苄基三丁基锡烷 | 28493-54-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苄基三丁基锡烷
• 英文名称: benzyltributyltin
• 英文别名: benzyltributylstannane；benzyltri-n-butyltin；tributylbenzylstannane
• CAS: 28493-54-1
• 化学式: C₁₉H₃₄Sn
• 分子量: 381.189
• InChiKey: CFIHCJJFWPTAOV-UHFFFAOYSA-N

物化性质

• 沸点：
  129-130 °C(Press: 0.18 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  6.62
• 重原子数：
  20
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 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：

  苄基三丁基锡烷 在 甲醇 、 copper(II) bis(tetrafluoroborate) 作用下， 以 乙腈 为溶剂， 以94%的产率得到苄甲醚
  参考文献：
  名称：

  在 Cu(II) 盐存在下通过光诱导电子转移从 14 族有机金属化合物生成有机阳离子

  摘要：

  在Cu(BF4)2 存在下，芳甲基硅烷、锗烷或锡烷的乙腈-醇(3:1)溶液的辐照通过芳甲基阳离子以良好的产率得到烷基芳甲基醚。这种光反应的效率以 Si- < Ge- < Sn-化合物的顺序增加。

  DOI：

  10.1246/cl.1988.229
• 作为产物：
  描述：

  ethyl 2-(tributylstannyl)acetate 以 乙醚 、 苯 为溶剂， 生成 苄基三丁基锡烷
  参考文献：
  名称：

  Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Sn: Org.Verb.2, 1.1.2.5.2, page 276 - 305

  摘要：

  DOI：
• 作为试剂：
  描述：

  对氰基苯乙酮 在 苄基三丁基锡烷 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以14%的产率得到1,2-二苯乙烷
  参考文献：
  名称：

  SET and Exciplex Pathways in the Photochemical Reactions between Aromatic Ketones and Benzylsilane and Stannane Derivatives

  摘要：

  The photochemical reaction of alpha,alpha,alpha-trifluoroacetophenone (TFA), benzophenone, and p-cyanoacetophenone with benzyltrimethylsilane in MeCN involves hydrogen transfer from the benzylic position. Desilylation occurs as a minor process only in the case of TFA (but it increases greatly in the presence of MeOH or LiClO4). The final products result from the statistical recombination of the benzyl and ketyl radicals. Further cases of intramolecular selectivity studied are p-methylbenzyl- and p-methoxybenzyltrimethylsilane (the latter substrate undergoes mainly C-Si bond cleavage in the reaction with TFA) as well as benzyltributylstannane (only destannylation observed with all ketones). Product studies are complemented by the determination of relevant kinetic parameters through steady-state and flash-photolysis experiments. The results are explained in terms of hydrogen transfer proceeding from an exciplex and desilylation from the solvent separated radial ion pair. The latter species predominates when Delta G(et) < -10 kcal mol(-1).

  DOI：

  10.1021/ja00135a003

文献信息

• Oxidation of benzylsilanes and benzyltins by oxovanadium(V) compound and molecular oxygen
  作者：Toshikazu Hirao、Chihiro Morimoto、Takashi Takada、Hidehiro Sakurai

  DOI：10.1016/s0040-4020(01)00352-0

  日期：2001.6

  Benzylsilane and benzyltin compounds were oxidized by oxovanadium(V) compound under an oxygen atmosphere to afford the corresponding aromatic aldehydes (ketones) and/or carboxylic acids. In the reaction of benzyltins, oxovanadium(V) compound can be reduced to 0.5 molar amounts. The reaction of benzylsilanes is considered to proceed via electron-transfer process. On the other hand, benzyltins may undergo

  在氧气氛下，通过氧杂钒（V）化合物氧化苄基硅烷和苄基锡化合物，得到相应的芳族醛（酮）和/或羧酸。在苄基锡的反应中，氧钒（V）化合物可以减少至0.5摩尔量。苄基硅烷的反应被认为是通过电子转移过程进行的。另一方面，苄基锡可能会发生金属转移反应以生成苄基钒物种，它们会通过非自由基过程直接转移到羰基化合物上。
• 8-arylalkyl- and
  申请人：Boehringer Ingelheim Pharmaceuticals, Inc.

  公开号：US05705499A1

  公开（公告）日：1998-01-06

  Disclosed are novel 8-arylalkyl-5,11-dihydro-6H-dipyrido\x9b3,2-b:2',3'-e!\x9b1,4!diazepines. These are useful in the treatment of HIV-1 infection.

  公开的是新型的8-芳基烷基-5,11-二氢-6H-二吡啶[3,2-b:2',3'-e]![1,4]二氮杂环。这些化合物在治疗HIV-1感染中是有用的。
• Synthesis of organotrialkylstannanes. The reaction between organic halides and hexaalkyldistannanes in the presence of palladium complexes
  作者：Hormoz Azizian、Colin Eaborn、Alan Pidcock

  DOI：10.1016/s0022-328x(00)84615-x

  日期：1981.7

  give YC6H4CH2SnR3 for (a) R = n-Bu, Y = H, m-OMe, p-OMe, m-Cl, m-CN, and m-NO2, and (b) R = Me, Y = m-Cl, m-CN, p-CN and m-NO2. These reactions are of special value as preparative procedures in cases in which Grignard or organolithium reagents cannot be used. Allyl chloride and bromide were likewise shown to react with (n-Bu3Sn)2 to give CH2CHCH2SnBu3, but n-BuCl and n-BuBr gave only a trace of n-Bu4Sn

  在[Pd（PPh 3）]存在下，芳基卤化物YC 6 H 4 X（X = Br或I）与二萘烷（R 3 Sn）2（R = n-Bu或Me）在甲苯中反应。4 ]或[PDBR 2（PPH 3）2 ]，得到化合物YC 6 ħ 4 SNR 3用于：（a）R =正丁基，Y = H，p-OME，ö -Me，p -Me，米- Cl，p -Cl，m -CN，p -COCH 3和m -NO 2和（b）R = Me，Y = H，p -OMe，p -Me，p -CN，p -COCH 3，m -NO 2和p -NO 2。苄基卤YC 6 ħ 4 CH 2 X（X = Cl或Br）类似地得到YC 6 ħ 4 CH 2 SNR 3用于：（a）R =正丁基，Y = H，米-OMe，p -OMe，米- Cl，m -CN和m -NO 2，以及（b）R = Me，Y = m -Cl，m-CN，p -CN和m -NO 2。在不能使用
• Pyrazolo-pyridine derivatives as ligands for GABA receptors
  申请人：Merck Sharp & Dohme Ltd.

  公开号：US06333336B1

  公开（公告）日：2001-12-25

  Pyrazolo[4,3-c]pyridin-3-one derivatives substituted at the 2-position by an optionally substituted aryl or heteroaryl moiety, and having pendant substituents at the 7-position and optionally also at the 6-position, are selective ligands for GABAA receptors, particularly having high affinity for the &agr;2 and/or &agr;3 subunit, and are useful in the treatment and/or prevention of disorders of the central nervous system, including anxiety and convulsions.

  吡唑并［4,3-c］吡啶-3-酮衍生物在2位被一个可选择取代的芳基或杂环芳基取代，并在7位具有挂链取代基，也可在6位具有可选择的取代基，是GABAA受体的选择性配体，特别具有对α2和/或α3亚基的高亲和力，并且在治疗和/或预防中枢神经系统疾病，包括焦虑和惊厥方面具有用处。
• Ultrasound promoted Barbier reactions and Csp3–Csp2 Stille coupling for the synthesis of diarylmethanes and substituted benzophenones
  作者：Romina A. Ocampo、Liliana C. Koll、Sandra D. Mandolesi

  DOI：10.1016/j.ultsonch.2012.06.014

  日期：2013.1

  Stille coupling under palladium catalysis between some substituted aryl compounds and benzyltributyltin compounds generated through sonicated Barbier reaction in a very short time reaction and excellent yield. The study reported below compares different methods to optimize the synthesis of usually unstable benzyltin derivatives and is another contribution to the investigation of Csp(3)-Csp(2) coupling

  在这里，我们介绍了在超声催化的巴比尔反应中，在很短的时间内就通过超声斯蒂勒偶合在钯催化下，在一些取代的芳基化合物和苄基三丁基锡化合物之间获得的各种二芳基甲烷的制备方法。以下报道的研究比较了优化通常不稳定的苄基锡衍生物合成的不同方法，这是对涉及苄基-芳基试剂的Csp（3）-Csp（2）偶联过程研究的另一贡献。通过某些二芳基甲烷的氧化，可以容易地以非常好的收率制备取代的羧化二苯甲酮。