(4-甲氧苄基)三甲基锡烷 | 51755-57-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (4-甲氧苄基)三甲基锡烷
• 英文名称: (4-Methoxybenzyl)trimethylstannane
• 英文别名: (CH3)3SnCH2C6H4-p-OCH3；(4-Methoxyphenyl)methyl-trimethylstannane
• CAS: 51755-57-8
• 化学式: C₁₁H₁₈OSn
• 分子量: 284.973
• InChiKey: FZLJMIBNDCICRE-UHFFFAOYSA-N

物化性质

• 沸点：
  282.1±42.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4-甲氧苄基)三甲基锡烷 、 4-(6-iodo-imidazo[1,2-a]pyridin-2-yl)-N,N-dimethylbenzenamine 在 tris(dibenzylideneacetone)dipalladium (0) 作用下， 以 甲苯 为溶剂， 150.0 ℃ 、2.07 MPa 条件下， 反应 0.17h， 以85%的产率得到4-(6-(4-methoxybenzylthio)-imidazo[1,2-a]pyridin-2-yl)-N,N-dimethylbenzenamine
  参考文献：
  名称：

  Rapid palladium-catalyzed cross-coupling in the synthesis of aryl thioethers under microwave conditions

  摘要：

  A Pd-catalyzed coupling of aromatic iodides or bromides and tin-thiolates under microwave conditions was developed to synthesize aromatic thioethers without concomitant formation of the reduced products. Ligand screening revealed DiPPF and BINAP-Tol as the most generally useful ligands for this transformation. A variety of iodides or bromides were coupled to give the thioethers rapidly (10 min) in 60-95% isolated yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.04.049
• 作为产物：
  描述：

  (trimethylstannyl)lithium 、 4-甲氧基氯苄 以 乙醚 为溶剂， 以55%的产率得到(4-甲氧苄基)三甲基锡烷
  参考文献：
  名称：

  二氧化硫插入苄基三甲基锡的动力学和机理

  摘要：

  制备了一系列间位和对位取代的苄基三甲基锡烷，并通过1 H NMR法动力学研究了它们与二氧化硫在甲醇溶剂中于30°的反应。不论取代基是什么（m-和p -CH 3，m-和p -CF 3，m-和p -Cl，m-和p -OCH 3），并且该反应在至少70％的反应中显示出良好的二级动力学。该反应的显着特征是速率对取代基的相对不敏感性，最大的影响是p -CF 3速率提高了2.2 。虽然这表明过渡态的苄基碳有一定的碳负离子特征发展，但电子不给力基团m-和p -CH 3引起速率略有增加（分别为1.2和1.07）这一事实也表明，反应机理随着温度的变化而变化。取代基，并带有电荷以使其最好地被取代基分散。

  DOI：

  10.1016/s0022-328x(00)95038-1

文献信息

• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Sn: Org.Verb.2, 1.1.2.1.2, page 20 - 31
  作者：

  DOI：——

  日期：——
• Oxidation of Benzyltrialkylstannanes by Iodosylbenzene Catalyzed by Iron Tetrakis(pentafluorophenyl)porphyrin Chloride. Possible Role of Benzyloxy Radicals
  作者：Enrico Baciocchi、Marcella Ioele

  DOI：10.1021/jo00122a032

  日期：1995.9

  The oxidations of some benzyltrialkylstannanes by iodosylbenzene induced by tetrakis(pentafluorophenyl)porphyrin chloride (TPFP)FeCl have been investigated. Benzaldehydes and benzyl alcohols are the main reaction products, accompanied by minor amounts of 1,2-diarylethanes and benzyl chlorides. A mechanism seems likely involving the formation of a benzyltrialkylstannane cation radical, which undergoes C-Sn bond cleavage to afford a benzyl radical. The formation of 1,2-diarylethane from this radical is straightforward, whereas it is suggested that benzyl alcohol and benzaldehyde result from the disproportionation of a benzyloxy radical, formed in a oxygen transfer reaction from iodosylbenzene to the benzyl radical. In CH2Cl2, benzyl alcohol can also be the result of hydrogen atom abstraction from the solvent by the benzyloxy radical.
• Highly regio- and chemo-selective γ-addition of benzylic group to N-alkoxycarbonylpyridiniuin salts by means of organotin reagent
  作者：Ryohei Yamaguchi、Masataka Moriyasu、Mituyosi Kawanisi

  DOI：10.1016/s0040-4039(00)83979-9

  日期：1986.1
• YAMAGUCHI, RYOHEI;MORIYASU, MASATAKA;KAWANISI, MITUYOSI, TETRAHEDRON LETT., 1986, 27, N 2, 211-214
  作者：YAMAGUCHI, RYOHEI、MORIYASU, MASATAKA、KAWANISI, MITUYOSI

  DOI：——

  日期：——
• Sulfur dioxide insertion into benzyltrimethylstannanes: kinetics and mechanism
  作者：Christopher J. Moore、William Kitching

  DOI：10.1016/s0022-328x(00)95038-1

  日期：1973.10

  series of meta- and para-substituted benzyltrimethylstannanes have been prepared and their reactions with sulfur dioxide in methanol solvent at 30° have been studied kinetically by an 1H NMR method. Insertion occurs exclusively into the benzyl—tin bond, irrespective of substituent (m- and p-CH3, m- and p-CF3, m- and p-Cl, m- and p-OCH3), and the reaction exhibits good second-order kinetics for at least

  制备了一系列间位和对位取代的苄基三甲基锡烷，并通过1 H NMR法动力学研究了它们与二氧化硫在甲醇溶剂中于30°的反应。不论取代基是什么（m-和p -CH 3，m-和p -CF 3，m-和p -Cl，m-和p -OCH 3），并且该反应在至少70％的反应中显示出良好的二级动力学。该反应的显着特征是速率对取代基的相对不敏感性，最大的影响是p -CF 3速率提高了2.2 。虽然这表明过渡态的苄基碳有一定的碳负离子特征发展，但电子不给力基团m-和p -CH 3引起速率略有增加（分别为1.2和1.07）这一事实也表明，反应机理随着温度的变化而变化。取代基，并带有电荷以使其最好地被取代基分散。