Arturo Silvestri、Giuseppe Ruisi、Adriana Barbieri Paulsen、Renato Barbieri

  DOI：10.1016/s0022-328x(99)00103-5

  日期：1999.7

  o- and p-ClC6H4=o- and p-ClPh, o-ClC6H4CH2=o-ClBenzyl; besides, R=Ph in RSn(Ox)3) have been synthesized and characterized by elemental analysis and determination of molecular weights in CHCl3 solutions. The structure of p-ClPhSn(Ox)3·2CHCl3 has been determined by X-ray diffractometry. The 7-coordinated tin atom of the monomeric compound is in the center of a pentagonal bipyramid formed by (p-ClPh)C and

  络合物RSn（O 2 CPy）3 ·2H 2 O和RSn（Ox）3，（PyCOOH =吡啶-2-羧酸，HOx = 8-羟基喹啉，R = o-和p -Tolyl，o-和p -ClC 6 H 4 = o-和p -ClPh，o-ClC 6 H 4 CH 2 = o-苄基；此外，合成了RSn（Ox）3）中的R = Ph并通过元素分析和分子量测定确定CHCl 3溶液。p -ClPhSn（Ox）的结构3 ·2CHCl 3已通过X射线衍射法测定。单体化合物的7-协调锡原子是由形成的五角双锥的中心（p -ClPh）C和O与螯合牛的N原子-配体。后者类型的结构将根据适用于所有的配合物119的Sn穆斯堡尔（包括动态的确定119的Sn核）和在固体状态IR光谱; 所述配体- Ò 2 CPY出现通过COO的一个氧原子螯合锡-基团和N原子，尽管一种螯合剂和两个单齿的发生PyCO 2 -配体（通过COO - ），并协调由H
• Stille Cross-Couplings of Unactivated Secondary Alkyl Halides Using Monoorganotin Reagents
  作者：David A. Powell、Toshihide Maki、Gregory C. Fu

  DOI：10.1021/ja0436300

  日期：2005.1.1

  The first catalyst that achieves Stille cross-couplings of secondary (as well as primary) alkyl halides has been developed. The method employs easily handled and inexpensive catalyst components (NiCl2 and 2,2'-bipyridine) and, through the use of monoorganotin reagents, avoids the formation of toxic and difficult-to-remove triorganotin side products.
• Aryltin chlorides and hydrides: Preparation, detailed NMR studies and DFT calculations
  作者：Cathrin Zeppek、Johann Pichler、Ana Torvisco、Michaela Flock、Frank Uhlig

  DOI：10.1016/j.jorganchem.2013.03.012

  日期：2013.9

  A series of novel tin chlorides RnSnCl4-n and respective hydrides RnSnH4-n were synthesized displaying a range of substituted phenyl residues, as well as naphthyl moieties (R = Ph, o-tolyl, 2,4-xylyl, 2,6-xylyl, p-biphenyl, 1-naphthyl, 2-naphthyl). These compounds were characterized using H-1, C-13 and Sn-119 NMR spectroscopy. In addition, X-ray diffraction was employed to elucidate the molecular structure of all solid aryltin chlorides (8-10, 14, 15). In each case, the tin is in a distorted tetrahedral environment. All naphthyl containing derivatives exhibit displaced pi-pi stacking. DFT calculations were carried out to compare experimental NMR data with calculated C-13 and Sn-119 shifts, as well as C-13-Sn-119 coupling constants. (C) 2013 Elsevier B. V. All rights reserved.