(6-iodo-2-hexenyl)trimethylsilane | 115142-37-5

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: (6-iodo-2-hexenyl)trimethylsilane
• 英文别名: (6-iodohex-2-enyl)trimethylsilane；6-iodo-1-trimethylsilyl-2-hexene；6-iodohex-2-enyl(trimethyl)silane
• CAS: 115142-37-5
• 化学式: C₉H₁₉ISi
• 分子量: 282.24
• InChiKey: ZYPKFDWSEBUMOK-UHFFFAOYSA-N

物化性质

• 沸点：
  231.3±33.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  (6-iodo-2-hexenyl)trimethylsilane 在 2,6-二叔丁基-4-甲基吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 4-methyl-1-(6-(trimethylsilyl)hex-4-enyl)pyridinium trifluoromethanesulfonate
  参考文献：
  名称：

  通过连续的亲核环化快速组装喹oli嗪类化合物到活化的酰胺上

  摘要：

  报道了一种新的合成喹喔啉的方法，该方法涉及由化学选择性酰胺活化引发的一系列亲核环化反应。特别注意了拴系亲核试剂的性质对级联反应的影响。结果，简单的无环酰胺可快速进入在环连接处带有叔或季中心的官能化喹嗪。在几种生物碱中发现了这种稠合的双环基序。

  DOI：

  10.1021/ol201616k
• 作为产物：
  描述：

  6-t-butyldimethylsiloxy-1-trimethylsilyl-2-hexene 在 4-甲基苯磺酸吡啶 、 三乙胺 、 sodium iodide 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 44.0h， 生成 (6-iodo-2-hexenyl)trimethylsilane
  参考文献：
  名称：

  Generation of the Dihydro-5H-Thiazolo[3,2-a]pyridin-3-one Ring System by Proton Loss from Isothiomünchnones

  摘要：

  Dihydro-5H-thiazolo[3,2-a]pyridin-3-ones are easily generated by proton loss from isothiomunchnones. The closely related tetrahydro-2H-pyrido[2,1-b]-[1,3]thiazin-4-one ring system was prepared by treating piperidine-2-thione with acryloyl chloride. These cyclic S,N-ketene acetals undergo smooth reaction with different electrophiles in the presence of Lewis acids.

  DOI：

  10.3987/com-93-s32

文献信息

• Highly Diastereoselective Synthesis of Substituted Pyrrolidines Using a Sequence of Azomethine Ylide Cycloaddition and Nucleophilic Cyclization
  作者：Guillaume Bélanger、Véronique Darsigny、Michaël Doré、François Lévesque

  DOI：10.1021/ol902767b

  日期：2010.4.2

  adducts, we successfully tuned the mechanistic path of a new reaction cascade to afford substituted pyrrolidines in high yields and diastereomeric purity. This was achieved by forcing the demetalation of tin- or silicon-substituted iminium ions, followed by azomethine ylide cycloaddition and nucleophilic cyclization. Structural complexity is thus built rapidly in a fully controlled one-pot reaction cascade

  尽管偶氮甲亚烷基的环加成反应通常会提供内/外加合物的混合物，但我们成功地调节了新反应级联的机理，从而以高收率和非对映体纯度提供了取代的吡咯烷。这是通过迫使锡或硅取代的亚胺离子脱金属，然后进行甲亚胺叶立德环加成和亲核环化来实现的。因此，在完全受控的一锅反应级联反应中，迅速建立了结构复杂性。
• Intramolecular Cyclization of Tethered Phenyl Ketones. Complementary Stereochemical Results Arising from the Indium-Promoted Ring Closure of Allyl Bromides and the Fluoride Ion-Induced Desilylation of Allylsilanes
  作者：Leo A. Paquette、José L. Mendez-Andino

  DOI：10.1021/jo981683s

  日期：1998.11.1

  dThe intramolecular indium-promoted cyclization of 4'-substituted (Z)- and (E)-7-bromo-5-heptenophenones has been examined in aqueous tetrahydrofuran. In every instance, ring closure occurred to deliver the syn-2-vinylcyclopentanol exclusively. The corresponding allylsilanes have been prepared as well, and the course of their fluoride ion-induced cyclization was also studied. In these systems, a kinetic bias for formation of the anti-2-vinylcyclopentanol is observed, although not with the same exclusivity. Accordingly, complementarity in product diastereoselectivity can be realized in purposeful fashion. The data acquired in this investigation suggest that the indium-catalyzed reactions involve intramolecularly coordinated transition states where development of a cis 5/6-bicyclic framework is most energetically feasible. In contrast, the silanes appear to utilize open-chain antiperiplanar transition states. While the latter are not particularly sensitive to double-bond geometry, they are responsive to steric compression involving the aryl group.
• Intramolecular cyclization of allyl- and propargylsilanes. The regio- and stereochemical outcome of the cyclization
  作者：Dieter Schinzer、Gerlinde Dettmer、Martin Ruppelt、Sandor Solyom、Juergen Steffen

  DOI：10.1021/jo00251a029

  日期：1988.8