3,3-dimethyl-1,7-octadiene | 90976-02-6

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 3,3-dimethyl-1,7-octadiene
• 英文别名: 3,3-Dimethylocta-1,7-diene
• CAS: 90976-02-6
• 化学式: C₁₀H₁₈
• 分子量: 138.253
• InChiKey: YHYNARHCKLRVIG-UHFFFAOYSA-N

物化性质

• 沸点：
  150.3±10.0 °C(Predicted)
• 密度：
  0.752±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  3,3-dimethyl-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 1.0h， 以87%的产率得到6,6-dimethylcyclohexadiene
  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：

  5-溴-1-戊烯 、 1-溴-3-甲基-2-丁烯 在 copper(l) cyanide 、 magnesium 作用下， 生成 3,3-dimethyl-1,7-octadiene
  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

文献信息

• Selective hydrogenation of substituted dienes catalyzed by an organoyttrium complex
  作者：Gary A. Molander、John O. Hoberg

  DOI：10.1021/jo00038a004

  日期：1992.6

  Cp*2YMe(THF) has been developed as an efficient catalyst for the selective reduction of substituted dienes.