2-methyl-1,7-octadiene | 13151-07-0

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 2-methyl-1,7-octadiene
• 英文别名: 2-methylocta-1,7-diene
• CAS: 13151-07-0
• 化学式: C₉H₁₆
• 分子量: 124.226
• InChiKey: GRMXFZGBPICEAU-UHFFFAOYSA-N

物化性质

• 保留指数：
  850;850;857;857

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  2-methyl-1,7-octadiene 在 trans-dichlorobis(2,6-dibromphenoxy)oxotungsten(VI) 、 四乙基铅 作用下， 以 various solvent(s) 为溶剂， 反应 2.0h， 以84%的产率得到3-甲基-1-环己烯
  参考文献：
  名称：

  Practical catalyst for cyclic metathesis. Synthesis of functional and/or enantiopure cycloalkenes.

  摘要：

  The oxo-tungsten complex trans-WOCl2(OAr)(2) (Ar = 2,6-dibromophenyl) is prepared by reaction of WOCl4 with 2 equiv of 2,6-dibromophenol. A variety of nonconjugated dienes are cleanly cyclized to the corresponding cycloalkenes using 2 mol % of this catalyst in combination with 4 mol % of tetraethyllead. All three components of the catalyst system are commercially available. The catalytic reactions are typically complete in 1 h at 90 degrees C and allow the synthesis of chiral cycloalkenes with little or no loss in optical activity. For example, (R)- (S)-citronellene have been cyclized to the corresponding (R)- or (S)-3-methylcyclopentenes in 97% enantiomeric excess. The cyclization is compatible with a variety of functional groups including some eater, amide, and ether derivatives. Tri- (but not tetra-) substituted cycloalkenes could be prepared using this catalyst.

  DOI：

  10.1021/ja00140a015
• 作为产物：
  描述：

  6-碘-1-己烯 、 异丙烯基溴化镁 在 四甲基乙二胺 、 三氯化铁 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以35%的产率得到2-methyl-1,7-octadiene
  参考文献：
  名称：

  铁催化的卤代烷与烯基格氏试剂的交叉偶联。

  摘要：

  DOI：

  10.1002/anie.200702206

文献信息

• Practical catalyst for cyclic metathesis. Synthesis of functional and/or enantiopure cycloalkenes.
  作者：William A. Nugent、Jerald Feldman、Joseph C. Calabrese

  DOI：10.1021/ja00140a015

  日期：1995.9

  The oxo-tungsten complex trans-WOCl2(OAr)(2) (Ar = 2,6-dibromophenyl) is prepared by reaction of WOCl4 with 2 equiv of 2,6-dibromophenol. A variety of nonconjugated dienes are cleanly cyclized to the corresponding cycloalkenes using 2 mol % of this catalyst in combination with 4 mol % of tetraethyllead. All three components of the catalyst system are commercially available. The catalytic reactions are typically complete in 1 h at 90 degrees C and allow the synthesis of chiral cycloalkenes with little or no loss in optical activity. For example, (R)- (S)-citronellene have been cyclized to the corresponding (R)- or (S)-3-methylcyclopentenes in 97% enantiomeric excess. The cyclization is compatible with a variety of functional groups including some eater, amide, and ether derivatives. Tri- (but not tetra-) substituted cycloalkenes could be prepared using this catalyst.
• Iron-Catalyzed Cross-Coupling of Alkyl Halides with Alkenyl Grignard Reagents
  作者：Amandine Guérinot、Sébastien Reymond、Janine Cossy

  DOI：10.1002/anie.200702206

  日期：2007.8.27