1,1-difluoro-3-(3-methylbutyl)nona-1,2-diene | 877080-75-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 1,1-difluoro-3-(3-methylbutyl)nona-1,2-diene
• 英文别名: Undecane, 5-(difluoroethenylidene)-2-methyl-
• CAS: 877080-75-6
• 化学式: C₁₄H₂₄F₂
• 分子量: 230.341
• InChiKey: NFMWKXWDNKBNNR-UHFFFAOYSA-N

物化性质

• 沸点：
  254.2±15.0 °C(Predicted)
• 密度：
  0.876±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-甲基-1-已炔 、 二溴二氟甲烷 、 己基溴化镁 在 正丁基锂 、 copper(I) bromide dimethylsulfide complex 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 1,1-difluoro-3-(3-methylbutyl)nona-1,2-diene
  参考文献：
  名称：

  Highly Regioselective Synthesis of gem-Difluoroallenes through Magnesium Organocuprate S_N2‘ Substitution

  摘要：

  [GRAPHICS]The reaction of gem-difluoropropargyl electrophiles with Grignard reagents is complicated by the inherent difficulty of executing nucleophilic substitutions on a CF2 group, and the facile formation of carbenoid intermediates arising from alpha-elimination of fluoride. In the presence of an excess amount of a copper salt, a Grignard reagent reacts with gem-difluoropropargyl bromide via an SINT mechanism to produce gem-difluoroallene in high yield. If desired, the resulting difluoroallene can undergo a second nucleophilic attack on the CF2 terminus to yield a trisubstituted monofluoroallene through an addition-elimination mechanism.

  DOI：

  10.1021/ol052816g

文献信息

• Highly Regioselective Synthesis of <i>gem</i>-Difluoroallenes through Magnesium Organocuprate S_N2‘ Substitution
  作者：Masayuki Mae、Jiyoung A. Hong、Bo Xu、Gerald B. Hammond

  DOI：10.1021/ol052816g

  日期：2006.2.1

  [GRAPHICS]The reaction of gem-difluoropropargyl electrophiles with Grignard reagents is complicated by the inherent difficulty of executing nucleophilic substitutions on a CF2 group, and the facile formation of carbenoid intermediates arising from alpha-elimination of fluoride. In the presence of an excess amount of a copper salt, a Grignard reagent reacts with gem-difluoropropargyl bromide via an SINT mechanism to produce gem-difluoroallene in high yield. If desired, the resulting difluoroallene can undergo a second nucleophilic attack on the CF2 terminus to yield a trisubstituted monofluoroallene through an addition-elimination mechanism.