1-lithio-1,2,3,4-tetrapropyl-1,3-butadiene | 720680-94-4

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1-lithio-1,2,3,4-tetrapropyl-1,3-butadiene
• CAS: 720680-94-4
• 化学式: C₁₆H₂₉Li
• 分子量: 228.347
• InChiKey: BQSBDGTWJXYLKH-VONVIWPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.54
• 重原子数：
  17.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  4-庚酮 、 1-lithio-1,2,3,4-tetrapropyl-1,3-butadiene 在 盐酸 作用下， 反应 0.5h， 以71%的产率得到(5Z,7E)-4,5,6,7-Tetrapropyl-undeca-5,7-dien-4-ol
  参考文献：
  名称：

  Concise synthesis of stereodefined dienols and cyclopentadienes via direct addition of 1-bromomagnesiobutadienes and 1-lithiobutadienes to carbonyl compounds

  摘要：

  Stereodefined all-cis substituted dienols could be readily prepared in excellent yields by the direct addition of 1-bromomagnesiobutadiene or 1-lithiobutadiene derivatives with aldehydes and ketones. Depending on the nature of substituents and workup procedures. multi-substituted cyclopentadienes could be also formed in high yields from these dienols. It is interesting to note that, unlike normal alkenyl magnesium bromides, these conjugated butadienyl magnesiumbromide reagents do not react with ketones. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.156
• 作为产物：
  描述：

  5,6-dipropyl-4-iododeca-(4Z,6E)-4,6-diene 在 叔丁基锂 作用下， 以 正戊烷 为溶剂， 反应 1.0h， 生成 1-lithio-1,2,3,4-tetrapropyl-1,3-butadiene
  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

• Acyl-Lithiation of Olefins:  Formation of Cyclopentenones from 1-Lithio-butadienes and CO
  作者：Qiuling Song、Zhiping Li、Jinglong Chen、Congyang Wang、Zhenfeng Xi

  DOI：10.1021/ol026977l

  日期：2002.12.1

  Intramolecular acyl-lithiation of C=C double bonds proceeds following carbonylation of 1-lithio-1,3-dienes with CO to afford 2- or 3-cyclopentenone derivatives in good to excellent yields after hydrolysis. Addition of electrophiles to the carbonylation reaction mixtures affords various multiply substituted cyclopentenones.