6-iodo-3-methyl-1-hexene | 106815-04-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 英文名称: 6-iodo-3-methyl-1-hexene
• 英文别名: Qsifpxknyantbe-uhfffaoysa-；6-iodo-3-methylhex-1-ene
• CAS: 106815-04-7
• 化学式: C₇H₁₃I
• 分子量: 224.085
• InChiKey: QSIFPXKNYANTBE-UHFFFAOYSA-N

物化性质

• 沸点：
  85-87 °C(Press: 22 Torr)
• 密度：
  1.414±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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-3-methyl-1-hexene 在 六正丁基二锡 作用下， 以 苯 为溶剂， 反应 2.5h， 生成 1-(碘甲基)-2-甲基环戊烷
  参考文献：
  名称：

  Intramolecular Carbozincation of Unactivated Alkenes Occurs through a Zinc Radical Transfer Mechanism

  摘要：

  The cyclizations of a number of terminally unsaturated alkenyl zinc iodides to cyclopentylmethylzinc iodides, formerly believed to be nonradical in nature, have been revealed as radical chain cyclizations initiated by adventitious oxygen. Five cases are presented in which the published carbozincation cis/trans selectivities are essentially the same as those found for the cyclizations of the unsaturated alkyl iodide precursors of the, alkylzinc iodides by the iodine atom transfer method at approximately the same temperatures. In addition, it has been found that one of the organozinc cyclizations does not occur in a system in which oxygen has been rigorously excluded. The combined findings strongly suggest that these organozinc cyclizations occur by a zinc radical transfer mechanism rather than by a conventional carbometallation that is thought to occur with the analogous organolithium and organomagnesium cyclizations.

  DOI：

  10.1021/ja076554k
• 作为产物：
  描述：

  6-iodo-3-methyl-1-trimethylsilyl-1-hexyne 在 正己烷 、 二异丁基氢化铝 、 APTS 作用下， 以 乙醚 、 乙腈 为溶剂， 生成 6-iodo-3-methyl-1-hexene
  参考文献：
  名称：

  有机锌试剂的分子内碳金属化。

  摘要：

  伯或仲烯基锌的分子内环化反应在高度敏感的功能下，在完全区域特异性的5-exo-trig环化中导致环戊基甲基锌衍生物。

  DOI：

  10.1016/s0040-4020(01)85661-1

文献信息

• PhLi-initiated cycloisomerization of unsaturated organoiodides: mechanism of the isomerization of olefinic primary alkyl iodides
  作者：William F. Bailey、Matthew W. Carson

  DOI：10.1016/s0040-4039(99)01067-9

  日期：1999.7

  Evidence is presented indicating that the PhLi-initiated cycloisomerization of olefinic primary alkyl iodides involves a radical-mediated atom transfer process that had previously been implicated in the isomerization of secondary and tertiary substrates.

  证据表明，PhLi引发的烯烃伯烷基碘化物的环异构化涉及自由基介导的原子转移过程，该过程先前与仲和叔底物的异构化有关。
• Preparation and regiospecific cyclization of alkenyllithiums
  作者：William F. Bailey、Timo T. Nurmi、Jeffrey J. Patricia、Wei Wang

  DOI：10.1021/ja00242a032

  日期：1987.4
• Metal—halogen interchange between -butyllithium and 1-iodo-5-hexenes provides no evidence for single-electron transfer
  作者：William F Bailey、Jeffrey J Patricia、Timo T Nurmi、Wei Wang

  DOI：10.1016/s0040-4039(00)84395-6

  日期：1986.1
• Intramolecular Metallo-Ene-Allene Reactions. A New Carbocycles Synthesis
  作者：Christophe Meyer、Ilane Marek、Gilles Courtemanche、Jean-F. Normant

  DOI：10.1021/jo00109a017

  日期：1995.2

  Polysubstituted enynes have been lithiated on the propargylic position, and transmetalation to the corresponding zinc reagents promotes an easy cyclization reaction leading to polysubstituted cyclopentylmethylzinc derivatives. This cyclization is stereospecific, and a single diastereoisomer is formed, even when a tertiary and a quaternary center are linked in the process. The reaction is considered to take place via a metallo-ene-allene process.
• Intramolecular carbometallation of secondary organozinc reagents.
  作者：Christophe Meyer、Ilane Marek、Gilles Courtemanche、Jean-F. Normant

  DOI：10.1016/s0040-4039(00)61725-2

  日期：1993.9

  The intramolecular carbocyclization of secondary organozinc derivatives allows the preparation of cis-substituted cyclopentylmethylzinc derivatives in an easy and straightforward way.

表征谱图