二烯丙基二溴锡 | 17381-88-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 烯丙基金属
• 中文名称: 二烯丙基二溴锡
• 英文名称: Diallyltin(IV) dibromide
• 英文别名: diallyltin dibromide；Diallyldibromstannan；Diallylzinn-dibromid
• CAS: 17381-88-3
• 化学式: C₆H₁₀Br₂Sn
• 分子量: 360.663
• InChiKey: YLKVXRKJVMGRRR-UHFFFAOYSA-L

物化性质

• 熔点：
  <0°C
• 沸点：
  77-79°C 2mm
• 密度：
  1,864 g/cm3
• 闪点：
  >110°C

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• TSCA：
  No
• 危险类别码：
  R36/37/38
• 危险品运输编号：
  UN 2788
• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  D-甘露糖 、 二烯丙基二溴锡 以 水 为溶剂， 以71%的产率得到1,2,3-trideoxy-D-mann-non-1-enitol
  参考文献：
  名称：

  Organometallic Reactions in Aqueous Media. The Nature of the Organotin Intermediate in the Tin-Mediated Allylation of Carbonyl Compounds

  摘要：

  Allyl bromide and tin reacted in aqueous media to give first allyltin(II) bromide (5) and then diallyltin dibromide (4). Either organotin intermediate can react with carbonyl compounds to give the corresponding homoallylic alcohols. Competitive experiment showed that 5 was more reactive than 4.

  DOI：

  10.1021/jo9901337
• 作为产物：
  描述：

  3-溴丙烯 以84%的产率得到
  参考文献：
  名称：

  BOGA, CARLA;SAVOIA, DIEGO;TAGLIAVINI, EMILIO;TROMBINI, CLAUDIO;UMANI-RONC+, J. ORGANOMET. CHEM., 353,(1988) N 2, C. 177-183

  摘要：

  DOI：

文献信息

• AN EFFICIENT SYNTHESIS OF HOMOALLYL ALCOHOLS BY THE REACTION OF ALLYL HALIDES WITH CARBONYL COMPOUNDS IN THE PRESENCE OF METALLIC TIN
  作者：Teruaki Mukaiyama、Taira Harada

  DOI：10.1246/cl.1981.1527

  日期：1981.11.5

  In the presence of metallic tin, allyl halides were found to react smoothly with carbonyl compounds under mild conditions to give the corresponding homoallyl alcohols in good yields.

  在金属锡的存在下，发现烯丙基卤化物在温和条件下与羰基化合物顺利反应，以良好的产率得到相应的高烯丙醇。
• 4-O-Benzyl-23-O-isopropylidene-L-threose: A useful building block for stereoselective synthesis of monosaccharides
  作者：Teruaki Mukaiyama、Keisuke Suzuki、Tohru Yamada、Fujio Tabusa

  DOI：10.1016/s0040-4020(01)97597-0

  日期：1990.1

  L-tartaric acid is a quite useful four-carbon building block for monosaccharide synthesis. The versatility can be reinforced by the coupled use of stereoselective addition reactions where the suitable choice of organometallics leads to highly anti-selective additions. The building block is particularly useful in the synthesis of rare sugars the versatility of which is demonstrated by the synthesis of some

  可从L-酒石酸容易获得的4-O-苄基-23-O-异亚丙基-L-苏糖是用于单糖合成的相当有用的四碳结构单元。的多功能性可通过使用耦接立体选择性加成反应被增强，其中的有机金属引线的合适的选择，高度抗选择性加法。该结构单元在合成稀有糖中特别有用，稀有糖的多功能性通过一些L-糖的合成以及聚氧乙烯J的正式全合成以收敛的方式得到了证明。
• Asymmetric allylation reactions of achiral aldehydes with diallyltin dibromide by the use of chiral diamines
  作者：Shū Kobayashi、Koichi Nishio

  DOI：10.1016/00404-0399(50)1363-m

  日期：1995.9

  Asymmetric allylation reactions of achiral aldehydes with diallyltin dibromide have been achieved by using a chiral diamine derived from L-proline as a promoter.

  通过使用衍生自L-脯氨酸的手性二胺作为促进剂，已经实现了非手性醛与二烯丙基二溴化物的不对称烯丙基化反应。
• Asymmetric Allylation of Aldehydes Catalyzed by Simple Dual Small Organic Molecules: L-Proline and L-Prolinol
  作者：Guo-hong Chen、Ling-yan Liu、Xiao-ning Wei、Wei-xing Chang、Jing Li

  DOI：10.1246/cl.2010.1013

  日期：2010.9.5

  A novel and simple methodology for the asymmetric allylation of aldehydes was reported. Double small organic molecules such as l-proline and l-prolinol were first employed for providing a chiral environment so as to afford chiral homoallylic alcohols in high yields and moderate enantioselectivities in our protocol.

  报道了一种新颖且简单的用于醛的不对称烯基化的方法。首次使用了双小有机分子如L-脯氨酸和L-脯氨醇，提供手性环境，从而在我们的方案中获得了高产率和中等对映选择性的手性同烯醇。
• Double Nucleophilic Addition of Azide and Tetraallyltin to the Latent α,β-Unsaturated Aldehydes Using in situ Hydrolysis of the Imino Functionality Promoted by Tin(IV) Chloride Pentahydrate
  作者：Makoto Shimizu、Takafumi Nishi

  DOI：10.1055/s-2004-820023

  日期：——

  In the presence of SnCl4·5H2O and acetic acid, a mixture of trimethylsilyl azide and tetraallyltin underwent 1,4- and sub­sequently 1,2-addition, respectively, with the α,β-unsaturated ­aldimines to give 1,3-hydroxy azides in good yields, where the hydrolysis of the intermediary imino species was found to be crucial.

  在SnCl4·5H2O和醋酸的存在下，三甲基硅烷叠氮化物和四烯基锡的混合物与α,β-不饱和醛亚胺分别发生了1,4-和随后1,2-加成，生成了产率良好的1,3-羟基叠氮化物，其中中间亚胺物种的水解被发现是关键步骤。