1-(3-isopropylphenyl)adamantane | 183967-44-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3-isopropylphenyl)adamantane
• 英文别名: 1-(3-Propan-2-ylphenyl)adamantane
• CAS: 183967-44-4
• 化学式: C₁₉H₂₆
• 分子量: 254.415
• InChiKey: LBTLQDKXTYGDLS-UHFFFAOYSA-N

物化性质

• 沸点：
  336.2±12.0 °C(Predicted)
• 密度：
  1.023±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 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：

  1-吲哚金刚烷 、 (1s,5s)-9-(3-isopropylphenyl)-9-borabicyclo[3.3.1]nonane 在 lithium tert-butoxide 、 NiBr2*diglyme 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 异丁醇 、 环己烷 为溶剂， 反应 28.83h， 以61%的产率得到1-(3-isopropylphenyl)adamantane
  参考文献：
  名称：

  Nickel-Catalyzed Carbon–Carbon Bond-Forming Reactions of Unactivated Tertiary Alkyl Halides: Suzuki Arylations

  摘要：

  The first Suzuki cross-couplings of unactivated tertiary alkyl electrophiles are described. The method employs a readily accessible catalyst (NiBr2 center dot diglyme/4,4'-di-tert-butyl-2,2'-bipyridine, both commercially available) and represents the initial example of the use of a group 10 catalyst to cross-couple unactivated tertiary electrophiles to form C-C bonds. This approach to the synthesis of all-carbon quaternary carbon centers does not suffer from isomerization of the, alkyl group, in contrast with the umpolung strategy for this bond construction (cross-coupling of a tertiary alkylmetal with an aryl electrophile). Preliminary mechanistic studies are consistent with the generation of a radical intermediate along the reaction pathway.

  DOI：

  10.1021/ja311669p

文献信息

• Indium-Catalyzed Friedel-Crafts Alkylation of Monosubstituted Benzenes by 1-Bromoadamantane
  作者：Paul Mosset、René Grée

  DOI：10.1055/s-0032-1316909

  日期：——

  Indium salts such as InCl3 and InBr3 (ca. 1-5 mol%) efficiently catalyzed the Friedel-Crafts reaction of 1-bromoadamantane with benzene and monosubstituted benzenes to give 1-adamantyl benzenes. Indium bromide enabled faster reactions than indium chloride but the latter was more suitable in the case of halobenzenes.