Dibutylbis(2-methylphenyl)stannane

• 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: Dibutylbis(2-methylphenyl)stannane
• 英文别名: Sn(n-Bu)2(o-tolyl)2；dibutyl-bis(2-methylphenyl)stannane
• 化学式: C₂₂H₃₂Sn
• 分子量: 415.206
• InChiKey: OULDVNRLVTXKLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.47
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  Dibutylbis(2-methylphenyl)stannane 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 N-<(2-Methylphenyl)sulfonyl>-2-methylbenzenecarboxamide
  参考文献：
  名称：

  Tin for organic synthesis. 10. Unconventional regiospecific syntheses of aromatic carbonamides and thiocarbonamides by means of tin-mediated Friedel-Crafts reactions

  摘要：

  Friedel-Crafts reactions of stannylarenes 1 with tosyl isocyanate (TsNCO, 2) give N-tosylcarbonamides 3 via ipso substitution of the stannyl group. Thus, unconventionally substituted aromatic carbonamides can be obtained. The combination of the reaction of 1 and 2 with that of 1 and chlorosulfonyl isocyanate (14) allows one-pot syntheses of N-(arylsulfonyl)-substituted aromatic carbonamides with optional substitution patterns on both aromatic rings. The known ipso-specific substitutions of stannylarenes with 14 are extended to bi- and tricyclic arenes as well as to thiophenes 6 and 22. One stannyl group can serve as a leaving group for two aromatic systems, as shown with diaryldialkyltins 29. Also, stannylalkanes such as 27 react with 14 to afford alkylsulfonyl isocyanates and products of further reactions, such as 28. From the reactions of 1 with ethoxycarbonyl isothiocyanate (32), ortho- and meta-substituted aromatic thiocarbonamides 33 which are potential precursors for further syntheses, are accessible. The scope, limitations, and mechanism of these electrophilic substitutions are outlined.

  DOI：

  10.1021/jo00077a020
• 作为产物：
  描述：

  邻甲苯基溴化镁 、 二丁基二氯化锡 以 乙醚 为溶剂， 以76%的产率得到Dibutylbis(2-methylphenyl)stannane
  参考文献：
  名称：

  方便快速合成SnBu 2 RCl衍生物

  摘要：

  已经开发了一种使用微波辐射和酸性氧化铝柱色谱法快速制备SnBu 2 RX（Bu = n -Bu）的简便方法。该方法可以是一种很好的选择，特别是对于出于测试目的的简便快速制备，以及通常用于合成由于热不稳定性或低挥发性而无法通过分馏纯化的化合物的合成而言。

  DOI：

  10.1021/om900326g

文献信息

• Tin for Organic Synthesis, 14. Synthesis of Aromatic and α,β‐Unsaturated Aldehydes by a Friedel‐Crafts‐like Electrophilic Destannylation Using 1,1‐Dichloromethyl Methyl Ether
  作者：Michael Niestroj、Wilhelm P. Neumann†

  DOI：10.1002/cber.19961290111

  日期：1996.1

  for the preparation of a variety of aromatic (7a–m), heteroaromatic (7n–r), and α,β-unsaturated aldehydes (8a–f) is described. The reaction of trialkylaryl- (2a–o), heteroaryl- (2p–t), and 1-alkenylstannanes (4a–f and 5a–f) with dichloromethyl methyl ether (1, DCME) in the presence of aluminium trichloride followed by hydrolysis provides the corresponding aldehydes. In the case of arylstannanes the ipso-isomers

  描述了一种温和有效的方法，用于制备各种芳族化合物（7a–m），杂芳族化合物（7n–r）和α，β-不饱和醛（8a–f）。在三氯化铝存在下，三烷基芳基-（2a-o），杂芳基-（2p-t）和1-烯基锡烷（4a-f和5a-f）与二氯甲基甲基醚（1，DCME）反应，然后水解提供相应的醛。在arylstannanes的情况下，本位-异构体通常形成; 所述p -alde-海兹发生作为副产物。1-烯基锡烷的亲电取代为1会以ipso和立体定向方式生成α，β-不饱和醛。苯乙烯基和甲硅烷基的离去能力的比较表明，甲硅烷基取代的化合物6a-c对亲电子试剂1的反应性较低，甚至为零。在甲硅烷基锡烯基烯6c中，只有锡烷基反应，而锡11的功能在产物醛11中保持不受影响。
• Tin for organic synthesis. 10. Unconventional regiospecific syntheses of aromatic carbonamides and thiocarbonamides by means of tin-mediated Friedel-Crafts reactions
  作者：Martin Arnswald、Wilhelm P. Neumann

  DOI：10.1021/jo00077a020

  日期：1993.12

  Friedel-Crafts reactions of stannylarenes 1 with tosyl isocyanate (TsNCO, 2) give N-tosylcarbonamides 3 via ipso substitution of the stannyl group. Thus, unconventionally substituted aromatic carbonamides can be obtained. The combination of the reaction of 1 and 2 with that of 1 and chlorosulfonyl isocyanate (14) allows one-pot syntheses of N-(arylsulfonyl)-substituted aromatic carbonamides with optional substitution patterns on both aromatic rings. The known ipso-specific substitutions of stannylarenes with 14 are extended to bi- and tricyclic arenes as well as to thiophenes 6 and 22. One stannyl group can serve as a leaving group for two aromatic systems, as shown with diaryldialkyltins 29. Also, stannylalkanes such as 27 react with 14 to afford alkylsulfonyl isocyanates and products of further reactions, such as 28. From the reactions of 1 with ethoxycarbonyl isothiocyanate (32), ortho- and meta-substituted aromatic thiocarbonamides 33 which are potential precursors for further syntheses, are accessible. The scope, limitations, and mechanism of these electrophilic substitutions are outlined.
• A Convenient Quick Synthesis of SnBu₂RCl Derivatives
  作者：Nora Carrera、Mónica H. Pérez-Temprano、Ana C. Albéniz、Juan A. Casares、Pablo Espinet

  DOI：10.1021/om900326g

  日期：2009.7.13

  the quick preparation of SnBu2RX (Bu = n-Bu) has been developed using microwave irradiation and column chromatography in acidic alumina. The method can be a good alternative particularly for easy and quick preparation of small amounts for test purposes and, in general, for the synthesis of compounds that cannot be purified by fractional distillation due to thermal lability or low volatility.

  已经开发了一种使用微波辐射和酸性氧化铝柱色谱法快速制备SnBu 2 RX（Bu = n -Bu）的简便方法。该方法可以是一种很好的选择，特别是对于出于测试目的的简便快速制备，以及通常用于合成由于热不稳定性或低挥发性而无法通过分馏纯化的化合物的合成而言。