(2,4,6-tris{bis(trimethylsilyl)methyl}phenyl)SnCl3 | 135139-65-0

• 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: (2,4,6-tris{bis(trimethylsilyl)methyl}phenyl)SnCl3
• 英文别名: (2,4,6-tris(bis(trimethylsilyl)methyl)phenyl)trichlorostannane；TbtSnCl3；((Me3Si)2CH)3C6H2SnCl3；[[3,5-bis[bis(trimethylsilyl)methyl]-2-trichlorostannylphenyl]-trimethylsilylmethyl]-trimethylsilane
• CAS: 135139-65-0
• 化学式: C₂₇H₅₉Cl₃Si₆Sn
• 分子量: 777.347
• InChiKey: CVLIVVUKUSSXTI-UHFFFAOYSA-K

计算性质

• 辛醇/水分配系数(LogP)：
  11.06
• 重原子数：
  37.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  (2,4,6-tris{bis(trimethylsilyl)methyl}phenyl)SnCl3 在 n-BuLi 、 LiAlH₄ 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 2-(2,4,6-tris(bis(trimethylsilyl)methyl)phenyl)-2-bromo-3-tert-butyl-1,2-dihydro-2-stannanaphthalene
  参考文献：
  名称：

  稳定的中性锡芳族化合物：动力学稳定的 2-锡萘的合成、结构和络合

  摘要：

  动力学稳定的 2-锡萘是第一个含有锡原子的稳定中性芳香族化合物的例子，已被合成并充分表征。该化合物的光谱和晶体结构分析以及使用模型化合物的理论计算结果强烈表明，它与萘一样具有离域的 10pi 电子环系统。此外，发现它在与 [Cr(CH3CN)3(CO)3] 的配体交换反应中充当 eta6-芳烃配体，产生第一个稳定的 eta6-2-锡萘铬配合物。

  DOI：

  10.1021/ja057531d
• 作为产物：
  描述：

  四氯化锡 、 1-bromo-2,4,6-tris[bis(trimethylsilyl)methyl]benzene 在 t-C₄H₉Li 作用下， 以 四氢呋喃 为溶剂， 以54%的产率得到(2,4,6-tris{bis(trimethylsilyl)methyl}phenyl)SnCl3
  参考文献：
  名称：

  Synthesis and structure of 1,2,3,4,5-tetrachalcogenastannolanes

  摘要：

  Novel cyclic polychalcogenides, 1,2,3,4,5-tetrathia- and tetraselenastannolanes [Tb(R)Sny4 (Y = S, Se; Tb = 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl; R = mesityl or 2,4,6-triisopropylphenyl)], have been synthesized by two routes, i.e., (a) the reaction of dihydrostannanes Tb(R)SnH2 with sulfur or selenium and (b) the lithiation of dihydrostannanes Tb(R)SnH2 or dichlorostannanes Tb(R)SnCl2 with t-BuLi followed by reaction with sulfur or selenium. All the tetrachalcogenastannolanes have been characterized by H-1 and C-13 NMR and elemental analysis. In addition, Tb(Mes)SnS4 (7b) and Tb(Mes)SnSe4 (8b) have been subjected to single-crystal X-ray diffraction analysis. Both five-membered 7b and 8b have distorted envelope conformation, the former of which is slightly more distorted. The reason for the exclusive formation of five-membered polychalcogenides has been discussed on the basis of the X-ray structural analysis and ab initio calculations for the model ring system H2SiSn (n = 2-6).

  DOI：

  10.1021/om00028a059

文献信息

• Synthesis and properties of stable 2-metallanaphthalenes of heavier group 14 elements
  作者：Yoshiyuki Mizuhata、Takahiro Sasamori、Noriyoshi Nagahora、Yasuaki Watanabe、Yukio Furukawa、Norihiro Tokitoh

  DOI：10.1039/b718193k

  日期：——

  The first stable neutral stannaaromatic compound, 2-stannanaphthalene , was synthesized by taking advantage of an extremely bulky and efficient steric protection group, 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl (Tbt). The molecular structure and aromaticity of were discussed on the basis of X-ray crystallographic analysis, NMR, UV-vis, and Raman spectroscopy, cyclic voltammetry, and theoretical calculations

  第一个稳定的中性锡烷基芳族化合物2-stannanaphthalene是利用一个非常庞大和有效的空间保护基团2,4,6-三[双（三（三甲基甲硅烷基）甲基]苯基（Tbt）合成的。在X射线晶体学分析，NMR，UV-vis和拉曼光谱，循环伏安法和理论计算的基础上，讨论了其分子结构和芳香性。合成了具有相似于2的骨架的2-锗金属萘进行比较，并系统地阐明了含有更重的14族元素（Si，Ge或Sn）的2-metallanaphthalene系统的性能。
• Generation of 9-Stannaphenanthrene and Its Reactivities
  作者：Yoshiyuki Mizuhata、Nobuhiro Takeda、Takahiro Sasamori、Norihiro Tokitoh

  DOI：10.1246/cl.2005.1088

  日期：2005.8

  A neutral stannaaromatic compound, 9-stannaphenanthrene 1a bearing an efficient steric protection group, 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl (Tbt), was successfully generated by the reaction of the corresponding chlorostannane 2 with lithium 2,2,6,6-tetramethylpiperidide in THF at −78 °C. The generaion of 1a was indicated by the trapping experiments using MeOD, Mes*CNO, and 2,3-dimethyl-1,3-butadiene at the same temperature. However, 1a was found to undergo ready dimerization at room temperature to give the cis-[2 + 2] dimer 3 stereoselectively.

  在-78 °C的四氢呋喃中，相应的氯甾烷 2 与 2,2,6,6-四甲基哌啶锂反应，成功生成了一种中性链烷族化合物 9-链菲 1a，该化合物带有一个高效的立体保护基团 2,4,6-三[双（三甲基硅基）甲基]苯基 (Tbt)。在相同温度下使用 MeOD、Mes*CNO 和 2,3-二甲基-1,3-丁二烯进行的捕集实验表明生成了 1a。然而，研究发现 1a 在室温下可立即发生二聚反应，从而立体选择性地生成顺式[2 + 2]二聚体 3。
• Generation of stannabenzenes and their monomer–dimer equilibration
  作者：Yoshiyuki Mizuhata、Shiori Fujimori、Naoya Noda、Shuhei Kanesato、Norihiro Tokitoh

  DOI：10.1039/c8dt02994f

  日期：——

  high reactivity. In order to synthesize and isolate a stable stannabenzene, we have introduced two steric protection groups, the Tbt (2,4,6-tris[bis(trimethylsilyl)methyl]phenyl) or the Bbt (2,6-bis[bis(trimethylsilyl)methyl]-4-[tris(trimethylsilyl)methyl]phenyl) group on the tin atom and the t-butyl group on the 2-position, to the stannabenzene skeleton. Such a combination of steric protection groups

  迄今为止，尚未分离出锡烷苯，因为它具有很高的反应活性。为了合成和分离稳定的锡烷基苯，我们引入了两个空间保护基团，即Tbt（2,4,6-三[双（三（三甲基甲硅烷基）甲基]苯基]苯基）或Bbt（2,6-双[二[三（三甲基甲硅烷基）甲基]苯基]锡原子上的）甲基] -4- [三（三甲基（三甲基甲硅烷基）甲基]苯基]基团和2位置的叔丁基与锡烷苯骨架相连。发现这种空间保护基的组合在一定程度上抑制了锡烷苯的二聚作用，得到了相应的锡烷苯及其二聚体的平衡混合物。
• Generation of Stannabenzenes and Their Properties
  作者：Yoshiyuki Mizuhata、Naoya Noda、Norihiro Tokitoh

  DOI：10.1021/om100382n

  日期：2010.11.8

  Stannabenzenes 3, neutral stannaaromatic compounds having the simplest aromatic unit, were successfully generated by the reaction of the corresponding bromostannanes 5-Br with diisopropylamide mm, hexane at -40 degrees C. The generation of 3 was indicated by the formation of the [4 + 2] dimer 6 at room temperature. The thermal stability of 3 was completely different from that of the sila- and germabenzenes bearing the same substituent. The structural and electronic properties of stannabenzene were estimated by theoretical calculations.
• Tokitoh, Norihiro; Takahashi, Masaki; Matsumoto, Tsuyoshi, Phosphorus, Sulfur and Silicon and the Related Elements
  作者：Tokitoh, Norihiro、Takahashi, Masaki、Matsumoto, Tsuyoshi、Suzuki, Hiroyiki、Matsuhashi, Yasusuke、et al.

  DOI：——

  日期：——