1,4-dilithio-1,2,3,4-tetrapropyl-1,3-butaidiene | 643744-63-2

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: 1,4-dilithio-1,2,3,4-tetrapropyl-1,3-butaidiene
• 英文别名: 1,4-dilithio-1,2,3,4-tetrapropyl-1,3-butadiene；1,2,3,4-tetrapropyl-1,4-dilitho-1,3-diene
• CAS: 643744-63-2
• 化学式: C₁₆H₂₈Li₂
• 分子量: 234.28
• InChiKey: WYQZLRGJTQWAPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,4-dilithio-1,2,3,4-tetrapropyl-1,3-butaidiene 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 (2Z,4Z)-2,3,4,5-Tetrapropyl-hexa-2,4-diene-1,6-diol
  参考文献：
  名称：

  Concise synthesis of multiply substituted stereodefined cis,cis-2,4-diene-1,6-dials, cis,cis-2,4-diene-1,6-diols and further applications

  摘要：

  Reactions of 1,4-dilithio-1,3-dienes with DMF afforded multiply substituted stereodefined cis,cis-2,4-diene-1,6-dials in high yields. Treatment of these 1,6-dials with LiAlH4 or RLi resulted in the formation of their corresponding 1,6-diols. These bifunctional compounds, cis,cis-2,4-diene-1,6-dials and -1,6-diols are otherwise not readily available. Further reaction of these 1,6-diols with an aldehyde catalyzed by strong acids led to the formation of oxacycles of novel structures. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.003
• 作为产物：
  描述：

  (4Z,6Z)-5,6-dipropyl-4,7-diiododeca-4,6-diene 在 叔丁基锂 作用下， 反应 1.0h， 生成 1,4-dilithio-1,2,3,4-tetrapropyl-1,3-butaidiene
  参考文献：
  名称：

  Novel Cycloaddition of Nitriles with Monolithio- and Dilithiobutadienes

  摘要：

  Two novel and synthetically useful reaction patterns of organolithium compounds with nitriles are reported to afford pyridine derivatives as the final products. Both 1-lithio-1,3-dienes and 1,4-dilithio-1,3-dienes, which can be easily generated in situ by lithiation of their corresponding iodo compounds, react with nitriles in the presence of HMPA to form substituted pyridines including 2,2'-bipyridines and tetrahydroisoquinolines in high yields.

  DOI：

  10.1021/ja0262176

文献信息

• Formation of 2,6-dioxabicyclo[3.3.0]-octa-3,7-dienes or multiply substituted o-benzoquinones from reactions of 1,4-dilithio-1,3-dienes with dimethyl oxalate
  作者：Guoliang Mao、Jiang Lu、Zhenfeng Xi

  DOI：10.1016/j.tetlet.2004.08.181

  日期：2004.10

  Reactions of 1,4-dilithio-1,3-dienes with dimethyl oxalates afforded multiply substituted o-benzoquinones or stereodefined 2,6-dioxabicyclo[3.3.0]-octa-3,7-dienes in good yields.

  1，4-二硫代-1，3-二烯与草酸二甲酯的反应以良好的产率提供了多取代的邻苯并醌或立体定义的2，6-二恶双环[3.3.0]-八-3，7-二烯。
• Reaction of Dilithio Reagents with PhSiH₃: Formation of Siloles and 3-Silacyclopentenes
  作者：Baosheng Wei、Heng Li、Jianhao Yin、Wen-Xiong Zhang、Zhenfeng Xi

  DOI：10.1021/acs.joc.5b01595

  日期：2015.9.4

  The reaction chemistry between 1,4-dilithio-1,3-butadienes (dilithio reagents for short) and PhSiH3 has been investigated. Direct substitution of two hydride ions from PhSiH3 with the dilithio reagents led to multisubstituted siloles (silacyclopentadienes) in diethyl ether solution, with the concomitant generation of LiH. When THF was used as the solvent, the reaction between PhSiH3 and 1,4-bis(silyl)

  研究了1,4-二硫代-1,3-丁二烯（简称二硫代试剂）与PhSiH 3之间的反应化学。用二硫代试剂直接取代PhSiH 3中的两个氢化物离子，在乙醚溶液中产生多取代的硅环（硅环戊二烯），并伴随生成LiH。当使用THF作为溶剂时，PhSiH 3与1，4-双（甲硅烷基）二硫代试剂之间的反应立体地提供了顺式-3-硅杂环戊烯。实验结果表明，反应体系中原位生成了反应性LiH。LiH正式合成加成到硅杂环戊二烯中间体中将提供硅杂环戊烯，最有可能通过五价有机硅酸盐来实现。
• Stereoselective Synthesis of Polysubstituted 2,5-Dihydrofurans from Reaction of 1,4-Dilithio-1,3-dienes with Aldehydes
  作者：Jinglong Chen、Qiuling Song、Pixu Li、Hairong Guan、Xianglin Jin、Zhenfeng Xi

  DOI：10.1021/ol0261478

  日期：2002.6.1

  Reaction of 1,4-dilithio-1,3-diene derivatives with 2 equiv of aldehydes affords polysubstituted 2,5-dihydrofurans in good to high yields with perfect regio- and stereoselectivities. Hexa-2,4-diene-1,6-dialcoholates are proposed as the first intermediates, which undergo a cyclization and subsequent elimination of Li2O to generate the 2,5-dihydrofuran derivatives.
• Diazo Compounds as Electrophiles To React with 1,4-Dilithio-1,3-dienes: Efficient Synthesis of 1-Imino-pyrrole Derivatives
  作者：Ming Zhan、Shaoguang Zhang、Wen-Xiong Zhang、Zhenfeng Xi

  DOI：10.1021/ol401878q

  日期：2013.8.16

  1-Imino-pyrrole and indole derivatives were synthesized in high yields from the reaction of diaryl diazomethanes with 1,4-dilithio-1,3-dienes. Diaryl diazomethanes reacted as electrophiles in this reaction. An unprecedented Zn-complex was formed via transmetalation of the above reaction intermediate with ZnCl2 and was structurally characterized. The trans-mu(2)-eta(1):eta(1) coordination mode in the solid state for this azaallylzinc compound was observed.
• Deoxygenative Cycloaddition of Aldehydes with Alkynes Mediated by AlCl3 and Zirconium: Formation of Cyclopentadiene Derivatives
  作者：Zhenfeng Xi、Pixu Li

  DOI：10.1002/1521-3773(20000818)39:16<2950::aid-anie2950>3.0.co;2-y

  日期：2000.8.18