(3Z,5E)-4,5-diethyl-3-iodoocta-3,5-diene | 193211-59-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (3Z,5E)-4,5-diethyl-3-iodoocta-3,5-diene
• 英文别名: 4,5-diethyl-3-iodoocta-(3Z,5E)-3,5-diene
• CAS: 193211-59-5
• 化学式: C₁₂H₂₁I
• 分子量: 292.203
• InChiKey: AATQCHYUBOFPNI-PVHUKWJHSA-N

物化性质

• 沸点：
  296.0±9.0 °C(Predicted)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (3Z,5E)-4,5-diethyl-3-iodoocta-3,5-diene 在 盐酸 、 叔丁基锂 作用下， 以 乙醚 、 正戊烷 为溶剂， 反应 21.0h， 生成
  参考文献：
  名称：

  多取代二烯酰胺的合成及其亲电环化反应生成环状氨基醚

  摘要：

  可以通过将1-硫代丁二烯衍生物直接加到异氰酸N-芳基酯和N-烷基N-烷基酯上来简明地以高收率制备立体确定的多取代的二烯酰胺。这些二烯酰胺的亲电环化反应以极好的收率和完美的选择性生成了取代的环状亚氨基醚。当用12 N HCl水溶液处理时，二烯酰胺经过有效且选择性的亲电环化，得到环状亚氨酸酯衍生物。当用NBS处理时，形成单溴或双溴的环状亚氨基醚。

  DOI：

  10.1021/jo050433q
• 作为产物：
  描述：

  3-己炔 在 正丁基锂 、 二氯二茂锆 、 碘 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以90%的产率得到(3Z,5E)-4,5-diethyl-3-iodoocta-3,5-diene
  参考文献：
  名称：

  Selective one carbon-carbon bond formation reaction of zirconacyclopentadienes with aryl iodides or alkynyl iodides

  摘要：

  Reaction of zirconacyclopentadienes with one equiv or two equiv of aryl iodides in the presence of CuCl and DMPU afforded mono-arylated diene derivatives in high yields with high selectivities. Treatment of zirconacyclopentadienes with one equiv of 2-thienyl iodide similarly gave thienyldienes in the presence of CuCl and DMPU, whereas the reaction with two equiv of 2-thienyl iodide produced thienyl iododiene derivatives in high yields. Zirconacyclopentadienes reacted with two equiv of alkynyl iodides to give iododienynes in good yields in the presence of CuCl. This is in sharp contrast to the reaction with two equiv of alkynyl iodides in the presence of CuCl and DMPU which provides dienediynes. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10295-2

文献信息

• Unique reactivity of a 1,4-dilithiobutadiene with methyl iodide
  作者：Paul F. Hudrlik、Donghua Dai、Anne M. Hudrlik

  DOI：10.1016/j.tetlet.2006.03.067

  日期：2006.5

  4-dilithiobutadiene 5 with MeI in THF gave predominantly methyl iododiene 6. Monolithio monoiodo intermediate 8 was shown not to be involved in the formation of 6, but the results were consistent with the involvement of monolithio monomethyl intermediate 11, which could lead to 6 by metal–halogen exchange. Several other lithioalkenes also reacted with MeI to give alkenyl iodides.

  1,4-二硫代丁二烯5与MeI在THF中的反应主要产生甲基碘二烯6。单硫代单碘中间体8被证明不参与6的形成，但结果与单硫代单甲基中间体11的参与一致，后者可能通过金属-卤素交换而生成6。其他几种硫代烯烃也与MeI反应生成烯基碘化物。
• Reaction of 4-methyl, 4-phenyl, and 4-hydrogen substituted 1-lithio-1,3-butadienes with aldehydes: preparation of multiply substituted cyclopentadienes
  作者：Zhihui Wang、Hongyun Fang、Zhenfeng Xi

  DOI：10.1016/j.tet.2006.04.083

  日期：2006.7

  acidic solution. Reaction mechanism study revealed that these cyclopentadienes were formed via an acid-promoted cyclization of conjugated dienols. Thus, stereodefined all-cis substituted dienols or a wide diversity of substituted cyclopentadienes can be obtained from the same 1-lithio-1,3-butadiene reagent and aldehyde by adjusting the hydrolysis conditions.

  研究了醛与丁二烯基骨架第4位上具有甲基，苯基或氢取代基的1-lithio-1,3-丁二烯试剂的反应。使用强酸性溶液水解后，可以高收率获得多取代的环戊二烯衍生物。反应机理研究表明，这些环戊二烯是通过酸促进的共轭二烯醇环化反应形成的。因此，可以通过调节水解条件，从相同的1-硫代-1,3-丁二烯试剂和醛中获得立体定义的顺式取代的二烯醇或种类繁多的取代的环戊二烯。
• Domino N−H/C−H Bond Activation: Copper-Catalyzed Synthesis of Nitrogen-Bridgehead Heterocycles Using Azoles and 1,4-Dihalo-1,3-dienes
  作者：Qian Liao、Liyun Zhang、Shutao Li、Chanjuan Xi

  DOI：10.1021/ol1026365

  日期：2011.1.21

  Copper-catalyzed tandem coupling of 1,4-dihalo-1,3-dienes with azoles via an N-H bond and its adjacent C-H bond activation has been described. The reaction exhibits good regioselectivity when unsymmetrical 1,4-dihalo-1,3-diene is employed. This method provided a novel route to the synthesis of nitrogen-bridgehead azolopyridine derivatives.
• Remarkable effect of copper chloride on diiodination of zirconacyclopentadienes
  作者：Chanjuan Xi、Shouquan Huo、Tarek Hassan Afifi、Ryuichiro Hara、Tamotsu Takahashi

  DOI：10.1016/s0040-4039(97)00835-6

  日期：1997.6

  Treatment of zirconacyclopentadienes with two equiv of iodine in THF in the presence of 1.0 equiv of CuCl gave diiododienes in good to high yields without formation of monoiododienes. This is in sharp contrast to the case without CuCl which afforded monoiododienes as major products. For zirconacyclopentenes. CuCl was also effective but the use of ICl was more practical. When zirconacyclopentenes were treated with 2 equiv of ICl, only diiodination products were formed. Preparation of silacyclopentadienes or spiro compounds using the diidodienes was demonstrated. (C) 1997 Elsevier Science Ltd.
• Preparation and Electrophilic Cyclization of Multisubstituted Dienamides Leading to Cyclic Iminoethers
  作者：Congyang Wang、Jiang Lu、Guoliang Mao、Zhenfeng Xi

  DOI：10.1021/jo050433q

  日期：2005.6.1

  Stereodefined multisubstituted dienamides could be concisely prepared in high yields by direct addition of 1-lithiobutadiene derivatives to both N-aryl and N-alkyl isocyanates. Electrophilic cyclization of these dienamides was achieved to generate substituted cyclic iminoethers in excellent yields with perfect selectivity. When treated with 12 N aqueous HCl, dienamides underwent efficient and selective

  可以通过将1-硫代丁二烯衍生物直接加到异氰酸N-芳基酯和N-烷基N-烷基酯上来简明地以高收率制备立体确定的多取代的二烯酰胺。这些二烯酰胺的亲电环化反应以极好的收率和完美的选择性生成了取代的环状亚氨基醚。当用12 N HCl水溶液处理时，二烯酰胺经过有效且选择性的亲电环化，得到环状亚氨酸酯衍生物。当用NBS处理时，形成单溴或双溴的环状亚氨基醚。