(E)-2,3-dimethyl-2,5-dodecadiene

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (E)-2,3-dimethyl-2,5-dodecadiene
• 英文别名: (E)-2,3-dimethyldodeca-2,5-diene；(5E)-2,3-dimethyldodeca-2,5-diene
• 化学式: C₁₄H₂₆
• 分子量: 194.36
• InChiKey: DEFPYAOWOPSAOO-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  14
• 可旋转键数：
  7
• 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

• 作为产物：
  描述：

  辛烯 、 2,3-二甲基-1,3-丁二烯 在 C₃₅H₃₈O₅P₂*Br₂Co 、 zinc(II) iodide 、 锌 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到(E)-2,3-dimethyl-2,5-dodecadiene
  参考文献：
  名称：

  Gaining Absolute Control of the Regiochemistry in the Cobalt-Catalyzed 1,4-Hydrovinylation Reaction

  摘要：

  The absolute control of the regiochemistry of a cobalt-catalyzed 1,4-hydrovinylation reaction is achieved by alternation of the ligands applied. While the dppe/dppp ligands led to the formation of the branched product, the herein described application of the SchmalzPhos ligand generates the corresponding linear product in both excellent yields and regioselectivities. The catalyst system exhibits a high tolerance toward functional groups, and the very mild reaction conditions allow the synthesis of 1,4-dienes without isomerization into conjugated systems.

  DOI：

  10.1021/ol202696n

文献信息

• Nickel-catalysed addition of organoboronates to 1,3-dienesElectronic supplementary information (ESI) available: 1H NMR spectra and MS data. See http://www.rsc.org/suppdata/cc/b2/b207185a/
  作者：Eiji Shirakawa、Go Takahashi、Teruhisa Tsuchimoto、Yusuke Kawakami

  DOI：10.1039/b207185a

  日期：2002.9.23

  Aryl- and alkenylboronates were found to add to 1,3-dienes in the presence of a catalytic amount of bis(1,5-cyclooctadiene)nickel, where a proton source in combination with a solvent considerably controls the regioselectivity.

  在双(1,5-环辛二烯)镍的催化下，发现芳基和烯基硼酸盐可与 1,3-二烯相加，其中质子源与溶剂的结合在很大程度上控制了区域选择性。
• Gaining Absolute Control of the Regiochemistry in the Cobalt-Catalyzed 1,4-Hydrovinylation Reaction
  作者：Marion Arndt、Mehmet Dindaroğlu、Hans-Günther Schmalz、Gerhard Hilt

  DOI：10.1021/ol202696n

  日期：2011.12.2

  The absolute control of the regiochemistry of a cobalt-catalyzed 1,4-hydrovinylation reaction is achieved by alternation of the ligands applied. While the dppe/dppp ligands led to the formation of the branched product, the herein described application of the SchmalzPhos ligand generates the corresponding linear product in both excellent yields and regioselectivities. The catalyst system exhibits a high tolerance toward functional groups, and the very mild reaction conditions allow the synthesis of 1,4-dienes without isomerization into conjugated systems.