(+/-)-1-[(1S,5R)-2-methyl-5-(1-methylvinyl)cyclohex-2-enyl]-4-methylbenzene | 376353-55-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+/-)-1-[(1S,5R)-2-methyl-5-(1-methylvinyl)cyclohex-2-enyl]-4-methylbenzene
• 英文别名: (+/-)-trans-2-methyl-3-(4-methylphenyl)-5-isopropenyl-1-cyclohexene；1-methyl-4-[(1R,5S)-2-methyl-5-prop-1-en-2-ylcyclohex-2-en-1-yl]benzene
• CAS: 376353-55-8
• 化学式: C₁₇H₂₂
• 分子量: 226.362
• InChiKey: NSXUNWGCXLOJAI-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 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：

  三乙氧基对苯甲基硅烷 、 (+)-(R,R)-cis-carveolbenzoate 在 四丁基氟化铵 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以84%的产率得到(+/-)-1-[(1S,5R)-2-methyl-5-(1-methylvinyl)cyclohex-2-enyl]-4-methylbenzene
  参考文献：
  名称：

  Palladium-Catalyzed Arylation of Allylic Benzoates Using Hypervalent Siloxane Derivatives

  摘要：

  Palladium-catalyzed cross-coupling of hypervalent arylsiloxane derivatives proceeded in good to excellent yields with allylic benzoates. Arylation occurred with complete inversion of configuration. The scope and limitations of this reaction, an alternative to the Stille coupling, is summarized.

  DOI：

  10.1021/jo010627f

文献信息

• Efficient Palladium-Catalyzed Nucleophilic Addition of Triorganoindium Reagents to Carbocyclic Derivatives
  作者：Lucas Baker、Thomas Minehan

  DOI：10.1021/jo0357162

  日期：2004.5.1

  Palladium (0)-catalyzed allylic substitution reactions employing triorganoindium reagents have been investigated. In situ generated vinyl- and arylindiums react with substituted and unsubstituted cyclohex-2-enyl esters in the presence of 1-3 mol % Pd-2(dba)(3) to produce vinyl- or arylcyclohexenes in moderate to excellent yields. The stereoselectivity of this process was also examined, and evidence is presented that the reaction proceeds with inversion of stereochemical configuration.
• Palladium-Catalyzed Arylation of Allylic Benzoates Using Hypervalent Siloxane Derivatives
  作者：Reuben Correia、Philip DeShong

  DOI：10.1021/jo010627f

  日期：2001.10.1

  Palladium-catalyzed cross-coupling of hypervalent arylsiloxane derivatives proceeded in good to excellent yields with allylic benzoates. Arylation occurred with complete inversion of configuration. The scope and limitations of this reaction, an alternative to the Stille coupling, is summarized.