(((5-(2-methylcyclopentyl)pentyl)oxy)methyl)benzene | 1043905-82-3

• 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: (((5-(2-methylcyclopentyl)pentyl)oxy)methyl)benzene
• 英文别名: 5-(2-Methylcyclopentyl)pentoxymethylbenzene
• CAS: 1043905-82-3
• 化学式: C₁₈H₂₈O
• 分子量: 260.42
• InChiKey: JKHOXNDXGCJYQX-UHFFFAOYSA-N

物化性质

• 沸点：
  344.2±11.0 °C(Predicted)
• 密度：
  0.932±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  O-(11-phenylmethoxyundec-1-en-6-yl) methylsulfanylmethanethioate 在 偶氮二异丁腈 、 2-苯基-1,2,4-三唑-3-亚基硼烷 作用下， 以 苯 为溶剂， 反应 2.0h， 以67%的产率得到(((5-(2-methylcyclopentyl)pentyl)oxy)methyl)benzene
  参考文献：
  名称：

  Complexes of Borane and N-Heterocyclic Carbenes: A New Class of Radical Hydrogen Atom Donor

  摘要：

  Calculations suggest that complexes of borane with N-heterocyclic carbenes (NHC) have B-H bond dissocation energies more then 20 Kcal/mol less than free borane, diborane, borane-THF, and related complexes. Values are in the range of popular radical hydrogen atom donors like tin hydrides (70-80 Kcal/mol). The resulting prediction that NHC borane complexes could be used as radical hydrogen atom donors was verified by radical deoxygenations of xanthates by using either AIBN or triethylborane as initiator.

  DOI：

  10.1021/ja804150k

文献信息

• Radical Deoxygenation of Xanthates and Related Functional Groups with New Minimalist N-Heterocyclic Carbene Boranes
  作者：Shau-Hua Ueng、Louis Fensterbank、Emmanuel Lacôte、Max Malacria、Dennis P. Curran

  DOI：10.1021/ol101015m

  日期：2010.7.2

  Minimalist N-heterocyclic carbene boranes 1,3-dimethylimidazol-2-ylideneborane and 2,4-dimethyl-1,2,4-triazol-3-ylideneborane are readily available and have low molecular weights. They exhibit superior performance to first-generation NHC−boranes, providing improved yields in reductions of xanthates and related functional groups.

  极简主义的N-杂环卡宾硼烷1,3-二甲基咪唑-2-亚基硼烷和2,4-二甲基-1,2,4-三唑-3-亚基硼烷很容易获得，并且分子量低。它们表现出优于第一代NHC-硼烷的性能，在减少黄药和相关官能团方面提供了更高的收率。
• Polarity Reversal Catalysis in Radical Reductions of Halides by N-Heterocyclic Carbene Boranes
  作者：Xiangcheng Pan、Emmanuel Lacôte、Jacques Lalevée、Dennis P. Curran

  DOI：10.1021/ja300416f

  日期：2012.3.28

  ineffective radical reductions of alkyl and aryl halides by N-heterocyclic carbene boranes (NHC-boranes) are catalyzed by thiols. Reductions and reductive cyclizations with readily available 1,3-dimethylimidazol-2-ylidene borane and a water-soluble triazole relative are catalyzed by thiophenol and tert-dodecanethiol [C(9)H(19)C(CH(3))(2)SH]. Rate constants for reaction of the phenylthiyl (PhS•) radical with

  否则，N-杂环卡宾硼烷（NHC-硼烷）对烷基和芳基卤化物的缓慢或完全无效的自由基还原由硫醇催化。使用容易获得的 1,3-二甲基咪唑-2-亚基硼烷和水溶性三唑相关物的还原和还原环化反应由苯硫酚和叔十二烷硫醇催化 [C(9)H(19)C(CH(3))(2 )SH]。苯硫基 (PhS•) 自由基与两个 NHC 硼烷反应的速率常数已通过激光闪光光解实验测量为 ~10(8) M(-1) s(-1)。对现有证据的分析表明极性反转催化的作用。