phenyldimethyl(2-bromo-2-propenyl)-silane | 122244-66-0

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: phenyldimethyl(2-bromo-2-propenyl)-silane
• 英文别名: 2-bromo-3-dimethylphenylsilylprop-1-ene；2-bromo-3-dimethyl(phenyl)silylpropene；2-Bromoprop-2-enyl-dimethyl-phenylsilane
• CAS: 122244-66-0
• 化学式: C₁₁H₁₅BrSi
• 分子量: 255.23
• InChiKey: JCJDCUIACUDRMU-UHFFFAOYSA-N

物化性质

• 沸点：
  269.3±33.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  phenyldimethyl(2-bromo-2-propenyl)-silane 在 偶氮二异丁腈 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 4-(1'-dimethylphenylsilylmethylethenyl)dihydro-2(3H)-furanone
  参考文献：
  名称：

  Preparation of A Trifunctional Allylsilane for Use in Three-Bond Cascade Reactions

  摘要：

  The synthesis of trifunctional allylsilane (2b) is described.

  DOI：

  10.1080/00397919608003719
• 作为产物：
  描述：

  苯基二甲基氯硅烷 、 2,3-二溴-1-丙烯 生成 phenyldimethyl(2-bromo-2-propenyl)-silane
  参考文献：
  名称：

  Selective mono- and polymethylene homologations of copper reagents using (iodomethyl)zinc iodide

  摘要：

  A wide range of unsaturated aryl-, alkenyl-, alkynylcopper compounds can be selectively homologated by a methylene unit using (iodomethyl)zinc iodide or bis(iodomethyl)zinc. These reactions allow the generation of mixed allylic zinc-copper compounds which can be efficiently trapped with carbonyl compounds. An application to a general preparation of functionalized alpha-methylene-gamma-butyrolactones is described. The homologation of alkynylcoppers with (iodomethyl)zinc iodide allows a one-pot preparation of propargylic copper reagents which in the presence of a carbonyl compound provide various homopropargylic alcohols in excellent yields. In the absence of an electrophile, a clean quadruple methylene homologation of alkynylcoppers occurs to furnish dienic copper reagents. The homologation of other types of copper reagents is also possible, and carbanions at the alpha-position to amines as well as homoenolates of aldehydes or ketones can also be prepared by this method.

  DOI：

  10.1021/jo00062a010

文献信息

• The silyl-cupration and stannyl-cupration of allenes
  作者：Ian Fleming、Michael Rowley、Purificacíon Cuadrado、Ana M. González-Nogal、Francisco J. Pulido

  DOI：10.1016/0040-4020(89)80069-9

  日期：1989.1

  The stoichiometric silyl-cupration of allene 7, followed directly by treating the intermediate cuprate with a proton, with a range of carbon electrophiles, and with chlorine gives the vinylsilanes 8–13. Alternatively, when iodine is the electrophile, the product is the vinyl iodide 16. This can then be metallated and treated with a proton or a range of

  将化学计量的甲硅烷基-丙二烯7浓缩，然后直接用质子，一系列碳亲电子试剂和氯处理中间铜酸盐，得到乙烯基硅烷8-13。替代地，当碘是亲电子试剂时，产物是乙烯基碘16。然后可以将其金属化并用质子或一系列
• Preparation of a highly functionalized allylsilane for use in three-bond cascade reactions
  作者：Gregory J. Hollingworth、Thomas V. Lee、J.B. Sweeney

  DOI：10.1016/s0040-4039(00)61154-1

  日期：1992.9

  Preparation of the novel allylsilane, methyl 3-formyl-4-(phenyldimethylsilylmethyl)pent-4-enoate (2) was accomplished in 7 steps from 2,3-dibromopropene. (2) has great potential as an annulating reagent.